PMID-sentid	Pub_year	Sent_text	compound_name	comp_offset	prot_official_name	organism	prot_offset
17603178-0	2007	Lignans and coumarins from the roots of Anthriscus sylvestris and their increase of caspase-3 activity in HL-60 cells.	Coumarins	12-21	caspase 3	Homo sapiens	84-93
17849045-3	2007	The identification of the molecular target of coumarins, VKORC1, has greatly improved the understanding of coumarin treatment and illuminated new perspectives for a safer and more individualized oral anticoagulation therapy.	Coumarins	46-55	vitamin K epoxide reductase complex subunit 1	Homo sapiens	57-63
17599282-0	2007	Effect of chrysin and natural coumarins on UGT1A1 and 1A6 activities in rat and human hepatocytes in primary culture.	Coumarins	30-39	UDP glucuronosyltransferase family 1 member A1	Rattus norvegicus	43-57
17635701-0	2007	VKORC1: molecular target of coumarins.	Coumarins	28-37	vitamin K epoxide reductase complex subunit 1	Homo sapiens	0-6
17635701-2	2007	VKORC1 is the key enzyme of the vitamin K cycle and the molecular target of coumarins, which represent the most commonly prescribed drugs for therapy and prevention of thromboembolic conditions.	Coumarins	76-85	vitamin K epoxide reductase complex subunit 1	Homo sapiens	0-6
17599282-5	2007	After 3 days of treatment at a concentration of 25 microM, the pyranocoumarins avicennin and CIS-avicennol, and the furocoumarins bergapten and imperatorin, increased by 2-fold UGT1A1-dependent activity, equivalent to the increases obtained with chrysin at 25 microM, whereas in the presence of the simple coumarins such as coumarin or umbelliferone, UGT1A1-dependent activity was not modified.	Coumarins	69-78	UDP glucuronosyltransferase family 1 member A1	Homo sapiens	177-183
17599282-4	2007	In the present study, the effects of the flavone chrysin and six natural coumarins isolated from various Rutaceous plants on UGT1A6-dependent P-nitrophenol and/or UGT1A1-dependent bilirubin glucuronoconjugation activities were evaluated in cultured rat and human hepatocytes and compared to those of the prototypical UGT1A inducers beta-naphthoflavone, phenobarbital and clofibric acid.	Coumarins	73-82	UDP glucuronosyltransferase family 1 member A6	Rattus norvegicus	125-131
17599282-5	2007	After 3 days of treatment at a concentration of 25 microM, the pyranocoumarins avicennin and CIS-avicennol, and the furocoumarins bergapten and imperatorin, increased by 2-fold UGT1A1-dependent activity, equivalent to the increases obtained with chrysin at 25 microM, whereas in the presence of the simple coumarins such as coumarin or umbelliferone, UGT1A1-dependent activity was not modified.	Coumarins	69-78	UDP glucuronosyltransferase family 1 member A1	Homo sapiens	351-357
17599282-6	2007	In terms of structural requirements for UGT1A1 induction, the present study suggests that the B-ring (phenyl) for chrysin and the furan or pyran rings for coumarins are essential for the biological activity.	Coumarins	155-164	UDP glucuronosyltransferase family 1 member A1	Homo sapiens	40-46
17599282-4	2007	In the present study, the effects of the flavone chrysin and six natural coumarins isolated from various Rutaceous plants on UGT1A6-dependent P-nitrophenol and/or UGT1A1-dependent bilirubin glucuronoconjugation activities were evaluated in cultured rat and human hepatocytes and compared to those of the prototypical UGT1A inducers beta-naphthoflavone, phenobarbital and clofibric acid.	Coumarins	73-82	UDP glucuronosyltransferase family 1 member A1	Rattus norvegicus	163-169
17599282-4	2007	In the present study, the effects of the flavone chrysin and six natural coumarins isolated from various Rutaceous plants on UGT1A6-dependent P-nitrophenol and/or UGT1A1-dependent bilirubin glucuronoconjugation activities were evaluated in cultured rat and human hepatocytes and compared to those of the prototypical UGT1A inducers beta-naphthoflavone, phenobarbital and clofibric acid.	Coumarins	73-82	UDP glucuronosyltransferase family 1 member A complex locus	Homo sapiens	125-130
17073630-7	2006	Furthermore, several synthetic coumarins with a variety of pharmacophoric groups at C-3, C-4 and C-7 positions have been intensively screened for anti-microbial, anti-HIV, anti-cancer, lipid-lowering, anti-oxidant, and anti-coagulation activities.	Coumarins	31-40	complement C3	Homo sapiens	84-87
16824763-0	2006	Structure-activity relationship of natural and synthetic coumarins inhibiting the multidrug transporter P-glycoprotein.	Coumarins	57-66	ATP binding cassette subfamily B member 1	Homo sapiens	104-118
16824763-1	2006	A set of 32 natural and synthetic coumarins were tested in order to evaluate their activity on human leukemic cells (K562/R7) overexpressing P-glycoprotein (P-gp).	Coumarins	34-43	ATP binding cassette subfamily B member 1	Homo sapiens	141-155
16824763-1	2006	A set of 32 natural and synthetic coumarins were tested in order to evaluate their activity on human leukemic cells (K562/R7) overexpressing P-glycoprotein (P-gp).	Coumarins	34-43	ATP binding cassette subfamily B member 1	Homo sapiens	157-161
16879214-1	2006	BACKGROUND: Vitamin K epoxide reductase (VKORC1) is the site of inhibition by coumarins.	Coumarins	78-87	vitamin K epoxide reductase complex subunit 1	Homo sapiens	12-39
16879214-1	2006	BACKGROUND: Vitamin K epoxide reductase (VKORC1) is the site of inhibition by coumarins.	Coumarins	78-87	vitamin K epoxide reductase complex subunit 1	Homo sapiens	41-47
16413781-0	2006	Investigation of mechanism-based thrombin inhibitors: Implications of a highly conserved water molecule for the binding of coumarins within the S pocket.	Coumarins	123-132	coagulation factor II, thrombin	Homo sapiens	33-41
17691945-3	2007	Coumarins and cyclothialidines are natural products that inhibit the ATPase activity of DNA gyrase by blocking the binding of ATP to subunit GyrB.	Coumarins	0-9	DNA topoisomerase II alpha	Homo sapiens	88-98
16964755-8	2006	Among the compounds isolated from this plant, the five coumarins as well as the three flavonoids showed COX-2/5-LOX dual inhibitory activity.	Coumarins	55-64	prostaglandin-endoperoxide synthase 2	Mus musculus	104-109
16964755-8	2006	Among the compounds isolated from this plant, the five coumarins as well as the three flavonoids showed COX-2/5-LOX dual inhibitory activity.	Coumarins	55-64	arachidonate 5-lipoxygenase	Mus musculus	110-115
16739070-11	2006	To our knowledge, this is the first report identifying sesquiterpene coumarins from Ferula as possible drug candidates for the reversion of MDR encoded by the MDR1 gene or the synthesis of agents probing Pgp.	Coumarins	69-78	ATP binding cassette subfamily B member 1	Canis lupus familiaris	159-163
16739070-11	2006	To our knowledge, this is the first report identifying sesquiterpene coumarins from Ferula as possible drug candidates for the reversion of MDR encoded by the MDR1 gene or the synthesis of agents probing Pgp.	Coumarins	69-78	PGP	Canis lupus familiaris	204-207
16464579-0	2006	Substituted coumarins as potent 5-lipoxygenase inhibitors.	Coumarins	12-21	arachidonate 5-lipoxygenase	Homo sapiens	32-46
17073630-7	2006	Furthermore, several synthetic coumarins with a variety of pharmacophoric groups at C-3, C-4 and C-7 positions have been intensively screened for anti-microbial, anti-HIV, anti-cancer, lipid-lowering, anti-oxidant, and anti-coagulation activities.	Coumarins	31-40	complement C4A (Rodgers blood group)	Homo sapiens	89-92
17073630-7	2006	Furthermore, several synthetic coumarins with a variety of pharmacophoric groups at C-3, C-4 and C-7 positions have been intensively screened for anti-microbial, anti-HIV, anti-cancer, lipid-lowering, anti-oxidant, and anti-coagulation activities.	Coumarins	31-40	complement C7	Homo sapiens	97-100
15809436-2	2005	NQO1 binds and stabilizes WT p53, whereas NQO1 inhibitors including dicoumarol and various other coumarins and flavones induce ubiquitin-independent proteasomal p53 degradation and thus inhibit p53-induced apoptosis.	Coumarins	97-106	NAD(P)H quinone dehydrogenase 1	Homo sapiens	42-46
17124101-4	2006	Patients with either of two common variants, CYP2C9*2 or CYP2C9*3, metabolize coumarins slowly and are twice as likely to have a laboratory or clinical adverse event, unless their initial coumarin doses are reduced.	Coumarins	78-87	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	45-51
17124101-4	2006	Patients with either of two common variants, CYP2C9*2 or CYP2C9*3, metabolize coumarins slowly and are twice as likely to have a laboratory or clinical adverse event, unless their initial coumarin doses are reduced.	Coumarins	78-87	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	57-63
16507510-2	2006	Phytochemicals including cinnamic acid derivatives, various classes of flavonoids and coumarins were tested for the inhibitory activity on NAT1 and NAT2 from human liver and the human cholangiocarcinoma cell line: KMBC cells.	Coumarins	86-95	N-acetyltransferase 1	Homo sapiens	139-143
16507510-2	2006	Phytochemicals including cinnamic acid derivatives, various classes of flavonoids and coumarins were tested for the inhibitory activity on NAT1 and NAT2 from human liver and the human cholangiocarcinoma cell line: KMBC cells.	Coumarins	86-95	N-acetyltransferase 2	Homo sapiens	148-152
16302799-1	2005	In this work, coumarins were screened on thrombin (THR) and factor Xa (FXa), two of the most promising targets for the development of anticoagulant drugs.	Coumarins	14-23	coagulation factor II, thrombin	Homo sapiens	41-49
16302799-1	2005	In this work, coumarins were screened on thrombin (THR) and factor Xa (FXa), two of the most promising targets for the development of anticoagulant drugs.	Coumarins	14-23	coagulation factor II, thrombin	Homo sapiens	51-54
16302799-1	2005	In this work, coumarins were screened on thrombin (THR) and factor Xa (FXa), two of the most promising targets for the development of anticoagulant drugs.	Coumarins	14-23	coagulation factor X	Homo sapiens	60-69
16302799-1	2005	In this work, coumarins were screened on thrombin (THR) and factor Xa (FXa), two of the most promising targets for the development of anticoagulant drugs.	Coumarins	14-23	coagulation factor X	Homo sapiens	71-74
16137881-5	2005	Two coumarins were also Tat antagonists and the presence of both activities correlated with a stronger inhibition of HIV replication.	Coumarins	4-13	tyrosine aminotransferase	Homo sapiens	24-27
15961979-2	2005	Because CYP2C9 is a genetically polymorphic enzyme, genetic variability could play an important role in the potential interaction between NSAIDs and coumarins.	Coumarins	149-158	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	8-14
16199156-6	2005	Molecular modeling studies suggest that these coumarins bind to an allosteric site in the inactive conformation of MEK1.	Coumarins	46-55	mitogen-activated protein kinase kinase 1	Homo sapiens	115-119
16199156-9	2005	Our findings have therefore raised the possibility that other naturally occurring or synthetic coumarins with anti-cancer and anti-inflammatory activities might exert their biological function through the inhibition of MEK1.	Coumarins	95-104	mitogen-activated protein kinase kinase 1	Homo sapiens	219-223
16235922-1	2005	[structure: see text] We have developed a general and efficient approach to a diverse series of phosphacoumarins as analogues of coumarins with various biological activities, and the inhibitory activity of the synthesized phosphacoumarins against the enzyme SHP-1, a protein tyrosine phosphatases, was tested.	Coumarins	103-112	protein tyrosine phosphatase non-receptor type 6	Homo sapiens	258-263
15809436-2	2005	NQO1 binds and stabilizes WT p53, whereas NQO1 inhibitors including dicoumarol and various other coumarins and flavones induce ubiquitin-independent proteasomal p53 degradation and thus inhibit p53-induced apoptosis.	Coumarins	97-106	tumor protein p53	Homo sapiens	161-164
15809436-2	2005	NQO1 binds and stabilizes WT p53, whereas NQO1 inhibitors including dicoumarol and various other coumarins and flavones induce ubiquitin-independent proteasomal p53 degradation and thus inhibit p53-induced apoptosis.	Coumarins	97-106	tumor protein p53	Homo sapiens	161-164
15665333-0	2005	Kinetic analysis of oxidation of coumarins by human cytochrome P450 2A6.	Coumarins	33-42	cytochrome P450 family 2 subfamily A member 6	Homo sapiens	52-71
14760217-1	2003	Warfarin and other coumarins are metabolized by the cytochrome P450 2C9 complex.	Coumarins	19-28	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	52-71
14993815-1	2004	To investigate the structure-activity relationship of coumarins for the inhibitory activity on mushroom tyrosinase, the 50% inhibitory concentration (IC50 values) of 18 coumarins and four cinnamic acid derivatives were measured.	Coumarins	54-63	tyrosinase	Mus musculus	104-114
15358790-10	2004	These results demonstrate that coumarins (a common type of phytochemical) or their derivatives can be potent inhibitors of aromatase and may be useful in suppressing aromataseand ER-positive breast tumors.	Coumarins	31-40	cytochrome P450 family 19 subfamily A member 1	Homo sapiens	123-132
15500201-1	2004	Coumarins (pyranobenzopyran derivatives) (coumarin: CAS 91-64-5), organic compounds of known chemotherapeutic importance against bacteria, infectious diseases and tumors, were tested for their immunomodulatory effects.	Coumarins	0-9	breast cancer anti-estrogen resistance 1	Mus musculus	52-55
12420755-0	2002	Some coumarins and triphenylethene derivatives as inhibitors of human testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD type 3): further studies with tamoxifen on the rat testes microsomal enzyme.	Coumarins	5-14	hydroxysteroid 17-beta dehydrogenase 2	Homo sapiens	77-123
15199472-7	2003	The field of oral thrombin inhibitors is still dominated by the coumarins.	Coumarins	64-73	coagulation factor II, thrombin	Homo sapiens	18-26
12420755-0	2002	Some coumarins and triphenylethene derivatives as inhibitors of human testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD type 3): further studies with tamoxifen on the rat testes microsomal enzyme.	Coumarins	5-14	hydroxysteroid (17-beta) dehydrogenase 3	Rattus norvegicus	125-135
11543689-0	2001	Coumarins derivatives as dual inhibitors of acetylcholinesterase and monoamine oxidase.	Coumarins	0-9	acetylcholinesterase (Cartwright blood group)	Homo sapiens	44-64
11345694-1	2001	The influence of two plant coumarins, osthol and xanthotoxin, on intracellular Ca2+ ([Ca2+]i) transients evoked by TRH were studied in clonal rat pituitary GH4C1 cells.	Coumarins	27-36	thyrotropin releasing hormone	Rattus norvegicus	115-118
11408097-5	2001	However, exposure to coumarins during gestation increases the risk for MND in children of school age, odds ratio (OR) 1.9 (CI(95) 1.1-3.4), predominantly after exposure in the second or third trimester, odds ratio 2.1 (CI(95) 1.2-3.8).	Coumarins	21-30	olfactory receptor family 10 subfamily R member 3 pseudogene	Homo sapiens	102-121
9115691-12	1997	The coumarins 5-methoxypsoralen and 4,4"-di-O-methyl scandenin are poor cAK inhibitors (IC50 values 240 and 248 microM, respectively).	Coumarins	4-13	cyclin-dependent kinase 7	Rattus norvegicus	72-75
11215377-8	2000	In the future, such orally active direct inhibitors of thrombin and factor Xa, if they can be given safely without the need for laboratory monitoring, may replace the coumarins for the long-term treatment of thromboembolic disorders.	Coumarins	167-176	coagulation factor II, thrombin	Homo sapiens	55-63
10890030-10	2000	Using 10 coumarin-related compounds, we found that only those coumarins having a 7-alkyloxyl group induced GST, but not cytochrome P-450, activity.	Coumarins	62-71	hematopoietic prostaglandin D synthase	Mus musculus	107-110
10497143-7	1999	The catalytic activity of stably expressed UGT1A8 toward catechol estrogens, coumarins, flavonoids, anthraquinones, and phenolic compounds was much higher than that of UGT1A10.	Coumarins	77-86	UDP glucuronosyltransferase family 1 member A8	Homo sapiens	43-49
10497143-7	1999	The catalytic activity of stably expressed UGT1A8 toward catechol estrogens, coumarins, flavonoids, anthraquinones, and phenolic compounds was much higher than that of UGT1A10.	Coumarins	77-86	UDP glucuronosyltransferase family 1 member A10	Homo sapiens	168-175
11165023-2	2001	In our study we tested the influence of environmental hormones, such as phytoestrogens (flavonoids, coumarins, coumestans), on reductive and oxidative 17beta-HSD activity of the human 17beta-hydroxysteroid dehydrogenase type 5 (17beta-HSD 5).	Coumarins	100-109	RNA, U1 small nuclear 4	Homo sapiens	184-240
10655441-7	2000	RESULTS: Hsp90 binding to immobilized novobiocin was competed by soluble coumarins and ATP but not by geldanamycin or radicicol.	Coumarins	73-82	heat shock protein, 2	Mus musculus	9-14
10655441-9	2000	All three coumarins markedly reduced cellular levels of p185(erbB2), p60(v-src), Raf-1, and mutated p53.	Coumarins	10-19	cullin 7	Mus musculus	56-60
10655441-9	2000	All three coumarins markedly reduced cellular levels of p185(erbB2), p60(v-src), Raf-1, and mutated p53.	Coumarins	10-19	erb-b2 receptor tyrosine kinase 2	Mus musculus	61-66
10655441-9	2000	All three coumarins markedly reduced cellular levels of p185(erbB2), p60(v-src), Raf-1, and mutated p53.	Coumarins	10-19	plasma protein 1	Mus musculus	69-78
10655441-9	2000	All three coumarins markedly reduced cellular levels of p185(erbB2), p60(v-src), Raf-1, and mutated p53.	Coumarins	10-19	v-raf-leukemia viral oncogene 1	Mus musculus	81-86
10655441-9	2000	All three coumarins markedly reduced cellular levels of p185(erbB2), p60(v-src), Raf-1, and mutated p53.	Coumarins	10-19	transformation related protein 53, pseudogene	Mus musculus	100-103
10522711-3	1999	The similar DNA gyrase inhibitory activity of the novel class of coumarins to that of novobiocin demonstrates that L-rhamnose can effectively replace L-noviose.	Coumarins	65-74	DNA topoisomerase II alpha	Homo sapiens	12-22
10026280-0	1999	Probing the binding of coumarins and cyclothialidines to DNA gyrase.	Coumarins	23-32	DNA topoisomerase II alpha	Homo sapiens	57-67
10026280-1	1999	DNA gyrase is the target of a number of antibacterial agents, including the coumarins and the cyclothialidines.	Coumarins	76-85	DNA topoisomerase II alpha	Homo sapiens	0-10
9705221-4	1998	Transiently expressed human UGT1A8 shows glucuronidation activities with coumarins, anthraquinones, flavonoids, phenolic compounds, catechol estrogens, 17-hydroxyandrogens, primary amines such as the carcinogen 4-aminobiphenyl, and certain opioids.	Coumarins	73-82	UDP glucuronosyltransferase family 1 member A8	Homo sapiens	28-34
9616184-7	1998	In addition to amines, expressed human UGT1A3 catalyzed the glucuronidation of opioids (e.g. morphine and buprenorphine), coumarins, flavonoids (e.g. naringenin and quercetin), anthraquinones, and small phenolic compounds (e.g. 4-nitrophenol).	Coumarins	122-131	UDP glucuronosyltransferase family 1 member A3	Homo sapiens	39-45
9374426-5	1997	Analysis of structure-activity relationships showed certain chemical structures to be important for the inhibition of GSH-RD: (a) C-5 and C-7 hydroxylations in the A-ring, a carbonyl group at C-4, and the B-ring attached to C-2 in flavonoids; (b) C-2" and C-4" hydroxylations in chalcones; and (c) C-6 and C-7 hydroxylations in coumarins.	Coumarins	328-337	complement C7	Homo sapiens	138-141
9054609-1	1997	Several naturally occurring coumarins to which humans are routinely exposed have been previously found to be potent inhibitors and inactivators of cytochrome P450 (P450) 1A1-mediated monooxygenase in both murine hepatic microsomes and in a reconstituted system using purified human P450 1A1 [Cai et al.	Coumarins	28-37	cytochrome P450 family 4 subfamily F member 3	Homo sapiens	147-173
8536426-2	1995	The high probability of interactions can be explained by two pharmacokinetic properties of coumarins: high binding to plasma albumin (99%), being displaced by other drugs with greater affinity to this protein, and metabolism by liver microsomal enzymes (cytochrome P450), which can be induced or inhibited by other compounds (Shinn & Shrewsbury 1985).	Coumarins	91-100	cytochrome P450 family 4 subfamily F member 3	Homo sapiens	254-269
8853310-21	1996	These coumarins also inhibit the proinflammatory 5-lipoxygenase enzyme at micromolar concentrations.	Coumarins	6-15	arachidonate 5-lipoxygenase	Homo sapiens	49-63
8664301-3	1996	Supercoiling assays with intact DNA gyrase and ATPase assays with a 43-kDa N-terminal fragment of the B protein suggest that the drugs bind tightly, with Kd values <10(-7) M. In addition, the ATPase data suggest that 1 coumermycin molecule interacts with 2 molecules of the 43-kDa protein while the other coumarins form a 1:1 complex.	Coumarins	308-317	dynein axonemal heavy chain 8	Homo sapiens	47-53
8664301-3	1996	Supercoiling assays with intact DNA gyrase and ATPase assays with a 43-kDa N-terminal fragment of the B protein suggest that the drugs bind tightly, with Kd values <10(-7) M. In addition, the ATPase data suggest that 1 coumermycin molecule interacts with 2 molecules of the 43-kDa protein while the other coumarins form a 1:1 complex.	Coumarins	308-317	dynein axonemal heavy chain 8	Homo sapiens	195-201
7606814-0	1995	Binding of coumarins to site I of human serum albumin.	Coumarins	11-20	albumin	Homo sapiens	40-53
8806713-7	1996	It was found that both rat and human UGT1.1 exhibited comparable substrate specificities and efficiencies (Vmax/Km) of glucuronide formation for anthraquinones, coumarins, estrogens, flavonoids, and phenolic compounds.	Coumarins	161-170	UDP glucuronosyltransferase family 1 member A1	Homo sapiens	37-43
8068031-5	1994	The other four coumarins (all containing ortho-dihydroxy catechol functions, and found previously to be pro-oxidant in cell-free systems by virtue of reduction of ferric to ferrous ions), themselves rapidly reduced cytochrome c.	Coumarins	15-24	cytochrome c, somatic	Homo sapiens	215-227
7742536-4	1995	Based on a single measurement, there were 22 (4.6%) patients with a PC deficiency (PC activity, less than 0.67 U/mL or PC antigen, less than 0.33 U/mL when using coumarins).	Coumarins	162-171	protein C, inactivator of coagulation factors Va and VIIIa	Homo sapiens	68-70
8046621-1	1994	UDP-glucuronosyltransferase (UGT) activities have been described as heterogeneous, i.e. supported by a family of isoenzymes, each of them being capable of conjugating a given chemical family of aglycons, including steroids, coumarines, and phenols.	Coumarins	224-234	UDP glucuronosyltransferase family 1 member A complex locus	Homo sapiens	0-27
7847183-7	1994	Similar effects of the active coumarins were obtained using arachidonic acid as substrate for rat leukocyte eicosanoid generation, confirming that they act at the 5-lipoxygenase/cyclooxygenase level.	Coumarins	30-39	arachidonate 5-lipoxygenase	Rattus norvegicus	163-177
7847183-8	1994	The same profile of activity was also shown when the coumarins were tested against 5-lipoxygenase in human polymorphonuclear neutrophils.	Coumarins	53-62	arachidonate 5-lipoxygenase	Homo sapiens	83-97
8046621-1	1994	UDP-glucuronosyltransferase (UGT) activities have been described as heterogeneous, i.e. supported by a family of isoenzymes, each of them being capable of conjugating a given chemical family of aglycons, including steroids, coumarines, and phenols.	Coumarins	224-234	UDP glucuronosyltransferase family 1 member A complex locus	Homo sapiens	29-32
8117927-7	1993	Furthermore, experiments using a two-stage incubation assay revealed that coriandrin, imperatorin, ostruthin, and several other natural coumarins inactivated hepatic EROD activity (i.e., predominantly cytochrome P450 1A1-mediated) and that isopimpinellin inactivated hepatic PROD activity (i.e., predominantly cytochrome P450 2B1-mediated).	Coumarins	136-145	cytochrome P450, family 1, subfamily a, polypeptide 1	Mus musculus	201-220
2025958-4	1991	The coumarins were able to potentiate human MNC IL-1 beta production by lipopolysaccharide (LPS) in a dose-dependent manner.	Coumarins	4-13	interleukin 1 beta	Homo sapiens	48-57
1322662-8	1992	Several other coumarins with one or more hydroxyl substituents were also capable of effectively removing superoxide anions (IC50 3.7-72 microM), although some could not be quantified due to direct rapid reduction of cytochrome c.	Coumarins	14-23	cytochrome c, somatic	Homo sapiens	216-228
2071271-1	1991	The interaction between free fatty acids and urapidil binding to human serum albumin (HSA) was investigated, whereby the binding properties at the coumarine binding site were influenced by the HSA fatty acid content.	Coumarins	147-156	albumin	Homo sapiens	71-84
34961392-6	2021	The interactions of CXCL12 and LEP with coumarins were studied by molecular docking and it shows good interaction as well as docking score as compared to the standard one.	Coumarins	40-49	C-X-C motif chemokine ligand 12	Homo sapiens	20-26
2183798-2	1990	5-Lipoxygenase and alpha-D-glucosidase inhibitory activities of coumarins greatly increased through 3-hydroxylation.	Coumarins	64-73	arachidonate 5-lipoxygenase	Homo sapiens	0-14
7835232-6	1994	UGT2B15 stably expressed in HK293 cells displayed glucuronidation activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites.	Coumarins	176-185	UDP glucuronosyltransferase family 2 member B15	Homo sapiens	0-7
34961392-6	2021	The interactions of CXCL12 and LEP with coumarins were studied by molecular docking and it shows good interaction as well as docking score as compared to the standard one.	Coumarins	40-49	leptin	Homo sapiens	31-34
34069658-0	2021	Antiplatelet Activity of Coumarins: In Vitro Assays on COX-1.	Coumarins	25-34	mitochondrially encoded cytochrome c oxidase I	Homo sapiens	55-60
34982427-8	2021	The PI3K/Akt signal pathway appears to be central to the anti-tumor activity of the coumarins analyzed in this review.	Coumarins	84-93	AKT serine/threonine kinase 1	Homo sapiens	9-12
33602041-4	2021	These data further corroborate our previous findings on analogous derivatives, confirming that both coumarins and psoralens are interesting scaffolds for the design of isozyme selective hCA inhibitors.	Coumarins	100-109	HCA1	Homo sapiens	186-189
34858164-4	2021	It is showed that some natural compounds such as flavonoids, phenols, glycosides and coumarins have a protective role in melanocytes and thereby arrest the depigmentation, and, additionally, Nrf2/HO-1, MAPK, JAK/STAT, cAMP/PKA, and Wnt/beta-catenin signaling pathways were reported to be implicated in these protective effects.	Coumarins	85-94	heme oxygenase 1	Homo sapiens	196-200
34858164-4	2021	It is showed that some natural compounds such as flavonoids, phenols, glycosides and coumarins have a protective role in melanocytes and thereby arrest the depigmentation, and, additionally, Nrf2/HO-1, MAPK, JAK/STAT, cAMP/PKA, and Wnt/beta-catenin signaling pathways were reported to be implicated in these protective effects.	Coumarins	85-94	cathelicidin antimicrobial peptide	Homo sapiens	218-222
34858164-4	2021	It is showed that some natural compounds such as flavonoids, phenols, glycosides and coumarins have a protective role in melanocytes and thereby arrest the depigmentation, and, additionally, Nrf2/HO-1, MAPK, JAK/STAT, cAMP/PKA, and Wnt/beta-catenin signaling pathways were reported to be implicated in these protective effects.	Coumarins	85-94	catenin beta 1	Homo sapiens	236-248
34641543-5	2021	The 3"-fluoro-substituted coumarins 3e and 4e, along with 3-(4-acetyloxyphenyl)-6,8-dibromo-4-methyl-chromen-2-one (3k), were the most potent lipoxygenase (LOX) inhibitors (IC50 11.4, 4.1, and 8.7 muM, respectively) while displaying remarkable hydroxyl radical scavenging ability, 85.2%, 100%, and 92.9%, respectively.	Coumarins	26-35	linoleate 9S-lipoxygenase-4	Glycine max	142-154
34505513-4	2021	When the fluorescent agent, coumarine, was conjugated to TEPP-46, the bioprobe TEPC466 showed a high degree of selectivity and sensitivity for the detection of PKM2 protein via the AIE effect.	Coumarins	28-37	pyruvate kinase M1/2	Homo sapiens	160-164
34833955-6	2021	In this study, a series of phytobioactives were screened based on their chemical classes such as coumarins, flavonoids, and triterpenoids for their action on NQO1.	Coumarins	97-106	NAD(P)H quinone dehydrogenase 1	Homo sapiens	158-162
34169921-1	2021	Two known coumarins, scopoletin (SP) and umbelliferone (UB), were isolated from Cortex Mori (CM).	Coumarins	10-19	trefoil factor 2	Rattus norvegicus	21-31
34169921-1	2021	Two known coumarins, scopoletin (SP) and umbelliferone (UB), were isolated from Cortex Mori (CM).	Coumarins	10-19	trefoil factor 2	Rattus norvegicus	33-35
35616541-4	2022	EXPERT OPINION: The available 3D crystal structures of hCA IX, XII as well as the off target isoforms hCA I and II, afforded structure-based drug design opportunities, which led to the development of various isoform-selective small molecule inhibitors belonging to diverse classes (sulfonamides, sulfamates, benzoxaboroles, selenols, coumarins, sulfocoumarins and isocoumarins).	Coumarins	334-343	carbonic anhydrase 9	Homo sapiens	55-61
35616541-4	2022	EXPERT OPINION: The available 3D crystal structures of hCA IX, XII as well as the off target isoforms hCA I and II, afforded structure-based drug design opportunities, which led to the development of various isoform-selective small molecule inhibitors belonging to diverse classes (sulfonamides, sulfamates, benzoxaboroles, selenols, coumarins, sulfocoumarins and isocoumarins).	Coumarins	334-343	HCA1	Homo sapiens	102-105
901810-1	1977	Prothrombin has been purified from the plasmas of normal human donors and from patients ingesting coumarins.	Coumarins	98-107	coagulation factor II, thrombin	Homo sapiens	0-11
35168478-3	2022	A recent study has shown that coumarins tend to be more selective towards MAO-B than MAO-A when connected to a hex-5-ynyloxy chain at position 6 in contrast to their C7-isomers.	Coumarins	30-39	monoamine oxidase B	Homo sapiens	74-79
35168478-3	2022	A recent study has shown that coumarins tend to be more selective towards MAO-B than MAO-A when connected to a hex-5-ynyloxy chain at position 6 in contrast to their C7-isomers.	Coumarins	30-39	monoamine oxidase A	Homo sapiens	85-90
3922420-1	1985	The effects of various coumarins (i.e. esculetin, daphnetin and fraxetin) on the formation of the 5-lipoxygenase product, 5-HETE, and the cyclooxygenase product, HHT, were studied.	Coumarins	23-32	arachidonate 5-lipoxygenase	Homo sapiens	98-112
6740566-0	1984	Antithrombin III in patients with acute deep vein thrombosis during heparin treatment (subcutaneous and intravenous) and during and after treatment with oral coumarins.	Coumarins	158-167	serpin family C member 1	Homo sapiens	0-16
6659943-0	1983	[Quantitative TLC-densitometry of coumarins in Qin Pi (Fraxinus stylosa)].	Coumarins	34-43	forkhead box G1	Homo sapiens	47-50
35249659-19	2022	Our results suggest that co-expression (or addition) of CYB5 with CYP6P9 variants, recombinantly expressed in insect cells, can significantly enhance their metabolic capacity to oxidize coumarins, but not deltamethrin.	Coumarins	186-195	cytochrome b5 type A	Homo sapiens	56-60
3086557-0	1986	Synthesis and rat lens aldose reductase inhibitory activity of some benzopyran-2-ones.	Coumarins	68-85	aldo-keto reductase family 1 member B1	Rattus norvegicus	23-39
3925953-4	1985	In Wistar rats, we found that some coumarins were poor substrates of UDPGT (GT1) and that twenty monoterpenoid alcohol activities showed typical phenobarbital-inducible behavior.	Coumarins	35-44	beta-1,3-glucuronyltransferase 2	Rattus norvegicus	69-74
169352-2	1975	Synthesis and antifertility and estrogen receptor binding activities of coumarins and delta3-isoflavenes.	Coumarins	72-81	estrogen receptor 1 (alpha)	Mus musculus	32-49
869690-0	1977	Carbon-13 NMR spectra of some C-3 prenylated coumarins from Rutaceae (author"s transl).	Coumarins	45-54	complement C3	Homo sapiens	30-33
125199-3	1975	Some of the coumarins stimulated ATPase activity, but all of them inhibited uncoupler-stimulated ATPase activity.	Coumarins	12-21	dynein axonemal heavy chain 8	Homo sapiens	33-39
125199-3	1975	Some of the coumarins stimulated ATPase activity, but all of them inhibited uncoupler-stimulated ATPase activity.	Coumarins	12-21	dynein axonemal heavy chain 8	Homo sapiens	97-103
125199-4	1975	Coumarins with free or substituted phenolic groups were found to exert profound effects on respiration and ATPase activity.	Coumarins	0-9	dynein axonemal heavy chain 8	Homo sapiens	107-113
33830755-2	2021	These novel polarized coumarins, possessing a beta-ketoester moiety, have been employed to synthesize more rigid and helical coumarin-pyrazolones, which display green fluorescence.	Coumarins	22-31	amyloid beta precursor protein	Homo sapiens	44-50
33492969-0	2021	Visible-Light-Induced Direct Csp2-H Radical Trifluoroethylation of Coumarins with 1,1,1-Trifluoro-2-iodoethane (CF3CH2I).	Coumarins	67-76	regulator of calcineurin 2	Homo sapiens	29-33
33563156-3	2022	METHOD: In this work two home-made databases from synthetic quinolines and coumarins were virtually docked against viral proteases (3CL and PL), human cell surface proteases (TMPRSS2 and furin) and spike proteins (S1 and S2).	Coumarins	75-84	transmembrane serine protease 2	Homo sapiens	175-182
33563156-3	2022	METHOD: In this work two home-made databases from synthetic quinolines and coumarins were virtually docked against viral proteases (3CL and PL), human cell surface proteases (TMPRSS2 and furin) and spike proteins (S1 and S2).	Coumarins	75-84	furin, paired basic amino acid cleaving enzyme	Homo sapiens	187-192
33866633-7	2021	Moreover, glycosylation activity of UGT73C7 resulted in the redirection of phenylpropanoid metabolic flux to biosynthesis of hydroxycinnamic acids and coumarins.	Coumarins	151-160	UDP-glucosyl transferase 73C7	Arabidopsis thaliana	36-43
33672051-0	2021	Insulin-Mimetic Dihydroxanthyletin-Type Coumarins from Angelica decursiva with Protein Tyrosine Phosphatase 1B and alpha-Glucosidase Inhibitory Activities and Docking Studies of Their Molecular Mechanisms.	Coumarins	40-49	insulin	Homo sapiens	0-7
33672051-2	2021	The goal of this study was to evaluate the potential of four natural major dihydroxanthyletin-type coumarins-(+)-trans-decursidinol, Pd-C-I, Pd-C-II, and Pd-C-III-to inhibit the enzymes, protein tyrosine phosphatase 1B (PTP1B) and alpha-glucosidase.	Coumarins	99-108	protein tyrosine phosphatase non-receptor type 1	Homo sapiens	220-225
33672051-5	2021	Docking simulations of these coumarins showed negative binding energies and a similar proximity to residues in the PTP1B and alpha-glucosidase binding pocket, which means they are closely connected and strongly binding with the active enzyme site.	Coumarins	29-38	protein tyrosine phosphatase non-receptor type 1	Homo sapiens	115-120
33672051-6	2021	In addition, dihydroxanthyletin-type coumarins are up to 40 microM non-toxic in HepG2 cells and have substantially increased glucose uptake and decreased expression of PTP1B in insulin-resistant HepG2 cells.	Coumarins	37-46	protein tyrosine phosphatase non-receptor type 1	Homo sapiens	168-173
33672051-6	2021	In addition, dihydroxanthyletin-type coumarins are up to 40 microM non-toxic in HepG2 cells and have substantially increased glucose uptake and decreased expression of PTP1B in insulin-resistant HepG2 cells.	Coumarins	37-46	insulin	Homo sapiens	177-184
33672051-8	2021	Our overall findings showed that dihydroxanthyletin-type coumarins derived from A. decursiva is used as a dual inhibitor for enzymes, such as PTP1B and alpha-glucosidase, as well as for insulin susceptibility.	Coumarins	57-66	protein tyrosine phosphatase non-receptor type 1	Homo sapiens	142-147
33672051-8	2021	Our overall findings showed that dihydroxanthyletin-type coumarins derived from A. decursiva is used as a dual inhibitor for enzymes, such as PTP1B and alpha-glucosidase, as well as for insulin susceptibility.	Coumarins	57-66	insulin	Homo sapiens	186-193
33579030-8	2021	A statistically significant decrease in the level of tumor necrosis factor alpha and cyclooxygenase-II in lipopolysaccharide-treated rodents after coumarins" administration was observed.	Coumarins	147-156	tumor necrosis factor	Mus musculus	53-80
33556550-0	2021	Bone anti-resorptive effects of coumarins on RANKL downstream cellular signaling: A systematic review of the literature.	Coumarins	32-41	TNF superfamily member 11	Homo sapiens	45-50
33556550-7	2021	RESULTS: Coumarins have been reported to downregulate RANKL-RANK signaling and various downstream signaling pathways required for osteoclast development, such as NF-kappaB, MAPK, Akt, and Ca2+ signaling, as well as pathways downstream of the nuclear factor of activated T-cells (NFATc1), including tartrate-resistant acid phosphatase (TRAP), cathepsin K (CTSK), and matrix metalloproteinase 9 (MMP-9).	Coumarins	9-18	TNF superfamily member 11	Homo sapiens	54-59
33556550-7	2021	RESULTS: Coumarins have been reported to downregulate RANKL-RANK signaling and various downstream signaling pathways required for osteoclast development, such as NF-kappaB, MAPK, Akt, and Ca2+ signaling, as well as pathways downstream of the nuclear factor of activated T-cells (NFATc1), including tartrate-resistant acid phosphatase (TRAP), cathepsin K (CTSK), and matrix metalloproteinase 9 (MMP-9).	Coumarins	9-18	AKT serine/threonine kinase 1	Homo sapiens	179-182
33556550-7	2021	RESULTS: Coumarins have been reported to downregulate RANKL-RANK signaling and various downstream signaling pathways required for osteoclast development, such as NF-kappaB, MAPK, Akt, and Ca2+ signaling, as well as pathways downstream of the nuclear factor of activated T-cells (NFATc1), including tartrate-resistant acid phosphatase (TRAP), cathepsin K (CTSK), and matrix metalloproteinase 9 (MMP-9).	Coumarins	9-18	nuclear factor of activated T cells 1	Homo sapiens	279-285
33556550-7	2021	RESULTS: Coumarins have been reported to downregulate RANKL-RANK signaling and various downstream signaling pathways required for osteoclast development, such as NF-kappaB, MAPK, Akt, and Ca2+ signaling, as well as pathways downstream of the nuclear factor of activated T-cells (NFATc1), including tartrate-resistant acid phosphatase (TRAP), cathepsin K (CTSK), and matrix metalloproteinase 9 (MMP-9).	Coumarins	9-18	cathepsin K	Homo sapiens	342-353
33556550-7	2021	RESULTS: Coumarins have been reported to downregulate RANKL-RANK signaling and various downstream signaling pathways required for osteoclast development, such as NF-kappaB, MAPK, Akt, and Ca2+ signaling, as well as pathways downstream of the nuclear factor of activated T-cells (NFATc1), including tartrate-resistant acid phosphatase (TRAP), cathepsin K (CTSK), and matrix metalloproteinase 9 (MMP-9).	Coumarins	9-18	cathepsin K	Homo sapiens	355-359
33556550-7	2021	RESULTS: Coumarins have been reported to downregulate RANKL-RANK signaling and various downstream signaling pathways required for osteoclast development, such as NF-kappaB, MAPK, Akt, and Ca2+ signaling, as well as pathways downstream of the nuclear factor of activated T-cells (NFATc1), including tartrate-resistant acid phosphatase (TRAP), cathepsin K (CTSK), and matrix metalloproteinase 9 (MMP-9).	Coumarins	9-18	matrix metallopeptidase 9	Homo sapiens	366-392
33556550-7	2021	RESULTS: Coumarins have been reported to downregulate RANKL-RANK signaling and various downstream signaling pathways required for osteoclast development, such as NF-kappaB, MAPK, Akt, and Ca2+ signaling, as well as pathways downstream of the nuclear factor of activated T-cells (NFATc1), including tartrate-resistant acid phosphatase (TRAP), cathepsin K (CTSK), and matrix metalloproteinase 9 (MMP-9).	Coumarins	9-18	matrix metallopeptidase 9	Homo sapiens	394-399
33492969-1	2021	Herein, we developed the first visible-light-induced direct Csp2-H radical 2,2,2-trifluoroethylation of coumarins with commercially available and cheap reagent CF3CH2I at room temperature.	Coumarins	104-113	regulator of calcineurin 2	Homo sapiens	60-64
33218896-7	2021	Among all coumarins tested, 4-trifluoromethyl-6,7-dihydroxycoumarin (Cpd 4) displayed the most potent inhibitory activity towards Mcl-1 (Ki = 0.21 +- 0.02 muM, IC50 = 1.21 +- 0.56 muM, respectively), for which the beneficial effect on taxol resistance was also validated in A549 cells.	Coumarins	10-19	inositol polyphosphate-5-phosphatase E	Homo sapiens	69-74
33205512-8	2021	It also highlighted that under Fe deficiency conditions, coumarins transport from the cortex to the rhizosphere relies on the PDR9 transporter.	Coumarins	57-66	pleiotropic drug resistance 9	Arabidopsis thaliana	126-130
33038795-8	2021	Concerning non-sulfonamide coumarin derivatives, coumarins 8 exhibited excellent activity and selectivity profiles against the target hCA IX/XII, whereas, coumarins 11 and 12 reported excellent selectivity profile, but they barely inhibited hCA IX/XII with KIs spanning in the micromolar ranges.	Coumarins	49-58	carbonic anhydrase 9	Homo sapiens	134-144
33396516-10	2020	To sum up, modification mimicking natural occurring coumarins shed light on CAR studies and the established screening system provides a rapid method for the discovery and development of CAR activators.	Coumarins	52-61	nuclear receptor subfamily 1, group I, member 3	Mus musculus	76-79
33396516-10	2020	To sum up, modification mimicking natural occurring coumarins shed light on CAR studies and the established screening system provides a rapid method for the discovery and development of CAR activators.	Coumarins	52-61	nuclear receptor subfamily 1, group I, member 3	Mus musculus	186-189
32637779-0	2020	In Silico Studies and In Vivo MAOA Inhibitory Activity of Coumarins Isolated from Angelica archangelica Extract: An Approach toward Antidepressant Activity.	Coumarins	58-67	monoamine oxidase A	Mus musculus	30-34
33344242-3	2020	In particular, coumarins have very significant anti-tumor abilities and a variety of anti-tumor mechanisms, including inhibition of carbonic anhydrase, targeting PI3K/Akt/mTOR signaling pathways, inducing cell apoptosis protein activation, inhibition of tumor multidrug resistance, inhibition of microtubule polymerization, regulating the reactive oxygen species, and inhibition of tumor angiogenesis, etc.	Coumarins	15-24	AKT serine/threonine kinase 1	Homo sapiens	167-170
33344242-3	2020	In particular, coumarins have very significant anti-tumor abilities and a variety of anti-tumor mechanisms, including inhibition of carbonic anhydrase, targeting PI3K/Akt/mTOR signaling pathways, inducing cell apoptosis protein activation, inhibition of tumor multidrug resistance, inhibition of microtubule polymerization, regulating the reactive oxygen species, and inhibition of tumor angiogenesis, etc.	Coumarins	15-24	mechanistic target of rapamycin kinase	Homo sapiens	171-175
32991865-0	2020	Synergistic transport of a fluorescent coumarin probe marks coumarins as pharmacological modulators of Organic anion-transporting polypeptide, OATP3A1.	Coumarins	60-69	solute carrier organic anion transporter family member 3A1	Homo sapiens	143-150
32991865-9	2020	Moreover, coumarins are good candidates for OATP3A1-targeted drug delivery and as pharmacological modulators of OATP3A1.	Coumarins	10-19	solute carrier organic anion transporter family member 3A1	Homo sapiens	44-51
32991865-9	2020	Moreover, coumarins are good candidates for OATP3A1-targeted drug delivery and as pharmacological modulators of OATP3A1.	Coumarins	10-19	solute carrier organic anion transporter family member 3A1	Homo sapiens	112-119
32816867-7	2020	P-gp modulatory effects have been previously demonstrated using selected TCM, including the flavonoids, alkaloids, terpenoids, coumarins, and quinonoids compounds, and some Chinese medicine extracts.	Coumarins	127-136	ATP binding cassette subfamily B member 1	Homo sapiens	0-4
32250498-8	2020	These coumarins also modulated neuronal cell death by reducing the level of proinflammatory cytokines (tumour necrosis factor-alpha and interleukin-6), inhibiting the overexpression of inflammatory markers (nuclear factor kappaB [NF-kappaB] and cyclooxygenase II), and upregulating the expression of NF-kappaB inhibitor (IkappaB-alpha).	Coumarins	6-15	interleukin 6	Rattus norvegicus	136-149
32250498-8	2020	These coumarins also modulated neuronal cell death by reducing the level of proinflammatory cytokines (tumour necrosis factor-alpha and interleukin-6), inhibiting the overexpression of inflammatory markers (nuclear factor kappaB [NF-kappaB] and cyclooxygenase II), and upregulating the expression of NF-kappaB inhibitor (IkappaB-alpha).	Coumarins	6-15	NFKB inhibitor alpha	Rattus norvegicus	321-334
30979692-14	2020	Secondary metabolites with a high BDNF expression belonged to flavonoids, xanthone, coumarines, tannin, naphtalenes, terpenoids and carotenoid skeleton.	Coumarins	84-94	brain derived neurotrophic factor	Homo sapiens	34-38
32664320-7	2020	Our DFT computational studies on the three natural products of the same coumarin family docked into the active site of CYP3A4 (PDB 4D78) show different behavior for these coumarins at the active site.	Coumarins	171-180	cytochrome P450 family 3 subfamily A member 4	Homo sapiens	119-125
32598267-5	2021	METHOD: C-4 substituted coumarins analogues (1-10) have been synthesized using conventional heating and microwave irradiation.	Coumarins	24-33	complement C4A (Rodgers blood group)	Homo sapiens	8-11
32637779-1	2020	The current investigation was aimed at in vivo MAOA inhibitory activity of coumarins angelicin, bergapten, and scopoletin isolated from the roots of Angelica archangelica.	Coumarins	75-84	monoamine oxidase A	Mus musculus	47-51
31542715-3	2019	Inhibition of CA IX activity by small molecule CA inhibitors like sulfonamides, sulfonamide derivative or coumarins leads to inhibition of tumorigenesis.	Coumarins	106-115	carbonic anhydrase 9	Homo sapiens	14-19
32370238-4	2020	Moreover, in order to understand the mechanism, the binding interactions between coumarins and their targets: (i) AChE and (ii) Abeta1-42 peptide were investigated in silico.	Coumarins	81-90	acetylcholinesterase (Cartwright blood group)	Homo sapiens	114-118
32370238-5	2020	All coumarins exhibited mild to moderate AChE and self-induced Abeta aggregation inhibitory actions.	Coumarins	4-13	acetylcholinesterase (Cartwright blood group)	Homo sapiens	41-45
32370238-6	2020	In addition, the coumarins substituted with the long alkyl chain at position 6 or 8 illustrated ability to inhibit AChE-induced Abeta aggregation, resulting from their dual binding site at catalytic anionic site and peripheral active site in AChE.	Coumarins	17-26	acetylcholinesterase (Cartwright blood group)	Homo sapiens	115-119
32370238-6	2020	In addition, the coumarins substituted with the long alkyl chain at position 6 or 8 illustrated ability to inhibit AChE-induced Abeta aggregation, resulting from their dual binding site at catalytic anionic site and peripheral active site in AChE.	Coumarins	17-26	acetylcholinesterase (Cartwright blood group)	Homo sapiens	242-246
32377290-0	2020	Coumarins as Modulators of the Keap1/Nrf2/ARE Signaling Pathway.	Coumarins	0-9	kelch like ECH associated protein 1	Homo sapiens	31-36
32377290-0	2020	Coumarins as Modulators of the Keap1/Nrf2/ARE Signaling Pathway.	Coumarins	0-9	NFE2 like bZIP transcription factor 2	Homo sapiens	37-41
32377290-7	2020	Some coumarins have shown an ability to activate Nrf2 signaling in different cells and animal models.	Coumarins	5-14	NFE2 like bZIP transcription factor 2	Homo sapiens	49-53
32377290-9	2020	Additionally, molecular docking simulations were utilized to investigate the potential binding mode of these coumarins with Keap1 as a strategy to disrupt Keap1/Nrf2 protein-protein interaction and activate Nrf2 signaling.	Coumarins	109-118	kelch like ECH associated protein 1	Homo sapiens	124-129
32377290-9	2020	Additionally, molecular docking simulations were utilized to investigate the potential binding mode of these coumarins with Keap1 as a strategy to disrupt Keap1/Nrf2 protein-protein interaction and activate Nrf2 signaling.	Coumarins	109-118	kelch like ECH associated protein 1	Homo sapiens	155-160
32377290-9	2020	Additionally, molecular docking simulations were utilized to investigate the potential binding mode of these coumarins with Keap1 as a strategy to disrupt Keap1/Nrf2 protein-protein interaction and activate Nrf2 signaling.	Coumarins	109-118	NFE2 like bZIP transcription factor 2	Homo sapiens	161-165
32377290-9	2020	Additionally, molecular docking simulations were utilized to investigate the potential binding mode of these coumarins with Keap1 as a strategy to disrupt Keap1/Nrf2 protein-protein interaction and activate Nrf2 signaling.	Coumarins	109-118	NFE2 like bZIP transcription factor 2	Homo sapiens	207-211
31489680-10	2019	Qualitative characterisation of APM indicated existence of alkaloids, terpenoids, coumarins, cardiac glycosides, phenols, flavonoids, saponins, tannins and sterols.	Coumarins	82-91	alanyl aminopeptidase, membrane	Rattus norvegicus	32-35
31298543-0	2019	Traceless-Activation Strategy for Rh-Catalyzed Csp2-H Arylation of Coumarins.	Coumarins	67-76	regulator of calcineurin 2	Homo sapiens	47-51
30354155-0	2018	Visible-Light- and Oxygen-Promoted Direct Csp2-H Radical Difluoromethylation of Coumarins and Antifungal Activities.	Coumarins	80-89	regulator of calcineurin 2	Homo sapiens	42-46
31340484-9	2019	It was found that the production of NO and MCP-1 was obviously inhibited by three coumarins.	Coumarins	82-91	mast cell protease 1	Mus musculus	43-48
30637618-0	2019	Correction to: Dihydroxanthyletin-type coumarins from Angelica decursiva that inhibits the formation of advanced glycation end products and human recombinant aldose reductase.	Coumarins	39-48	aldo-keto reductase family 1 member B	Homo sapiens	158-174
30931006-2	2019	Diversely substituted indoles (Ar1) react with quinoline aldehydes, quinolone aldehydes, chromone aldehydes, and fluorene aldehydes (Ar2CHO) and coumarins (Ar3) in 1:1:1 ratio to form the corresponding tris(heteroaryl)methanes (Ar1Ar2Ar3)CH along with (Ar1Ar1Ar2)CH triads.	Coumarins	145-154	transcription factor 20	Homo sapiens	31-34
30733181-0	2019	Coumarins ameliorate diabetogenic action of dexamethasone via Akt activation and AMPK signaling in skeletal muscle.	Coumarins	0-9	thymoma viral proto-oncogene 1	Mus musculus	62-65
30584780-0	2019	The Inhibition Kinetics and Potential Anti-Migration Activity of NQO1 Inhibitory Coumarins on Cholangiocarcinoma Cells.	Coumarins	81-90	NAD(P)H quinone dehydrogenase 1	Homo sapiens	65-69
30584780-5	2019	Among the different chemical classes of natural NQO1 inhibitors are coumarins, flavonoids, and triterpenoids.	Coumarins	68-77	NAD(P)H quinone dehydrogenase 1	Homo sapiens	48-52
30584780-6	2019	Coumarins are a group of particularly potent NQO1 inhibitors.	Coumarins	0-9	NAD(P)H quinone dehydrogenase 1	Homo sapiens	45-49
31163215-3	2019	All tested coumarins except a C4 phenyl derivative (11) showed higher inhibitory activities for CYP2A6 over the other CYP isoforms, including CYP1A2, CYP2D6, CYP2E1, CYP3A4, CYP2C8, and CYP2C9.	Coumarins	11-20	cytochrome P450 family 2 subfamily A member 6	Homo sapiens	96-102
31163215-3	2019	All tested coumarins except a C4 phenyl derivative (11) showed higher inhibitory activities for CYP2A6 over the other CYP isoforms, including CYP1A2, CYP2D6, CYP2E1, CYP3A4, CYP2C8, and CYP2C9.	Coumarins	11-20	cytochrome P450 family 1 subfamily A member 2	Homo sapiens	142-148
31163215-3	2019	All tested coumarins except a C4 phenyl derivative (11) showed higher inhibitory activities for CYP2A6 over the other CYP isoforms, including CYP1A2, CYP2D6, CYP2E1, CYP3A4, CYP2C8, and CYP2C9.	Coumarins	11-20	cytochrome P450 family 2 subfamily D member 6	Homo sapiens	150-156
31163215-3	2019	All tested coumarins except a C4 phenyl derivative (11) showed higher inhibitory activities for CYP2A6 over the other CYP isoforms, including CYP1A2, CYP2D6, CYP2E1, CYP3A4, CYP2C8, and CYP2C9.	Coumarins	11-20	cytochrome P450 family 2 subfamily E member 1	Homo sapiens	158-164
31163215-3	2019	All tested coumarins except a C4 phenyl derivative (11) showed higher inhibitory activities for CYP2A6 over the other CYP isoforms, including CYP1A2, CYP2D6, CYP2E1, CYP3A4, CYP2C8, and CYP2C9.	Coumarins	11-20	cytochrome P450 family 3 subfamily A member 4	Homo sapiens	166-172
31163215-3	2019	All tested coumarins except a C4 phenyl derivative (11) showed higher inhibitory activities for CYP2A6 over the other CYP isoforms, including CYP1A2, CYP2D6, CYP2E1, CYP3A4, CYP2C8, and CYP2C9.	Coumarins	11-20	cytochrome P450 family 2 subfamily C member 8	Homo sapiens	174-180
31163215-3	2019	All tested coumarins except a C4 phenyl derivative (11) showed higher inhibitory activities for CYP2A6 over the other CYP isoforms, including CYP1A2, CYP2D6, CYP2E1, CYP3A4, CYP2C8, and CYP2C9.	Coumarins	11-20	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	186-192
31163215-4	2019	Of these coumarins, 6,7-dihydroxycoumarin (1) and 7,8-dihydroxycoumarin (9) were found to be potent inhibitors of CYP2A6 with IC50/Ki value of 0.39/0.25 and 4.61/3.02 muM, respectively, compared to methoxalen as positive control (IC50/Ki = 0.43/0.26 muM).	Coumarins	9-18	cytochrome P450 family 2 subfamily A member 6	Homo sapiens	114-120
31163215-5	2019	In contrast, other coumarins showed low or decreased CYP2A6-inhibiting activities.	Coumarins	19-28	cytochrome P450 family 2 subfamily A member 6	Homo sapiens	53-59
31022888-3	2019	Coumarins, phytochemicals abundant in food and commonly used in fragrances and cosmetics, have been shown to interact with P450 enzymes as substrates and/or inhibitors.	Coumarins	0-9	cytochrome P450 family 2 subfamily B member 6	Homo sapiens	123-127
30526468-0	2019	DFT-Based QSAR Modelling of Inhibitory Activity of Coumarins and Sulfocoumarins on Carbonic Anhydrase (CA) Isoforms (CA I and CA II).	Coumarins	51-60	carbonic anhydrase 1	Homo sapiens	117-121
30526468-0	2019	DFT-Based QSAR Modelling of Inhibitory Activity of Coumarins and Sulfocoumarins on Carbonic Anhydrase (CA) Isoforms (CA I and CA II).	Coumarins	51-60	carbonic anhydrase 2	Homo sapiens	126-131
30457328-7	2018	According to the obtained results, only complexes 3-PF6 and 5-PF6, featuring coumarins as ancillary ligands and endowed with high redox stability in solution, display antiproliferative effects, with 5-PF6 being the most potent, while all of the others are scarcely active to nonactive in the selected cell lines.	Coumarins	77-86	sperm associated antigen 17	Homo sapiens	52-55
30457328-7	2018	According to the obtained results, only complexes 3-PF6 and 5-PF6, featuring coumarins as ancillary ligands and endowed with high redox stability in solution, display antiproliferative effects, with 5-PF6 being the most potent, while all of the others are scarcely active to nonactive in the selected cell lines.	Coumarins	77-86	sperm associated antigen 17	Homo sapiens	62-65
30457328-7	2018	According to the obtained results, only complexes 3-PF6 and 5-PF6, featuring coumarins as ancillary ligands and endowed with high redox stability in solution, display antiproliferative effects, with 5-PF6 being the most potent, while all of the others are scarcely active to nonactive in the selected cell lines.	Coumarins	77-86	sperm associated antigen 17	Homo sapiens	62-65
30354155-1	2018	An efficient general method using a clean and transition-metal-free photochemical strategy for the direct Csp2-H radical difluoromethylation of coumarins with HCF2SO2Na was developed.	Coumarins	144-153	regulator of calcineurin 2	Homo sapiens	106-110
29772410-1	2018	Coumarins and meroterpene from the fruits of Cullen corylifolium were evaluated for their ability to bind and activate human estrogen receptor alpha (hERalpha) by a combination of in vitro studies and molecular dynamics simulations.	Coumarins	0-9	estrogen receptor 1	Homo sapiens	125-148
30214075-3	2018	Here, we present a rational follow-up investigation of the interaction between ELAV isoform HuR and structurally-related compounds (i.e., flavonoids and coumarins), naturally decorated with different functional groups, by means of STD-NMR and Molecular Modelling.	Coumarins	153-162	ELAV like RNA binding protein 1	Homo sapiens	92-95
29893871-0	2018	The Nicotiana tabacum ABC transporter NtPDR3 secretes O-methylated coumarins in response to iron deficiency.	Coumarins	67-76	pleiotropic drug resistance protein 3	Nicotiana tabacum	38-44
29893871-4	2018	Metabolic profiling of roots and root exudates revealed that, upon iron deficiency, secretion of catechol-bearing O-methylated coumarins such as fraxetin, hydroxyfraxetin, and methoxyfraxetin to the rhizosphere was compromised in NtPDR3-silenced plants.	Coumarins	127-136	pleiotropic drug resistance protein 3	Nicotiana tabacum	230-236
30388753-7	2018	We evaluated the effects of other coumarins and found that the prenyl group, which binds at the 8-position of coumarins, plays an important role in the inhibition of URAT1.	Coumarins	34-43	solute carrier family 22 member 12	Homo sapiens	166-171
30388753-7	2018	We evaluated the effects of other coumarins and found that the prenyl group, which binds at the 8-position of coumarins, plays an important role in the inhibition of URAT1.	Coumarins	110-119	solute carrier family 22 member 12	Homo sapiens	166-171
30583637-7	2018	In this study, the analysis of metabolites of three coumarins basically demonstrated their in vivo metabolic process, providing basis for the further pharmacokinetics and pharmacological evaluations of SC-1, SC-2 and IS-1.	Coumarins	52-61	PR/SET domain 4	Rattus norvegicus	202-206
30583637-7	2018	In this study, the analysis of metabolites of three coumarins basically demonstrated their in vivo metabolic process, providing basis for the further pharmacokinetics and pharmacological evaluations of SC-1, SC-2 and IS-1.	Coumarins	52-61	trans-2,3-enoyl-CoA reductase	Rattus norvegicus	208-212
29893871-7	2018	The results demonstrate that N. tabacum secretes both coumarins and flavins in response to iron deficiency and that NtPDR3 plays an essential role in the plant response to iron deficiency by mediating secretion of O-methylated coumarins to the rhizosphere.	Coumarins	227-236	pleiotropic drug resistance protein 3	Nicotiana tabacum	116-122
29772410-1	2018	Coumarins and meroterpene from the fruits of Cullen corylifolium were evaluated for their ability to bind and activate human estrogen receptor alpha (hERalpha) by a combination of in vitro studies and molecular dynamics simulations.	Coumarins	0-9	Era like 12S mitochondrial rRNA chaperone 1	Homo sapiens	150-158
29772410-2	2018	The recombinant hERalpha ligand binding domain (hERalpha-LBD) was produced in BL21 (DE3)pLysS and the fluorescence polarization (FP) assay was performed to determine the binding affinities of coumarins and meroterpene with receptor protein.	Coumarins	192-201	Era like 12S mitochondrial rRNA chaperone 1	Homo sapiens	16-24
29772410-2	2018	The recombinant hERalpha ligand binding domain (hERalpha-LBD) was produced in BL21 (DE3)pLysS and the fluorescence polarization (FP) assay was performed to determine the binding affinities of coumarins and meroterpene with receptor protein.	Coumarins	192-201	Era like 12S mitochondrial rRNA chaperone 1	Homo sapiens	48-56
29772410-4	2018	In an estrogen response element-luciferase (ERE-Luc) reporter gene assay, coumarins and meroterpene acted as agonists of human estrogen receptor alpha.	Coumarins	74-83	estrogen receptor 1	Homo sapiens	127-150
29772410-6	2018	Coumarins and meroterpene adopted an agonist conformation within the cavity of hERalpha-LBD.	Coumarins	0-9	Era like 12S mitochondrial rRNA chaperone 1	Homo sapiens	79-87
29675887-3	2018	As noted from the literature, sulfocoumarin (1,2-benzoxathiine 2,2-dioxide) acts as a "prodrug" inhibitor and is hydrolyzed by the esterase activity of hCA to form 2-hydroxyphenylvinylsulfonic acid, which thereafter binds to the enzyme in a manner similar to that of coumarins and sulfoxocoumarins.	Coumarins	267-276	HCA1	Homo sapiens	152-155
29309875-3	2018	Herein, we predicted the drug likeness of six coumarins with high affinity towards 5-HT1A and 5-HT2A receptors.	Coumarins	46-55	5-hydroxytryptamine receptor 1A	Homo sapiens	83-95
29730190-1	2018	Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor beta and aryl hydrocarbon receptor.	Coumarins	20-29	estrogen receptor 2 (beta)	Mus musculus	229-251
29730190-1	2018	Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor beta and aryl hydrocarbon receptor.	Coumarins	20-29	aryl-hydrocarbon receptor	Mus musculus	256-281
29675519-0	2018	Peroxy mediated Csp2-Csp3 dehydrogenative coupling: regioselective functionalization of coumarins and coumarin-3-carboxylic acids.	Coumarins	88-97	regulator of calcineurin 2	Homo sapiens	16-20
29675519-1	2018	A regioselective direct alkylation of coumarins at C-3 via cross-dehydrogenative coupling of unactivated Csp2-Csp3 bonds is developed.	Coumarins	38-47	complement C3	Homo sapiens	51-54
29675519-1	2018	A regioselective direct alkylation of coumarins at C-3 via cross-dehydrogenative coupling of unactivated Csp2-Csp3 bonds is developed.	Coumarins	38-47	regulator of calcineurin 2	Homo sapiens	105-109
29940744-12	2018	CONCLUSION: The results are indicative of a distinctive cytotoxic mechanism for 7f compared to other coumarins, possibly due to its 15-LOX-1 inhibitory potential.	Coumarins	101-110	arachidonate 15-lipoxygenase	Homo sapiens	132-140
29685682-1	2018	4-Coumaroyl-CoA ligase (4CL) is ubiquitous in the plant kingdom, and plays a central role in the biosynthesis of phenylpropanoids such as lignins, flavonoids, and coumarins.	Coumarins	163-172	4-coumarate--CoA ligase-like 7-like	Glycine max	0-22
29685682-1	2018	4-Coumaroyl-CoA ligase (4CL) is ubiquitous in the plant kingdom, and plays a central role in the biosynthesis of phenylpropanoids such as lignins, flavonoids, and coumarins.	Coumarins	163-172	4-coumarate--CoA ligase-like 7-like	Glycine max	24-27
29309875-3	2018	Herein, we predicted the drug likeness of six coumarins with high affinity towards 5-HT1A and 5-HT2A receptors.	Coumarins	46-55	5-hydroxytryptamine receptor 2A	Homo sapiens	96-100
29327585-4	2018	In addition, synthetic coumarins were investigated for 5alpha-dihydrotestosterone (DHT)-induced secretion of prostate-specific antigen (PSA) levels and cell proliferation of androgen-dependent CWR22Rv1 cells.	Coumarins	23-32	kallikrein related peptidase 3	Homo sapiens	109-140
29285772-2	2018	Several classes of natural products including coumarins and flavonoids have shown remarkable Glo-I inhibitory activity.	Coumarins	46-55	glyoxalase I	Homo sapiens	93-98
28464781-9	2018	Coumarins inhibited all these parameters except for IL-10, nuclear factor erythroid 2 (NFE2)-related-factor 2 (Nrf2), and regulatory T cell (Treg) differentiation.	Coumarins	0-9	interleukin 10	Homo sapiens	52-57
28641473-3	2018	Here we describe the anti-tumoral effects of a new class of CAXII inhibitors, the glycosyl coumarins on T-ALL/LL cells.	Coumarins	91-100	carbonic anhydrase 12	Homo sapiens	60-65
28464781-9	2018	Coumarins inhibited all these parameters except for IL-10, nuclear factor erythroid 2 (NFE2)-related-factor 2 (Nrf2), and regulatory T cell (Treg) differentiation.	Coumarins	0-9	nuclear factor, erythroid 2	Homo sapiens	59-85
28464781-9	2018	Coumarins inhibited all these parameters except for IL-10, nuclear factor erythroid 2 (NFE2)-related-factor 2 (Nrf2), and regulatory T cell (Treg) differentiation.	Coumarins	0-9	NFE2 like bZIP transcription factor 2	Homo sapiens	111-115
28464781-11	2018	The results showed that coumarins exerted antiinflammatory and antioxidant activities by inhibiting NF-kappaB, nuclear factor of activated T cells (NFAT), retinoic acid-related orphan receptor gammatau (RORgammatau), and MAPK and increasing Nrf2 activation.	Coumarins	24-33	NFE2 like bZIP transcription factor 2	Homo sapiens	241-245
28807721-0	2017	Selenopheno quinolinones and coumarins promote cancer cell apoptosis by ROS depletion and caspase-7 activation.	Coumarins	29-38	caspase 7	Homo sapiens	90-99
29218011-5	2017	A higher proportion of novel-to-known variants for 10 genes was identified on 41 core pharmacogenomics genes related to the PK (29), PD (3), of coumarins, and coagulation proteins (9) including, CYP1A1, CYP3A4, CYP3A5, and F8, and a low proportion of novel-to-known variants on CYP2E1, VKORC1, and SULT1A1/2.	Coumarins	144-153	cytochrome P450 family 1 subfamily A member 1	Homo sapiens	195-201
29218011-5	2017	A higher proportion of novel-to-known variants for 10 genes was identified on 41 core pharmacogenomics genes related to the PK (29), PD (3), of coumarins, and coagulation proteins (9) including, CYP1A1, CYP3A4, CYP3A5, and F8, and a low proportion of novel-to-known variants on CYP2E1, VKORC1, and SULT1A1/2.	Coumarins	144-153	cytochrome P450 family 3 subfamily A member 4	Homo sapiens	203-209
29218011-5	2017	A higher proportion of novel-to-known variants for 10 genes was identified on 41 core pharmacogenomics genes related to the PK (29), PD (3), of coumarins, and coagulation proteins (9) including, CYP1A1, CYP3A4, CYP3A5, and F8, and a low proportion of novel-to-known variants on CYP2E1, VKORC1, and SULT1A1/2.	Coumarins	144-153	cytochrome P450 family 3 subfamily A member 5	Homo sapiens	211-217
29218011-5	2017	A higher proportion of novel-to-known variants for 10 genes was identified on 41 core pharmacogenomics genes related to the PK (29), PD (3), of coumarins, and coagulation proteins (9) including, CYP1A1, CYP3A4, CYP3A5, and F8, and a low proportion of novel-to-known variants on CYP2E1, VKORC1, and SULT1A1/2.	Coumarins	144-153	cytochrome P450 family 2 subfamily E member 1	Homo sapiens	278-284
29218011-5	2017	A higher proportion of novel-to-known variants for 10 genes was identified on 41 core pharmacogenomics genes related to the PK (29), PD (3), of coumarins, and coagulation proteins (9) including, CYP1A1, CYP3A4, CYP3A5, and F8, and a low proportion of novel-to-known variants on CYP2E1, VKORC1, and SULT1A1/2.	Coumarins	144-153	vitamin K epoxide reductase complex subunit 1	Homo sapiens	286-292
29218011-5	2017	A higher proportion of novel-to-known variants for 10 genes was identified on 41 core pharmacogenomics genes related to the PK (29), PD (3), of coumarins, and coagulation proteins (9) including, CYP1A1, CYP3A4, CYP3A5, and F8, and a low proportion of novel-to-known variants on CYP2E1, VKORC1, and SULT1A1/2.	Coumarins	144-153	sulfotransferase family 1A member 1	Homo sapiens	298-307
29044437-1	2017	Coumarins are natural and synthetic active ingredients widely applied in diverse types of medicinal treatments, such as cancer, inflammation, infection, and enzyme inhibition (monoamine oxidase B).	Coumarins	0-9	monoamine oxidase B	Homo sapiens	176-195
29085929-4	2017	To demonstrate potential applications of this fluorogenic reaction, we synthesized a semicarbazide-presenting amino acid d-Dap-Scz, which readily incorporates into the cell wall of Staphalococcus aureus and serves as a handle for conjugation with the coumarins.	Coumarins	251-260	death associated protein	Homo sapiens	123-126
29085929-5	2017	The fluorogenic conjugation of the coumarins to cell surface semicarbazide enables facile visualization of d-Dap-Scz treated bacteria.	Coumarins	35-44	death associated protein	Homo sapiens	109-112
28807721-7	2017	CONCLUSION: This present study provides scientific evidence that selenopheno quinolinones and coumarins promote cancer cell apoptosis by ROS depletion and caspase-7 activation in malignant cells.	Coumarins	94-103	caspase 7	Homo sapiens	155-164
28441483-2	2017	We have reported recently the identification of small molecules (coumarins, iso-coumarins and pyrido-pyrimidinones) that modify the alternative splicing of SMN2, a paralogous gene to SMN1, restoring the survival motor neuron (SMN) protein level in mouse models of SMA.	Coumarins	65-74	survival motor neuron 1	Mus musculus	183-187
28623273-0	2017	Arabidopsis Transporter ABCG37/PDR9 contributes primarily highly oxygenated Coumarins to Root Exudation.	Coumarins	76-85	pleiotropic drug resistance 9	Arabidopsis thaliana	24-30
28623273-0	2017	Arabidopsis Transporter ABCG37/PDR9 contributes primarily highly oxygenated Coumarins to Root Exudation.	Coumarins	76-85	pleiotropic drug resistance 9	Arabidopsis thaliana	31-35
28623273-7	2017	The specificity of ABCG37 for individual coumarins was further verified by a targeted LC-MS based coumarin profiling method.	Coumarins	41-50	pleiotropic drug resistance 9	Arabidopsis thaliana	19-25
28623273-9	2017	In either treatment, the distribution of individual coumarins between roots and exudates in the investigated genotypes suggested the involvement of ABCG37 in the exudation specifically of highly oxygenated rather than monohydroxylated coumarins.	Coumarins	52-61	pleiotropic drug resistance 9	Arabidopsis thaliana	148-154
28623273-9	2017	In either treatment, the distribution of individual coumarins between roots and exudates in the investigated genotypes suggested the involvement of ABCG37 in the exudation specifically of highly oxygenated rather than monohydroxylated coumarins.	Coumarins	235-244	pleiotropic drug resistance 9	Arabidopsis thaliana	148-154
28441483-2	2017	We have reported recently the identification of small molecules (coumarins, iso-coumarins and pyrido-pyrimidinones) that modify the alternative splicing of SMN2, a paralogous gene to SMN1, restoring the survival motor neuron (SMN) protein level in mouse models of SMA.	Coumarins	65-74	glutamate receptor, metabotropic 7	Mus musculus	156-160
28586696-2	2017	Prothrombin time (PT) International Normalized Ratio (INR) monitoring is fundamental to establish coumarins dosage and prevent bleeding complications or thrombotic events.	Coumarins	98-107	coagulation factor II, thrombin	Homo sapiens	0-11
28445814-4	2017	In the present study, a method based on the modified mass defect filter (MDF) was firstly developed and validated for comprehensive profiling of coumarins in the different parts of CNO via ultra-performance liquid chromatography tandem quadrupole time-of-flight mass spectrometry (UPLC-QTOF/MS).	Coumarins	145-154	biogenesis of lysosomal organelles complex 1 subunit 4	Homo sapiens	181-184
28445814-6	2017	The fragmentation behavior of coumarins was systematically investigated and a total of 42 coumarins including 27 potential new ones were unambiguously or tentatively identified in the CNO.	Coumarins	30-39	biogenesis of lysosomal organelles complex 1 subunit 4	Homo sapiens	184-187
28445814-6	2017	The fragmentation behavior of coumarins was systematically investigated and a total of 42 coumarins including 27 potential new ones were unambiguously or tentatively identified in the CNO.	Coumarins	90-99	biogenesis of lysosomal organelles complex 1 subunit 4	Homo sapiens	184-187
28233981-7	2017	All four dyes could be used to make the epoxy fluorescent, but coumarins 1 and 2 slightly reduced the lap shear strength of the thermoset and could be extracted with solvent.	Coumarins	63-72	LAP	Homo sapiens	102-105
28330723-9	2017	RESULTS: The chromatographic profile of AEPp indicated the presence of flavonoids, coumarins and hydrolyzable and condensed tannins.	Coumarins	83-92	immunoglobulin mu DNA binding protein 2	Rattus norvegicus	40-44
28254487-0	2017	Synthesis and biological evaluation of C-3 aliphatic coumarins as vitamin K antagonists.	Coumarins	53-62	complement C3	Homo sapiens	39-42
27915078-0	2017	Analgesic effect of coumarins from Radix angelicae pubescentis is mediated by inflammatory factors and TRPV1 in a spared nerve injury model of neuropathic pain.	Coumarins	20-29	transient receptor potential cation channel, subfamily V, member 1	Rattus norvegicus	103-108
28101548-1	2017	Preorientation of the terminal coumarins of a crown ether with the assistance of taco-type host-guest complex formation promotes regio- and stereo-selectivity of coumarin photodimerization to give only the syn head-to-tail coumarin isomer.	Coumarins	31-40	coronin 1A	Homo sapiens	81-85
28101548-1	2017	Preorientation of the terminal coumarins of a crown ether with the assistance of taco-type host-guest complex formation promotes regio- and stereo-selectivity of coumarin photodimerization to give only the syn head-to-tail coumarin isomer.	Coumarins	31-40	synemin	Homo sapiens	206-209
27988397-0	2017	Total coumarins of Hedyotis diffusa induces apoptosis of myelodysplastic syndrome SKM-1 cells by activation of caspases and inhibition of PI3K/Akt pathway proteins.	Coumarins	6-15	sodium voltage-gated channel alpha subunit 4	Homo sapiens	82-87
26586254-3	2016	The quinolinone conjugates were inactive as enzyme inhibitors, whereas the coumarins were ineffective hCA I/II inhibitors (KIs > 50 muM) but were submicromolar hCA IV and XII inhibitors, with inhibition constants ranging between 92 nM and 1.19 muM for hCA IV, and between 0.11 and 0.79 muM for hCA XII.	Coumarins	75-84	carbonic anhydrase 4	Homo sapiens	163-169
27456663-9	2017	However, in the zVAD pretreated cells, necroptotic cell death with a significant increase in expression of RIP1, RIP3, and MLKL genes was observed Conclusion: The novel hybrid benzoxazole-coumarins effectively induce Caspase-3 dependent apoptosis in HN-5 cancer cells, but also could circumvent the blockage of apoptotic cell death by induction of necroptosis.	Coumarins	188-197	receptor interacting serine/threonine kinase 1	Homo sapiens	107-111
27456663-9	2017	However, in the zVAD pretreated cells, necroptotic cell death with a significant increase in expression of RIP1, RIP3, and MLKL genes was observed Conclusion: The novel hybrid benzoxazole-coumarins effectively induce Caspase-3 dependent apoptosis in HN-5 cancer cells, but also could circumvent the blockage of apoptotic cell death by induction of necroptosis.	Coumarins	188-197	receptor interacting serine/threonine kinase 3	Homo sapiens	113-117
27456663-9	2017	However, in the zVAD pretreated cells, necroptotic cell death with a significant increase in expression of RIP1, RIP3, and MLKL genes was observed Conclusion: The novel hybrid benzoxazole-coumarins effectively induce Caspase-3 dependent apoptosis in HN-5 cancer cells, but also could circumvent the blockage of apoptotic cell death by induction of necroptosis.	Coumarins	188-197	mixed lineage kinase domain like pseudokinase	Homo sapiens	123-127
27456663-9	2017	However, in the zVAD pretreated cells, necroptotic cell death with a significant increase in expression of RIP1, RIP3, and MLKL genes was observed Conclusion: The novel hybrid benzoxazole-coumarins effectively induce Caspase-3 dependent apoptosis in HN-5 cancer cells, but also could circumvent the blockage of apoptotic cell death by induction of necroptosis.	Coumarins	188-197	caspase 3	Homo sapiens	217-226
28245770-4	2017	Chromones are structurally related to a series of coumarins and chalcones, which are well-known inhibitors of MAO-B.	Coumarins	50-59	monoamine oxidase B	Homo sapiens	110-115
29243580-0	2017	Coumarins as Promising Scaffold for the Treatment of Age-related Diseases - An Overview of the Last Five Years.	Coumarins	0-9	renin binding protein	Homo sapiens	53-56
29243580-10	2017	This review provides an overview of the last five years about the potential of coumarins as modulators of several physiological mechanisms involved in age-related pathologies.	Coumarins	79-88	renin binding protein	Homo sapiens	151-154
26887799-0	2016	Some coumarins and benzoxazinones as potent paraoxonase 1 inhibitors.	Coumarins	5-14	paraoxonase 1	Homo sapiens	44-57
26586254-3	2016	The quinolinone conjugates were inactive as enzyme inhibitors, whereas the coumarins were ineffective hCA I/II inhibitors (KIs > 50 muM) but were submicromolar hCA IV and XII inhibitors, with inhibition constants ranging between 92 nM and 1.19 muM for hCA IV, and between 0.11 and 0.79 muM for hCA XII.	Coumarins	75-84	carbonic anhydrase 4	Homo sapiens	255-261
26586254-3	2016	The quinolinone conjugates were inactive as enzyme inhibitors, whereas the coumarins were ineffective hCA I/II inhibitors (KIs > 50 muM) but were submicromolar hCA IV and XII inhibitors, with inhibition constants ranging between 92 nM and 1.19 muM for hCA IV, and between 0.11 and 0.79 muM for hCA XII.	Coumarins	75-84	carbonic anhydrase 12	Homo sapiens	297-304
26833890-8	2016	Overall, these results lead to discovery of fused tricyclic coumarins as promising dual binding site inhibitors of acetylcholinesterase and afford multifunctional compounds with potential impact for further pharmacological development in Alzheimer"s therapy.	Coumarins	60-69	acetylcholinesterase (Cartwright blood group)	Homo sapiens	115-135
27907087-7	2016	As a result, we identified 3 mammea coumarins that efficiently reduce (up to >90% at 10 muM) both basal and cytokine-regulated levels of MHC class I, class II, MICA and HLA-E on EC surface.	Coumarins	36-45	MHC class I polypeptide-related sequence A	Homo sapiens	163-167
27907087-7	2016	As a result, we identified 3 mammea coumarins that efficiently reduce (up to >90% at 10 muM) both basal and cytokine-regulated levels of MHC class I, class II, MICA and HLA-E on EC surface.	Coumarins	36-45	major histocompatibility complex, class I, E	Homo sapiens	172-177
27907087-11	2016	In conclusion, mammea coumarins with a free prenyl group and the PPAP guttiferone J emerge as NPs able to drastically decrease both VCAM-1 and a set of MHC molecules and to potentially reduce the immunogenicity of the endothelium.	Coumarins	22-31	vascular cell adhesion molecule 1	Homo sapiens	132-138
27788333-1	2016	A regioselective synthesis of naphtho[2,1,8-def]coumarins has been realized through a concise route that involves the intramolecular Friedel-Crafts reaction of benzo[f]coumarins.	Coumarins	48-57	UTP25 small subunit processome component	Homo sapiens	44-47
27788333-7	2016	Photophysical studies revealed that 5-hydroxy-naphtho[2,1,8-def]coumarin has the most bathochromically shifted both absorption and emission among all pi-expanded coumarins bearing one OH functionality.	Coumarins	162-171	UTP25 small subunit processome component	Homo sapiens	60-63
27473958-2	2016	The present study was designed to investigate the in vitro effects of estrogen-like activities of two widespread coumarins, osthole and imperatorin, using the MCF-7 cell proliferation assay and their alkaline phosphatase (ALP) activities in osteoblasts Saos-2 cells.	Coumarins	113-122	alkaline phosphatase, placental	Homo sapiens	200-220
26750618-0	2016	Functionalized Coumarine Fragment to Obtain Fluorescent and Selective P-Glycoprotein Ligands.	Coumarins	15-24	ATP binding cassette subfamily B member 1	Homo sapiens	70-84
27053426-1	2016	Sulfated Coumarins Induce Regulation, not just Inhibition, of Thrombin.	Coumarins	9-18	coagulation factor II, thrombin	Homo sapiens	62-70
27053426-4	2016	We synthesized a focused library of some 36 sulfated coumarins to discover two agents that display sub-maximal efficacy (~50%), high potency (<500 nM) and high selectivity for thrombin (>150-fold).	Coumarins	53-62	coagulation factor II, thrombin	Homo sapiens	179-187
27053426-7	2016	Antithrombin inactivation of thrombin was impaired in the presence of the sulfated coumarins suggesting that allosteric partial inhibition arises from catalytic dysfunction of the active site.	Coumarins	83-92	serpin family C member 1	Homo sapiens	0-12
27053426-7	2016	Antithrombin inactivation of thrombin was impaired in the presence of the sulfated coumarins suggesting that allosteric partial inhibition arises from catalytic dysfunction of the active site.	Coumarins	83-92	coagulation factor II, thrombin	Homo sapiens	4-12
27053426-8	2016	Overall, sulfated coumarins represent first-in-class, sub-maximal inhibitors of thrombin.	Coumarins	18-27	coagulation factor II, thrombin	Homo sapiens	80-88
26750618-1	2016	Starting from our lead compound MC70 displaying high P-glycoprotein (P-gp) inhibition activity but low selectivity, a new class of coumarine derivatives was studied to develop selective and fluorescent P-gp ligands.	Coumarins	131-140	ATP binding cassette subfamily B member 1	Homo sapiens	202-206
26750618-2	2016	In this series, the biphenyl moiety of MC70 was replaced with the coumarine fluorophore as a bioisostere of the biphenyl nucleus in order to improve the selectivity toward P-gp and the fluorescent properties for in vitro studies.	Coumarins	66-75	ATP binding cassette subfamily B member 1	Homo sapiens	172-176
26750618-3	2016	Moreover, the presence and position of substituents on the coumarine nucleus were probed to develop suitable fluorescent probes to study the expression and activity of P-gp in living cells.	Coumarins	59-68	ATP binding cassette subfamily B member 1	Homo sapiens	168-172
26688270-2	2016	The X-ray crystal structure of 6-hydroxy-2-thioxocoumarin bound to hCA II revealed an unprecedented and unexpected inhibition mechanism for this new class of inhibitors when compared to isostructural coumarins.	Coumarins	200-209	carbonic anhydrase 2	Homo sapiens	67-73
26432607-4	2015	Most of the coumarins were weak inhibitors or did not inhibit significantly hCA I and II, but showed low nanomolar inhibitory action against the transmembrane isoforms (K(I) of 14.3-34.4 nM against hCA IX and of 4.7-37.8 nM against hCA XII).	Coumarins	12-21	cytochrome P450 family 24 subfamily A member 1	Homo sapiens	76-88
27185570-11	2016	The finding that newly designed coumarins can be exploited for inhibition of P-gp mediated efflux in order to enhance paclitaxel bioavailability and can inhibit breast cancer stem cell growth is significant for designing potent anticancer drugs.	Coumarins	32-41	ATP binding cassette subfamily B member 1	Homo sapiens	77-81
24993184-0	2015	Cytochrome P450 isoenzymes in rat and human liver microsomes associate with the metabolism of total coumarins in Fructus Cnidii.	Coumarins	100-109	cytochrome P450, family 2, subfamily g, polypeptide 1	Rattus norvegicus	0-15
26231923-9	2015	CYP1C1 and CYP1C2 dealkylated substituted coumarins and ethoxy-fluorescein-ethylester, while CYP1D1 did not.	Coumarins	42-51	cytochrome P450, family 1, subfamily C, polypeptide 1	Danio rerio	0-6
26231923-9	2015	CYP1C1 and CYP1C2 dealkylated substituted coumarins and ethoxy-fluorescein-ethylester, while CYP1D1 did not.	Coumarins	42-51	cytochrome P450, family 1, subfamily C, polypeptide 2	Danio rerio	11-17
26432607-4	2015	Most of the coumarins were weak inhibitors or did not inhibit significantly hCA I and II, but showed low nanomolar inhibitory action against the transmembrane isoforms (K(I) of 14.3-34.4 nM against hCA IX and of 4.7-37.8 nM against hCA XII).	Coumarins	12-21	carbonic anhydrase 9	Homo sapiens	198-204
26432607-4	2015	Most of the coumarins were weak inhibitors or did not inhibit significantly hCA I and II, but showed low nanomolar inhibitory action against the transmembrane isoforms (K(I) of 14.3-34.4 nM against hCA IX and of 4.7-37.8 nM against hCA XII).	Coumarins	12-21	carbonic anhydrase 12	Homo sapiens	232-239
26366750-4	2015	Our data revealed that total coumarins inhibited high glucose-induced HBZY-1 cell proliferation and hypertrophy, and produced its effects through downregulating transforming growth factor-beta1, connective tissue growth factor, and toll-like receptor 4 activation.	Coumarins	29-38	transforming growth factor, beta 1	Rattus norvegicus	161-193
26366750-4	2015	Our data revealed that total coumarins inhibited high glucose-induced HBZY-1 cell proliferation and hypertrophy, and produced its effects through downregulating transforming growth factor-beta1, connective tissue growth factor, and toll-like receptor 4 activation.	Coumarins	29-38	cellular communication network factor 2	Rattus norvegicus	195-252
26314757-0	2015	Comparative inhibitory effect of prenylated coumarins, ferulenol and ferprenin, contained in the "poisonous chemotype" of Ferula communis on mammal liver microsomal VKORC1 activity.	Coumarins	44-53	vitamin K epoxide reductase complex subunit 1	Homo sapiens	165-171
26366750-6	2015	Total coumarins, at a dose of 50 or 100 mg/kg: 1) significantly increased body weight; 2) ameliorated morphological evidence of renal pathology; 3) decreased blood levels of glucose and urea nitrogen; 4) decreased albuminuria and serum creatinine; and 5) reduced protein and gene levels of transforming growth factor-beta1, connective tissue growth factor, and toll-like receptor 4 in the kidneys.	Coumarins	6-15	transforming growth factor, beta 1	Rattus norvegicus	290-322
26366750-6	2015	Total coumarins, at a dose of 50 or 100 mg/kg: 1) significantly increased body weight; 2) ameliorated morphological evidence of renal pathology; 3) decreased blood levels of glucose and urea nitrogen; 4) decreased albuminuria and serum creatinine; and 5) reduced protein and gene levels of transforming growth factor-beta1, connective tissue growth factor, and toll-like receptor 4 in the kidneys.	Coumarins	6-15	cellular communication network factor 2	Rattus norvegicus	324-381
26594765-3	2015	All flavonoids and coumarins showed significant alpha-glucosidase inhibitory activity, while amentoflavone gave a positive result against 15-lipoxygenase inhibition.	Coumarins	19-28	sucrase-isomaltase	Homo sapiens	48-65
26188907-0	2015	Coumarins as anticancer agents: a review on synthetic strategies, mechanism of action and SAR studies.	Coumarins	0-9	sarcosine dehydrogenase	Homo sapiens	90-93
26221081-8	2015	Additionally, both coumarins inhibited the LPS-induced protein and mRNA expression levels of nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in RAW264.7 cells.	Coumarins	19-28	nitric oxide synthase 2, inducible	Mus musculus	116-120
26221081-8	2015	Additionally, both coumarins inhibited the LPS-induced protein and mRNA expression levels of nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in RAW264.7 cells.	Coumarins	19-28	prostaglandin-endoperoxide synthase 2	Mus musculus	126-142
26221081-12	2015	Furthermore, both coumarins significantly inhibited c-Jun expression in the nucleus.	Coumarins	18-27	jun proto-oncogene	Mus musculus	52-57
26221081-8	2015	Additionally, both coumarins inhibited the LPS-induced protein and mRNA expression levels of nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in RAW264.7 cells.	Coumarins	19-28	prostaglandin-endoperoxide synthase 2	Mus musculus	144-149
25592709-0	2015	Novel synthetic coumarins that targets NF-kappaB in Hepatocellular carcinoma.	Coumarins	16-25	nuclear factor kappa B subunit 1	Homo sapiens	39-48
25843566-4	2015	A deeper insight into the structure-activity relationship of sesquiterpene coumarins revealed that ring-opened drimane-type sesquiterpene coumarins including farnesiferol B, farnesiferol C and lehmferin possessed the best inhibitory effects on P-gp pump efflux and they could be considered as lead scaffolds for further structure modifications.	Coumarins	75-84	phosphoglycolate phosphatase	Homo sapiens	244-248
25843566-4	2015	A deeper insight into the structure-activity relationship of sesquiterpene coumarins revealed that ring-opened drimane-type sesquiterpene coumarins including farnesiferol B, farnesiferol C and lehmferin possessed the best inhibitory effects on P-gp pump efflux and they could be considered as lead scaffolds for further structure modifications.	Coumarins	138-147	phosphoglycolate phosphatase	Homo sapiens	244-248
25658804-9	2015	In addition, coumarins may hinder the induction of inducible NO-synthase and cyclooxygenase- 2.	Coumarins	13-22	nitric oxide synthase 2	Homo sapiens	51-72
25312586-12	2015	VO and/or Cou could inhibit the expression of the tight junction protein, ZO-1 and actin.	Coumarins	10-13	tight junction protein 1	Homo sapiens	50-78
25312586-13	2015	VO and/or Cou also could inhibit the expression of P-gp.	Coumarins	10-13	phosphoglycolate phosphatase	Homo sapiens	51-55
26081557-7	2015	Docking studies revealed that 3-pyrazolyl substituted coumarins make key interactions with residues at active site of JNK1.	Coumarins	54-63	mitogen-activated protein kinase 8	Homo sapiens	118-122
25915613-0	2015	Coumarins: Auspicious Cholinesterase and Monoamine Oxidase Inhibitors.	Coumarins	0-9	butyrylcholinesterase	Homo sapiens	22-36
25915613-3	2015	Coumarins, beside their employment in other pharmacological groups, have also attracted attention to be utilized in cholinesterase inhibitory molecule discovery and development.	Coumarins	0-9	butyrylcholinesterase	Homo sapiens	116-130
25658804-9	2015	In addition, coumarins may hinder the induction of inducible NO-synthase and cyclooxygenase- 2.	Coumarins	13-22	prostaglandin-endoperoxide synthase 2	Homo sapiens	77-94
25260115-1	2014	The room-temperature oxidative C-H/C-H cross-couplings between (hetero)arenes and alkenes, coumarins or quinones have been reported by using a highly electrophilic palladium species [Pd(TFA)2], generated in situ from Pd(OAc)2 and TFA, as the catalyst and cheap (NH4)2S2O8 as the oxidant under air.	Coumarins	91-100	churchill domain containing 1	Homo sapiens	31-38
25755702-1	2015	Coumarins induce apoptosis by activating mitochondrial pathway and caspase-3-dependent apoptotic pathway.	Coumarins	0-9	caspase 3	Homo sapiens	67-76
24934993-1	2014	Naturally occurring coumarins, having wide spectrum of activities such as antioxidant, anti-inflammatory, anticancer, MAO-B inhibitory and antimicrobial, are frequently used by the researchers to develop novel synthetic and semisynthetic coumarin based therapeutic agents.	Coumarins	20-29	monoamine oxidase B	Homo sapiens	118-123
24549088-0	2014	Manganese(III)-mediated direct Csp2-H radical trifluoromethylation of coumarins with sodium trifluoromethanesulfinate.	Coumarins	70-79	regulator of calcineurin 2	Homo sapiens	31-35
24681028-3	2014	This work reports the semisynthesis, ex vivo relaxing evaluation and SAR studies of a series of 18 coumarins.	Coumarins	99-108	sarcosine dehydrogenase	Homo sapiens	69-72
23488741-2	2014	These coumarins were very weak or ineffective as inhibitors of the house-keeping, offtarget isoforms CA I and II, but showed effective, submicromolar inhibition of the transmembrane, tumor-associated isoforms CA IX and to a slightly less extent, CA XII.	Coumarins	6-15	carbonic anhydrase 1	Homo sapiens	101-105
23488741-2	2014	These coumarins were very weak or ineffective as inhibitors of the house-keeping, offtarget isoforms CA I and II, but showed effective, submicromolar inhibition of the transmembrane, tumor-associated isoforms CA IX and to a slightly less extent, CA XII.	Coumarins	6-15	carbonic anhydrase 9	Homo sapiens	209-214
23488741-2	2014	These coumarins were very weak or ineffective as inhibitors of the house-keeping, offtarget isoforms CA I and II, but showed effective, submicromolar inhibition of the transmembrane, tumor-associated isoforms CA IX and to a slightly less extent, CA XII.	Coumarins	6-15	carbonic anhydrase 12	Homo sapiens	246-252
24337438-10	2014	Studies are required to know whether fluindione could be an alternative VKA in carriers of polymorphic CYP2C9 alleles, hypersensitive to coumarins.	Coumarins	137-146	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	103-109
24782464-6	2014	6-Chloro-3-phenylcoumarins unsubstituted at the 4 position were found to be more active as MAO-B inhibitors than the corresponding 4-hydroxylated coumarins.	Coumarins	17-26	monoamine oxidase B	Homo sapiens	91-96
24549088-1	2014	Mn(OAc)3-mediated direct Csp2-H radical trifluoromethylation of coumarins with CF3SO2Na (Langlois reagent) to afford selective 3-trifluoromethyl coumarins in moderate to good yields is described.	Coumarins	64-73	regulator of calcineurin 2	Homo sapiens	25-29
24492725-4	2014	Coumarins, flavonols, and catechin inhibited hMATE1 activity.	Coumarins	0-9	solute carrier family 47 member 1	Homo sapiens	45-51
24393810-1	2014	A series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones (coumarins) have been synthesized and their inhibitory activity to human monoamine oxidase A (MAO A) and B (MAO B) determined.	Coumarins	67-76	monoamine oxidase A	Homo sapiens	139-158
24393810-1	2014	A series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones (coumarins) have been synthesized and their inhibitory activity to human monoamine oxidase A (MAO A) and B (MAO B) determined.	Coumarins	67-76	monoamine oxidase A	Homo sapiens	160-165
24393810-1	2014	A series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones (coumarins) have been synthesized and their inhibitory activity to human monoamine oxidase A (MAO A) and B (MAO B) determined.	Coumarins	67-76	monoamine oxidase B	Homo sapiens	174-179
25338981-7	2014	Subsequently, we provide a generalized view of considerable biological activity of coumarins against a wide range of cancer cell lines and how coumarins (psoralidin and esculetin) isolated from natural sources have improved TRAIL induced apoptosis in resistant cancer cells.	Coumarins	143-152	TNF superfamily member 10	Homo sapiens	224-229
24103856-3	2013	In this report, we have studied the effect of 7,8-diacetoxy-4-methylcoumarin (DAMC, a model PA) and other acetoxy coumarins on the thioredoxin and VEGF expression in human peripheral blood mononuclear cells (PBMCs), with a view to substantiate our earlier observation that DAMC was a superb inducer of angiogenesis.	Coumarins	114-123	thioredoxin	Homo sapiens	131-142
24083611-5	2014	According to their structural features, CYP1 inhibitors are divided into the following categories: flavonoids, trans-stilbenes, coumarins, terpenoids, alkaloids, quinones, isothiocyanates and synthetic aromatics.	Coumarins	128-137	cytochrome P450 family 27 subfamily B member 1	Homo sapiens	40-44
24103856-3	2013	In this report, we have studied the effect of 7,8-diacetoxy-4-methylcoumarin (DAMC, a model PA) and other acetoxy coumarins on the thioredoxin and VEGF expression in human peripheral blood mononuclear cells (PBMCs), with a view to substantiate our earlier observation that DAMC was a superb inducer of angiogenesis.	Coumarins	114-123	vascular endothelial growth factor A	Homo sapiens	147-151
24103856-5	2013	The fact that TRX activity of PBMCs was enhanced by various acetoxy coumarins in tune with their affinity to CRTAase as substrate, suggested the possible activation of TRX due to acetylation.	Coumarins	68-77	thioredoxin	Homo sapiens	14-17
23994743-6	2013	Oxidation of the hydroxylated coumarins by the neutrophil myeloperoxidase produced highly reactive coumarin radical intermediates, which mediated the prooxidant effect observed in the luminol-enhanced chemiluminescence assay.	Coumarins	30-39	myeloperoxidase	Homo sapiens	58-73
23679955-4	2013	Among the 7-unsubstituted coumarins selective, competitive GPR55 antagonists were identified, such as 3-(2-hydroxybenzyl)-5-isopropyl-8-methyl-2H-chromen-2-one (12, PSB-SB-489, IC50 = 1.77 muM, pA2 = 0.547 muM).	Coumarins	26-35	G protein-coupled receptor 55	Homo sapiens	59-64
23988409-1	2013	A series of fused coumarins namely 5-oxo-4,5-dihydropyrano[3,2-c]chromenes linked to N-benzylpyridinium scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors.	Coumarins	18-27	acetylcholinesterase (Cartwright blood group)	Homo sapiens	147-167
23988409-1	2013	A series of fused coumarins namely 5-oxo-4,5-dihydropyrano[3,2-c]chromenes linked to N-benzylpyridinium scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors.	Coumarins	18-27	acetylcholinesterase (Cartwright blood group)	Homo sapiens	169-173
23988409-1	2013	A series of fused coumarins namely 5-oxo-4,5-dihydropyrano[3,2-c]chromenes linked to N-benzylpyridinium scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors.	Coumarins	18-27	butyrylcholinesterase	Homo sapiens	179-200
23988409-1	2013	A series of fused coumarins namely 5-oxo-4,5-dihydropyrano[3,2-c]chromenes linked to N-benzylpyridinium scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors.	Coumarins	18-27	butyrylcholinesterase	Homo sapiens	202-207
23072555-4	2013	The phenylcarbamate substituted coumarins (4a-4h) demonstrated more potent AChE inhibitory as compared to parent 7-hydroxy-4-methylcoumarin.	Coumarins	32-41	acetylcholinesterase	Rattus norvegicus	75-79
23679955-4	2013	Among the 7-unsubstituted coumarins selective, competitive GPR55 antagonists were identified, such as 3-(2-hydroxybenzyl)-5-isopropyl-8-methyl-2H-chromen-2-one (12, PSB-SB-489, IC50 = 1.77 muM, pA2 = 0.547 muM).	Coumarins	26-35	latexin	Homo sapiens	189-192
23679955-4	2013	Among the 7-unsubstituted coumarins selective, competitive GPR55 antagonists were identified, such as 3-(2-hydroxybenzyl)-5-isopropyl-8-methyl-2H-chromen-2-one (12, PSB-SB-489, IC50 = 1.77 muM, pA2 = 0.547 muM).	Coumarins	26-35	latexin	Homo sapiens	206-209
22299576-5	2013	These coumarins thus act as isoform-selective CA inhibitors with the possibility to target isoforms involved in pathologies such as obesity (CA VA/VB) or cancer (CA IX and XII) without inhibiting the physiologically dominant, highly abundant hCA I and II.	Coumarins	6-15	carbonic anhydrase 5A	Homo sapiens	141-146
22299576-5	2013	These coumarins thus act as isoform-selective CA inhibitors with the possibility to target isoforms involved in pathologies such as obesity (CA VA/VB) or cancer (CA IX and XII) without inhibiting the physiologically dominant, highly abundant hCA I and II.	Coumarins	6-15	carbonic anhydrase 9	Homo sapiens	162-167
22299576-5	2013	These coumarins thus act as isoform-selective CA inhibitors with the possibility to target isoforms involved in pathologies such as obesity (CA VA/VB) or cancer (CA IX and XII) without inhibiting the physiologically dominant, highly abundant hCA I and II.	Coumarins	6-15	cytochrome P450 family 24 subfamily A member 1	Homo sapiens	242-254
23387899-3	2013	Among novel chemotypes, coumarins and their congeners were shown to be potent and selective hCA IX inhibitors (CAI) in vitro with an alternative mechanism of action in respect to sulfonamide-based inhibitors.	Coumarins	24-33	carbonic anhydrase 9	Homo sapiens	92-98
23931437-7	2013	2) Coumarins, flavonoids, stilbenes, and other natural products are also important AChE inhibitors from natural products.	Coumarins	3-12	acetylcholinesterase (Cartwright blood group)	Homo sapiens	83-87
23377187-6	2013	This is the first report demonstrating that coumarins inhibit viral replication through an IFN-mediated anti-viral response.	Coumarins	44-53	interferon alpha 1	Homo sapiens	91-94
23199483-4	2013	The search for specific CA IX inhibitors by using the sugar approach has become an important research field, leading to sulfonamides, sulfamates, sulfamides and coumarins with excellent in vitro activity and relevant potency in vivo, in animal models of cancer.	Coumarins	161-170	carbonic anhydrase 9	Homo sapiens	24-29
23340441-0	2013	Total coumarins from Urtica dentata Hand prevent murine autoimmune diabetes via suppression of the TLR4-signaling pathways.	Coumarins	6-15	toll-like receptor 4	Mus musculus	99-103
22257528-0	2012	A review on coumarins as acetylcholinesterase inhibitors for Alzheimer"s disease.	Coumarins	12-21	acetylcholinesterase (Cartwright blood group)	Homo sapiens	25-45
23111986-2	2012	The present study introduces new 3-heteroaryl coumarins decorated with a primary phosphate group (OP(O)(OH)(2)) attached to C-4 in 2,2,4-trimethyl-1,2-dihydroquinoline fragment fused with the coumarin fluorophore.	Coumarins	46-55	complement C4A (Rodgers blood group)	Homo sapiens	124-127
23387854-1	2012	In this study, zinc (0 to 1500 muM) and cadmium ions (0 to 100 muM) were tested as potential elicitors of the production of coumarins in angelica cell suspension cultures.	Coumarins	124-133	latexin	Homo sapiens	63-66
22524172-4	2012	Following intestinal absorption, coumarins inhibit multiple steps of the clotting cascade that leads to inhibition of coagulation factors II, VII, IX and X.	Coumarins	33-42	coagulation factor II, thrombin	Homo sapiens	118-155
22473938-7	2012	These SAR studies, which were expanded to include the permethylated lamellarin derivative (17) and a series of lamellarin-inspired synthetic coumarins (19-24) and isoquinolines (25-26), successfully revealed 17 as a promising new non-cytotoxic P-gp inhibitor pharmacophore.	Coumarins	141-150	sarcosine dehydrogenase	Homo sapiens	6-9
22643355-5	2012	Coumarins can modulate TRAIL-mediated apoptosis in cancer cells.	Coumarins	0-9	TNF superfamily member 10	Homo sapiens	23-28
23047230-0	2012	Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors.	Coumarins	47-56	arachidonate 15-lipoxygenase	Homo sapiens	67-82
22439898-6	2012	The mechanism of action of coumarins on urticaria is not known, but may be related to decrease in thrombin production or to interference of activation of other inflammatory proteins produced during the coagulation process.	Coumarins	27-36	coagulation factor II, thrombin	Homo sapiens	98-106
22831798-0	2012	Suppressive effects of coumarins from Mammea siamensis on inducible nitric oxide synthase expression in RAW264.7 cells.	Coumarins	23-32	nitric oxide synthase 2, inducible	Mus musculus	58-89
22264757-0	2012	Substrate specificity of acetoxy derivatives of coumarins and quinolones towards Calreticulin mediated transacetylation: investigations on antiplatelet function.	Coumarins	48-57	calreticulin	Homo sapiens	81-93
22257528-2	2012	Coumarins are the phytochemicals with wide range of biological activities including AChE inhibition.	Coumarins	0-9	acetylcholinesterase (Cartwright blood group)	Homo sapiens	84-88
22222157-1	2012	The present study was demonstrated to evaluate the effects of naturally occurring coumarins (NOCs) including simple coumarins, furanocoumarins, and pyranocoumarins on the inhibition of beta-secretase (BACE1) activity.	Coumarins	82-91	beta-secretase 1	Homo sapiens	201-206
22222157-1	2012	The present study was demonstrated to evaluate the effects of naturally occurring coumarins (NOCs) including simple coumarins, furanocoumarins, and pyranocoumarins on the inhibition of beta-secretase (BACE1) activity.	Coumarins	116-125	beta-secretase 1	Homo sapiens	201-206
22222157-2	2012	Of 41 NOCs examined, some furanocoumarins inhibited BACE1 activity, but simple coumarins and pyranocoumarins did not affect.	Coumarins	32-41	beta-secretase 1	Homo sapiens	52-57
22222157-6	2012	The kinetics of inhibition of BACE1 by coumarins 24 was non-competitive inhibitors.	Coumarins	39-48	beta-secretase 1	Homo sapiens	30-35
22001857-6	2011	AIM OF STUDY: To explore effects of total coumarins (TC) isolated from UDH on the development of type II collagen (CII)-induced arthritis (CIA) in Balb/c mice.	Coumarins	42-51	nuclear receptor coactivator 5	Mus musculus	139-142
23231391-9	2012	Different families of nitrogen and oxygen heterocycles, such as pyrazoles, hydrazinylthiazoles, xanthones, coumarins or chromones have also been extensively used as scaffolds in medicinal chemistry programs for searching novel MAO-B inhibitors.	Coumarins	107-116	monoamine oxidase B	Homo sapiens	227-232
23231397-4	2012	Differently substituted coumarins have been synthesized and evaluated as MAO-A and MAO-B inhibitors.	Coumarins	24-33	monoamine oxidase A	Homo sapiens	73-78
23231397-4	2012	Differently substituted coumarins have been synthesized and evaluated as MAO-A and MAO-B inhibitors.	Coumarins	24-33	monoamine oxidase B	Homo sapiens	83-88
23231398-7	2012	For this reason, multiple scaffolds, such as substituted coumarins, indolylmethylamine or pyridazine derivatives were synthesized and assayed toward MAO-A and MAO-B inhibition.	Coumarins	57-66	monoamine oxidase A	Homo sapiens	149-154
22493800-4	2012	This review is focused on the natural compounds that exhibit the aromatase inhibition, which include flavonoids, xanthones, coumarins, and sesquiterpenes.	Coumarins	124-133	cytochrome P450 family 19 subfamily A member 1	Homo sapiens	65-74
22077347-2	2011	These coumarins were very weak or ineffective as inhibitors of the housekeeping, off target isoforms CA I and II, but some of them inhibited tumor-associated CA IX and XII in the low nanomolar range.	Coumarins	6-15	carbonic anhydrase 1	Mus musculus	101-105
22077347-2	2011	These coumarins were very weak or ineffective as inhibitors of the housekeeping, off target isoforms CA I and II, but some of them inhibited tumor-associated CA IX and XII in the low nanomolar range.	Coumarins	6-15	carbonic anhydrase 9	Mus musculus	158-163
21343376-10	2011	Coumarins, quinolones, antiepileptics, and hydrochlorothiazide were frequently part of a PDI.	Coumarins	0-9	peptidyl arginine deiminase 1	Homo sapiens	89-92
21651319-1	2011	BACKGROUND: Polymorphisms in the genes encoding the cytochrome P450 2C9 enzyme (CYP2C9) and the vitamin K epoxide reductase (VKORC1) are known to contribute to variability in sensitivity to coumarins.	Coumarins	190-199	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	52-71
21651319-1	2011	BACKGROUND: Polymorphisms in the genes encoding the cytochrome P450 2C9 enzyme (CYP2C9) and the vitamin K epoxide reductase (VKORC1) are known to contribute to variability in sensitivity to coumarins.	Coumarins	190-199	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	80-86
21651319-1	2011	BACKGROUND: Polymorphisms in the genes encoding the cytochrome P450 2C9 enzyme (CYP2C9) and the vitamin K epoxide reductase (VKORC1) are known to contribute to variability in sensitivity to coumarins.	Coumarins	190-199	vitamin K epoxide reductase complex subunit 1	Homo sapiens	96-123
21651319-1	2011	BACKGROUND: Polymorphisms in the genes encoding the cytochrome P450 2C9 enzyme (CYP2C9) and the vitamin K epoxide reductase (VKORC1) are known to contribute to variability in sensitivity to coumarins.	Coumarins	190-199	vitamin K epoxide reductase complex subunit 1	Homo sapiens	125-131
21991256-4	2011	The present study was designed to determine the activity of these coumarine compounds on CFTR activity in animal tissues as a primary evaluation of their therapeutic potential.	Coumarins	66-75	CF transmembrane conductance regulator	Rattus norvegicus	89-93
21688820-1	2011	An intermolecular cycloaddition reaction has been developed, where o-arylcarboxybenzonitriles react with alkynes to afford coumarins in the presence of Ni(0)/P(CH(2)Ph)(3)/MAD as a catalyst.	Coumarins	123-132	MAX dimerization protein 1	Homo sapiens	172-175
21620826-9	2011	Regulation of mABCG2 by cortex fraxini coumarines may be partly contributed to their beneficial actions.	Coumarins	39-49	ATP binding cassette subfamily G member 2 (Junior blood group)	Mus musculus	14-20
21214226-1	2011	In an effort to identify natural product-based molecular-targeted antitumor agents, mammea-type coumarins from the tropical/subtropical plant Mammea americana were found to inhibit the activation of HIF-1 (hypoxia-inducible factor-1) in human breast and prostate tumor cells.	Coumarins	96-105	hypoxia inducible factor 1 subunit alpha	Homo sapiens	199-204
21316817-5	2011	According to our results, docking experiments could be an interesting approach to try to predict the activity of this class of coumarins against MAO-B receptors.	Coumarins	127-136	monoamine oxidase B	Homo sapiens	145-150
21185922-0	2011	Hepatoprotective and TNF-alpha inhibitory activity of Zosima absinthifolia extracts and coumarins.	Coumarins	88-97	tumor necrosis factor	Rattus norvegicus	21-30
21031633-2	2011	Many biological features of this genus such as cytotoxicity, antibacterial, antiviral, P-glycoprotein (P-gp) inhibitory and antiinflammatory activity have been attributed to sesquiterpene coumarins; structures containing a common coumarin group and a sesquiterpene moiety.	Coumarins	188-197	ATP binding cassette subfamily B member 1	Homo sapiens	87-101
21031633-2	2011	Many biological features of this genus such as cytotoxicity, antibacterial, antiviral, P-glycoprotein (P-gp) inhibitory and antiinflammatory activity have been attributed to sesquiterpene coumarins; structures containing a common coumarin group and a sesquiterpene moiety.	Coumarins	188-197	ATP binding cassette subfamily B member 1	Homo sapiens	103-107
21214226-6	2011	Coumarins possessing a 6-prenyl-8-(3-methyloxobutyl) substituent pattern exhibited enhanced HIF-1 inhibitory effects.	Coumarins	0-9	hypoxia inducible factor 1 subunit alpha	Homo sapiens	92-97
20580555-2	2010	These coumarins were very weak or ineffective as inhibitors of the house-keeping, offtarget isoforms CA I and II, but showed effective, submicromolar inhibition of the transmembrane, tumor-associated isoforms CA IX and XII.	Coumarins	6-15	carbonic anhydrase 1	Homo sapiens	101-105
21138273-3	2011	We have discovered that simple coumarines 1 and 2 significantly inhibit 17beta-HSD1 in a recombinant enzyme assay, with high selectivity against 17beta-HSD2.	Coumarins	31-41	hydroxysteroid 17-beta dehydrogenase 1	Homo sapiens	72-83
21138273-3	2011	We have discovered that simple coumarines 1 and 2 significantly inhibit 17beta-HSD1 in a recombinant enzyme assay, with high selectivity against 17beta-HSD2.	Coumarins	31-41	hydroxysteroid 17-beta dehydrogenase 2	Homo sapiens	145-156
22615634-2	2011	Coumarins have been shown at concentrations inhibiting phospoliphase C-Y (Phc-Y) are able to enhance tight junction (TJ) permeability due to hyperpoalation of Zonolous Occludense-1 (ZO-1) proteins.	Coumarins	0-9	tight junction protein 1	Rattus norvegicus	159-186
21067924-2	2010	All these coumarins were very weak or ineffective as inhibitors of the housekeeping, offtarget isoforms CA I and II.	Coumarins	10-19	carbonic anhydrase 1	Homo sapiens	104-108
20677317-1	2010	A large series of substituted coumarins linked through an appropriate spacer to 3-hydroxy-N,N-dimethylanilino or 3-hydroxy-N,N,N-trialkylbenzaminium moieties were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors.	Coumarins	30-39	acetylcholinesterase (Cartwright blood group)	Homo sapiens	192-212
20677317-1	2010	A large series of substituted coumarins linked through an appropriate spacer to 3-hydroxy-N,N-dimethylanilino or 3-hydroxy-N,N,N-trialkylbenzaminium moieties were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors.	Coumarins	30-39	acetylcholinesterase (Cartwright blood group)	Homo sapiens	214-218
20677317-1	2010	A large series of substituted coumarins linked through an appropriate spacer to 3-hydroxy-N,N-dimethylanilino or 3-hydroxy-N,N,N-trialkylbenzaminium moieties were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors.	Coumarins	30-39	butyrylcholinesterase	Homo sapiens	224-245
20677317-1	2010	A large series of substituted coumarins linked through an appropriate spacer to 3-hydroxy-N,N-dimethylanilino or 3-hydroxy-N,N,N-trialkylbenzaminium moieties were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors.	Coumarins	30-39	butyrylcholinesterase	Homo sapiens	247-251
21469766-1	2011	BACKGROUND: Variant alleles of vitamin K epoxide reductase complex subunit 1 gene (VKORC1), the target molecule of vitamin K antagonists, and of cytochrome P450 (CYP) 2C9, an enzyme involved in coumarin metabolism, affect the anticoagulant response of coumarins, which have a narrow therapeutic window.	Coumarins	252-261	vitamin K epoxide reductase complex subunit 1	Homo sapiens	31-76
21469766-1	2011	BACKGROUND: Variant alleles of vitamin K epoxide reductase complex subunit 1 gene (VKORC1), the target molecule of vitamin K antagonists, and of cytochrome P450 (CYP) 2C9, an enzyme involved in coumarin metabolism, affect the anticoagulant response of coumarins, which have a narrow therapeutic window.	Coumarins	252-261	vitamin K epoxide reductase complex subunit 1	Homo sapiens	83-89
21469766-1	2011	BACKGROUND: Variant alleles of vitamin K epoxide reductase complex subunit 1 gene (VKORC1), the target molecule of vitamin K antagonists, and of cytochrome P450 (CYP) 2C9, an enzyme involved in coumarin metabolism, affect the anticoagulant response of coumarins, which have a narrow therapeutic window.	Coumarins	252-261	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	145-170
20580555-2	2010	These coumarins were very weak or ineffective as inhibitors of the house-keeping, offtarget isoforms CA I and II, but showed effective, submicromolar inhibition of the transmembrane, tumor-associated isoforms CA IX and XII.	Coumarins	6-15	carbonic anhydrase 9	Homo sapiens	209-214
19954971-0	2010	Coumarins as novel 17beta-hydroxysteroid dehydrogenase type 3 inhibitors for potential treatment of prostate cancer.	Coumarins	0-9	hydroxysteroid 17-beta dehydrogenase 3	Homo sapiens	19-61
20585445-1	2010	The identification of CYP2C9 and VKORC1 genes has strongly stimulated the research on pharmacogenetics of coumarins in the last decade.	Coumarins	106-115	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	22-28
20585445-1	2010	The identification of CYP2C9 and VKORC1 genes has strongly stimulated the research on pharmacogenetics of coumarins in the last decade.	Coumarins	106-115	vitamin K epoxide reductase complex subunit 1	Homo sapiens	33-39
20024333-1	2010	Cucurbit[8]uril (as low as 10 mol%) acts as a supramolecular catalytic nanoreaction vessel and facilitates the photodimerization of coumarins in water leading to syn dimers.	Coumarins	132-141	synemin	Homo sapiens	162-165
20354170-8	2010	We conclude that long-term use of coumarins is associated with enhanced extracoronary vascular calcification, possibly through the inhibition of MGP carboxylation.	Coumarins	34-43	matrix Gla protein	Homo sapiens	145-148
20121287-2	2010	OBJECTIVE: We hypothesized that in patients treated with coumarins, alveolar hemorrhage is associated with vitamin K epoxide reductase (VKORC1) and cytochrome P450 (CYP) 2C9 (CYP2C9) variant alleles.	Coumarins	57-66	vitamin K epoxide reductase complex subunit 1	Homo sapiens	107-134
20121287-2	2010	OBJECTIVE: We hypothesized that in patients treated with coumarins, alveolar hemorrhage is associated with vitamin K epoxide reductase (VKORC1) and cytochrome P450 (CYP) 2C9 (CYP2C9) variant alleles.	Coumarins	57-66	vitamin K epoxide reductase complex subunit 1	Homo sapiens	136-142
20121287-2	2010	OBJECTIVE: We hypothesized that in patients treated with coumarins, alveolar hemorrhage is associated with vitamin K epoxide reductase (VKORC1) and cytochrome P450 (CYP) 2C9 (CYP2C9) variant alleles.	Coumarins	57-66	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	148-173
20121287-2	2010	OBJECTIVE: We hypothesized that in patients treated with coumarins, alveolar hemorrhage is associated with vitamin K epoxide reductase (VKORC1) and cytochrome P450 (CYP) 2C9 (CYP2C9) variant alleles.	Coumarins	57-66	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	175-181
19577453-5	2010	In reporter gene assay, the two coumarins (10(-8)-10(-5)M) acted as ERalpha-selective agonists while the other compounds (10(-9)-10(-6)M) activated both ERalpha and ERbeta.	Coumarins	32-41	estrogen receptor 1	Homo sapiens	68-75
19577453-5	2010	In reporter gene assay, the two coumarins (10(-8)-10(-5)M) acted as ERalpha-selective agonists while the other compounds (10(-9)-10(-6)M) activated both ERalpha and ERbeta.	Coumarins	32-41	estrogen receptor 1	Homo sapiens	153-160
19883715-5	2010	Three coumarins and 12 flavonoids significantly suppressed CYP3A4 or CYP2C9 activities.	Coumarins	6-15	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	69-75
19918833-6	2010	Molecular modeling studies based on the X-ray crystal structures of both human caspases 3 and 8 revealed that there is sufficient room within both active sites to accommodate substrates with moderately bulky substituents in the 3- and 4-positions of the fluorogenic coumarins and quinolin-2(1H)-ones.	Coumarins	266-275	caspase 8	Homo sapiens	79-87
20205664-1	2010	The identification of the genes encoding CYP2C9, the principal metabolizing enzyme of the coumarins, and VKORC1, the molecular target for coumarins, has strongly stimulated the research on pharmacogenetics of vitamin K antagonists, also designated as coumarins.	Coumarins	90-99	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	41-47
20205664-1	2010	The identification of the genes encoding CYP2C9, the principal metabolizing enzyme of the coumarins, and VKORC1, the molecular target for coumarins, has strongly stimulated the research on pharmacogenetics of vitamin K antagonists, also designated as coumarins.	Coumarins	138-147	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	41-47
20205664-1	2010	The identification of the genes encoding CYP2C9, the principal metabolizing enzyme of the coumarins, and VKORC1, the molecular target for coumarins, has strongly stimulated the research on pharmacogenetics of vitamin K antagonists, also designated as coumarins.	Coumarins	138-147	vitamin K epoxide reductase complex subunit 1	Homo sapiens	105-111
20205664-1	2010	The identification of the genes encoding CYP2C9, the principal metabolizing enzyme of the coumarins, and VKORC1, the molecular target for coumarins, has strongly stimulated the research on pharmacogenetics of vitamin K antagonists, also designated as coumarins.	Coumarins	138-147	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	41-47
20205664-1	2010	The identification of the genes encoding CYP2C9, the principal metabolizing enzyme of the coumarins, and VKORC1, the molecular target for coumarins, has strongly stimulated the research on pharmacogenetics of vitamin K antagonists, also designated as coumarins.	Coumarins	138-147	vitamin K epoxide reductase complex subunit 1	Homo sapiens	105-111
19397481-5	2009	Growing evidence indicates that up to 60% of the individual pharmacological response to coumarins might be due to genetic variables and affected by polymorphisms in the genes encoding two enzymes, namely, vitamin K epoxide reductase (VKOR) and cytochrome P450 CYP2C9.	Coumarins	88-97	vitamin K epoxide reductase complex subunit 1	Homo sapiens	205-232
19200363-7	2009	The mechanism(s) of how mutations in the VKORC1 gene mediate insensitivity to coumarins in vivo has still to be elucidated.	Coumarins	78-87	vitamin K epoxide reductase complex, subunit 1	Rattus norvegicus	41-47
22461099-8	2009	However, only variations in VKORC1 and CYP2C9 have consistently been associated with drug response (coumarins) and have clinical implications.	Coumarins	100-109	vitamin K epoxide reductase complex subunit 1	Homo sapiens	28-34
19689106-0	2009	Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4.	Coumarins	12-21	cytochrome P450 family 3 subfamily A member 4	Homo sapiens	82-101
19799531-7	2009	The second enzyme that is involved in coumarins metabolism is the vitamin K epoxide reductase (VKORC).	Coumarins	38-47	vitamin K epoxide reductase complex subunit 1	Homo sapiens	66-93
19150646-1	2009	Naturally occurring coumarins possess anti-carcinogenic activities in part by inducing carcinogen-detoxifying enzymes glutathione S-transferase (GST) and/or NAD(P)H quinone oxidoreductase (NQO1).	Coumarins	20-29	hematopoietic prostaglandin D synthase	Mus musculus	118-143
19150646-1	2009	Naturally occurring coumarins possess anti-carcinogenic activities in part by inducing carcinogen-detoxifying enzymes glutathione S-transferase (GST) and/or NAD(P)H quinone oxidoreductase (NQO1).	Coumarins	20-29	hematopoietic prostaglandin D synthase	Mus musculus	145-148
19150646-1	2009	Naturally occurring coumarins possess anti-carcinogenic activities in part by inducing carcinogen-detoxifying enzymes glutathione S-transferase (GST) and/or NAD(P)H quinone oxidoreductase (NQO1).	Coumarins	20-29	NAD(P)H dehydrogenase, quinone 1	Mus musculus	189-193
19150646-2	2009	Our goal was to determine whether citrus coumarins induce hepatic GST and/or NQO1 via activation of Nrf2 and the antioxidant response element (ARE).	Coumarins	41-50	hematopoietic prostaglandin D synthase	Mus musculus	66-69
19150646-2	2009	Our goal was to determine whether citrus coumarins induce hepatic GST and/or NQO1 via activation of Nrf2 and the antioxidant response element (ARE).	Coumarins	41-50	NAD(P)H dehydrogenase, quinone 1	Mus musculus	77-81
19150646-2	2009	Our goal was to determine whether citrus coumarins induce hepatic GST and/or NQO1 via activation of Nrf2 and the antioxidant response element (ARE).	Coumarins	41-50	nuclear factor, erythroid derived 2, like 2	Mus musculus	100-104
19056347-0	2009	Crystal structures of rat catechol-O-methyltransferase complexed with coumarine-based inhibitor.	Coumarins	70-79	catechol-O-methyltransferase	Rattus norvegicus	26-54
19738376-5	2009	METHODS: We established a polymerase chain reaction technique for rapid genotyping of the vitamin K epoxide reductase complex (VKORC1), which is the pharmaceutical target of the coumarins.	Coumarins	178-187	vitamin K epoxide reductase complex subunit 1	Homo sapiens	127-133
22461099-8	2009	However, only variations in VKORC1 and CYP2C9 have consistently been associated with drug response (coumarins) and have clinical implications.	Coumarins	100-109	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	39-45
19397481-5	2009	Growing evidence indicates that up to 60% of the individual pharmacological response to coumarins might be due to genetic variables and affected by polymorphisms in the genes encoding two enzymes, namely, vitamin K epoxide reductase (VKOR) and cytochrome P450 CYP2C9.	Coumarins	88-97	vitamin K epoxide reductase complex subunit 1	Homo sapiens	234-238
19397481-5	2009	Growing evidence indicates that up to 60% of the individual pharmacological response to coumarins might be due to genetic variables and affected by polymorphisms in the genes encoding two enzymes, namely, vitamin K epoxide reductase (VKOR) and cytochrome P450 CYP2C9.	Coumarins	88-97	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	260-266
18637681-1	2008	In order to explore the inhibitory mechanism of coumarins toward aldose reductase (ALR2), AutoDock and Gromacs software were used for docking and molecular dynamics studies on 14 coumarins (CM) and ALR2 protease.	Coumarins	179-188	aldo-keto reductase family 1 member B	Homo sapiens	65-81
18778776-0	2008	Inhibition of acetylcholinesterase by coumarins: the case of coumarin 106.	Coumarins	38-47	acetylcholinesterase (Cartwright blood group)	Homo sapiens	14-34
18637681-0	2008	Docking and molecular dynamics study on the inhibitory activity of coumarins on aldose reductase.	Coumarins	67-76	aldo-keto reductase family 1 member B	Homo sapiens	80-96
18637681-1	2008	In order to explore the inhibitory mechanism of coumarins toward aldose reductase (ALR2), AutoDock and Gromacs software were used for docking and molecular dynamics studies on 14 coumarins (CM) and ALR2 protease.	Coumarins	48-57	aldo-keto reductase family 1 member B	Homo sapiens	65-81
18637681-1	2008	In order to explore the inhibitory mechanism of coumarins toward aldose reductase (ALR2), AutoDock and Gromacs software were used for docking and molecular dynamics studies on 14 coumarins (CM) and ALR2 protease.	Coumarins	48-57	aldo-keto reductase family 1 member B	Homo sapiens	83-87
19275614-10	2009	Some oxygen heterocycles, coumarines and chromenes, have also drawn attention as MIF inhibitors.	Coumarins	26-36	macrophage migration inhibitory factor	Homo sapiens	81-84
18805772-2	2008	Vitamin K epoxide reductase (VKORC1) is the site of inhibition by coumarins.	Coumarins	66-75	vitamin K epoxide reductase complex subunit 1	Homo sapiens	0-27
18805772-2	2008	Vitamin K epoxide reductase (VKORC1) is the site of inhibition by coumarins.	Coumarins	66-75	vitamin K epoxide reductase complex subunit 1	Homo sapiens	29-35
18637681-1	2008	In order to explore the inhibitory mechanism of coumarins toward aldose reductase (ALR2), AutoDock and Gromacs software were used for docking and molecular dynamics studies on 14 coumarins (CM) and ALR2 protease.	Coumarins	48-57	aldo-keto reductase family 1 member B	Homo sapiens	198-202
18637681-1	2008	In order to explore the inhibitory mechanism of coumarins toward aldose reductase (ALR2), AutoDock and Gromacs software were used for docking and molecular dynamics studies on 14 coumarins (CM) and ALR2 protease.	Coumarins	179-188	aldo-keto reductase family 1 member B	Homo sapiens	83-87
18304811-0	2008	Synthesis and biological activity of simplified denoviose-coumarins related to novobiocin as potent inhibitors of heat-shock protein 90 (hsp90).	Coumarins	58-67	heat shock protein 90 alpha family class A member 1	Homo sapiens	114-135
18304811-0	2008	Synthesis and biological activity of simplified denoviose-coumarins related to novobiocin as potent inhibitors of heat-shock protein 90 (hsp90).	Coumarins	58-67	heat shock protein 90 alpha family class A member 1	Homo sapiens	137-142
17868161-5	2007	Most of the compounds were found to be moderately active, however, one potent and subtype selective mGluR1 antagonist, 13 (IC(50): 0.362 microM, SEM +/-0.031; K(i): 0.753 microM, SEM +/-0.048), based on a coumarine scaffold was discovered.	Coumarins	205-214	glutamate metabotropic receptor 1	Homo sapiens	100-106
17979263-5	2007	Removal of the noviose moiety in novobiocin together with introduction of a tosyl substituent at C-4 or C-7 coumarins provides 6e and 6f as lead structures which compared favorably with novobiocin as demonstrated by enhanced rates of cell death.	Coumarins	108-117	complement C7	Homo sapiens	104-107
18278162-2	2008	VKORC1 protein is targeted by Coumarins.	Coumarins	30-39	vitamin K epoxide reductase complex subunit 1	Homo sapiens	0-6