PMID-sentid	Pub_year	Sent_text	compound_name	comp_offset	prot_official_name	organism	prot_offset
16822479-6	2006	Here, we present data to show that both 4-OH and 4"-OH are critical for the ability of 4,4"-DHS to induce down-regulation of ERalpha and suggest that 4,4"-DHS provides a useful scaffold for development of novel ERalpha antagonists.	4-oh	40-44	estrogen receptor 1	Homo sapiens	125-132
18156313-10	2008	We provide evidence that CYP2C enzymes, which were found to be up-regulated in Cyp3a knockout mice, are primarily responsible for this metabolism and that several but not all murine CYP2C enzymes are capable of metabolizing midazolam to its 1"-OH and/or 4-OH derivatives.	4-oh	254-258	cytochrome P450, family 2, subfamily c, polypeptide 29	Mus musculus	25-30
18156313-10	2008	We provide evidence that CYP2C enzymes, which were found to be up-regulated in Cyp3a knockout mice, are primarily responsible for this metabolism and that several but not all murine CYP2C enzymes are capable of metabolizing midazolam to its 1"-OH and/or 4-OH derivatives.	4-oh	254-258	cytochrome P450, family 3, subfamily a, polypeptide 11	Mus musculus	79-84
17256924-4	2007	Concentration-dependent, PLAP-mediated conversion of IQ2-P,4-P (4)/125IQ2-P,4-P (6) to water-insoluble 2-(2",4"-dihydroxyphenyl)-6-[127I/125I]iodo-4-(3H)-quinazolinone (127IQ2-OH,4-OH (2)/125IQ2-OH,4-OH (7)) was observed in solution.	4-oh	179-183	alkaline phosphatase, placental	Homo sapiens	25-29
17256924-4	2007	Concentration-dependent, PLAP-mediated conversion of IQ2-P,4-P (4)/125IQ2-P,4-P (6) to water-insoluble 2-(2",4"-dihydroxyphenyl)-6-[127I/125I]iodo-4-(3H)-quinazolinone (127IQ2-OH,4-OH (2)/125IQ2-OH,4-OH (7)) was observed in solution.	4-oh	198-202	alkaline phosphatase, placental	Homo sapiens	25-29
16328061-8	2006	After treatment with 4-OH tamoxifen, down-regulation of basal MT1 receptor expression in ERalpha-positive MCF-7 cells and inhibition of melatonin-induced up-regulation of MT1 in OVCAR-3 ovarian cancer cells were observed.	4-oh	21-25	metallothionein 1I, pseudogene	Homo sapiens	62-65
16509590-6	2006	A collection of analytically defined lipolanthionine peptide amides exhibited an inhibitory effect of the TLR2-mediated IL-8 secretion when applied in high molar excess to the agonistic synthetic lipopeptide Pam3Cys-Ser-(Lys)4-OH.	4-oh	225-229	toll like receptor 2	Homo sapiens	106-110
16509590-6	2006	A collection of analytically defined lipolanthionine peptide amides exhibited an inhibitory effect of the TLR2-mediated IL-8 secretion when applied in high molar excess to the agonistic synthetic lipopeptide Pam3Cys-Ser-(Lys)4-OH.	4-oh	225-229	C-X-C motif chemokine ligand 8	Homo sapiens	120-124
16328061-8	2006	After treatment with 4-OH tamoxifen, down-regulation of basal MT1 receptor expression in ERalpha-positive MCF-7 cells and inhibition of melatonin-induced up-regulation of MT1 in OVCAR-3 ovarian cancer cells were observed.	4-oh	21-25	metallothionein 1I, pseudogene	Homo sapiens	171-174
16328061-9	2006	In contrast, treatment with 4-OH tamoxifen increased the MT1 receptor level in ERalpha-negative SK-OV-3 ovarian cancer cells.	4-oh	28-32	metallothionein 1I, pseudogene	Homo sapiens	57-60
12855564-5	2003	Treatment of DCs with 4-OH-IF significantly reduced their ability to stimulate allogeneic T-cell proliferation and interferon-gamma (IFN-gamma) production.	4-oh	22-26	interferon gamma	Homo sapiens	115-131
15502008-7	2005	UGT1A8 was most active toward the 1-OH, 4-OH, 5-OH, 6-OH, 7-OH, 10-OH, 11-OH, and 12-OH derivatives of benzo[a]pyrene.	4-oh	40-44	UDP glucuronosyltransferase family 1 member A8	Rattus norvegicus	0-6
12855564-5	2003	Treatment of DCs with 4-OH-IF significantly reduced their ability to stimulate allogeneic T-cell proliferation and interferon-gamma (IFN-gamma) production.	4-oh	22-26	interferon gamma	Homo sapiens	133-142
8886602-1	1996	Midazolam (MDZ) is metabolized in human liver microsomes by the cytochrome P450 (CYP) 3A subfamily to 1"-hydroxy (1"-OH) and 4-hydroxy (4-OH) metabolites.	4-oh	136-140	cytochrome P450 family 4 subfamily F member 3	Homo sapiens	64-79
14553828-5	2003	In CM and CF, 4-OH tamoxifen and ICI 182,780 treatment reduced proliferating cell nuclear antigen protein expression and concomitantly increased p27Kip1.	4-oh	14-18	cyclin-dependent kinase inhibitor 1B	Rattus norvegicus	145-152
14553828-6	2003	4-OH Tamoxifen and ICI 182,780 treatment increased ERK1/2 phosphorylation in CM and CF, and ERK1/2 kinase (MEK)-dependent inhibition of ERK1/2 activation attenuated ICI 182,780-mediated suppression of DNA synthesis.	4-oh	0-4	mitogen activated protein kinase 3	Rattus norvegicus	51-57
14553828-6	2003	4-OH Tamoxifen and ICI 182,780 treatment increased ERK1/2 phosphorylation in CM and CF, and ERK1/2 kinase (MEK)-dependent inhibition of ERK1/2 activation attenuated ICI 182,780-mediated suppression of DNA synthesis.	4-oh	0-4	mitogen activated protein kinase 3	Rattus norvegicus	92-98
14553828-6	2003	4-OH Tamoxifen and ICI 182,780 treatment increased ERK1/2 phosphorylation in CM and CF, and ERK1/2 kinase (MEK)-dependent inhibition of ERK1/2 activation attenuated ICI 182,780-mediated suppression of DNA synthesis.	4-oh	0-4	mitogen activated protein kinase 3	Rattus norvegicus	92-98
12814972-3	2003	Recombinant CYP3A4 and CYP3A5 (rCYP3A4 and rCYP3A5) both produced 1-OH and 4-OH metabolites from midazolam and triazolam, 6 beta-hydroxytestosterone from testosterone, and oxidized nifedipine from nifedipine.	4-oh	75-79	cytochrome P450 family 3 subfamily A member 4	Homo sapiens	12-18
12814972-3	2003	Recombinant CYP3A4 and CYP3A5 (rCYP3A4 and rCYP3A5) both produced 1-OH and 4-OH metabolites from midazolam and triazolam, 6 beta-hydroxytestosterone from testosterone, and oxidized nifedipine from nifedipine.	4-oh	75-79	cytochrome P450 family 3 subfamily A member 5	Homo sapiens	23-29
11922395-5	2002	Cell surface MUC1 expression was determined by flow cytometry in the presence or absence of oestradiol, medroxy progesterone acetate or R1881, with and without 4 hydroxy-flutamide (4-OH), a nonsteroidal AR antagonist.	4-oh	181-185	mucin 1, cell surface associated	Homo sapiens	13-17
10823918-6	2000	Transiently transfected P450RAI-2 can convert all-trans-RA to more polar metabolites including 4-oxo-, 4-OH-, and 18-OH-all-trans-RA.	4-oh	103-107	cytochrome P450 family 26 subfamily B member 1	Homo sapiens	24-33
10076999-6	1999	Additionally, this 4-OH-Tam agonist activity via ERbeta was completely blocked by estrogen.	4-oh	19-23	estrogen receptor 2	Homo sapiens	49-55
9657280-2	1998	In intact mouse liver, pyrazole (PYR) and 4-hydroxypyrazole (4-OH) induce selectively the expression of CYP2A5 while expression of other CYPs is decreased.	4-oh	61-65	cytochrome P450, family 2, subfamily a, polypeptide 5	Mus musculus	104-110
9657280-6	1998	CYP2B9/10-mediated pentoxyresorufin O-deethylase activity (PROD) was decreased by 80% by 4-Me and 4-1, and by 50% by 4-OH while PYR had no marked effect.	4-oh	117-121	cytochrome P450, family 2, subfamily b, polypeptide 9	Mus musculus	0-6
9657280-9	1998	Cimetidine prevented the induction of coumarin 7-hydroxylase activity by PYR and 4-OH by 46 and 74%, respectively indicating that their effects on the expression of CYP2A5 are, at least partly, mediated via their metabolites.	4-oh	81-85	cytochrome P450, family 2, subfamily a, polypeptide 5	Mus musculus	38-60
9657280-9	1998	Cimetidine prevented the induction of coumarin 7-hydroxylase activity by PYR and 4-OH by 46 and 74%, respectively indicating that their effects on the expression of CYP2A5 are, at least partly, mediated via their metabolites.	4-oh	81-85	cytochrome P450, family 2, subfamily a, polypeptide 5	Mus musculus	165-171
2141500-2	1990	Its active metabolite, 4-OH-TAT-59, had a high binding affinity to estrogen receptor (ER), present in the cytosol of the uterus of immature rat, similar to estradiol.	4-oh	23-27	estrogen receptor 1	Rattus norvegicus	67-84
2141500-2	1990	Its active metabolite, 4-OH-TAT-59, had a high binding affinity to estrogen receptor (ER), present in the cytosol of the uterus of immature rat, similar to estradiol.	4-oh	23-27	estrogen receptor 1	Rattus norvegicus	86-88
2820212-3	1987	In fact, chemiluminescence and superoxide anion generation by polymorphonuclear leukocytes (PMN) stimulated with zymosan particles or with the synthetic peptide FMLP are inhibited by nimesulide and its 4-OH metabolite in a dose dependent fashion without affecting cell viability.	4-oh	202-206	formyl peptide receptor 1	Homo sapiens	161-165
35050493-13	2022	The inhibition of TGF-beta expression is a mechanism by which 4-OH TAM suppresses fibroblast growth, preventing capsular formation.	4-oh	62-66	transforming growth factor alpha	Mus musculus	18-26
31585114-8	2019	Metabolite 4-OH clonidine was accurately detected via ultra-performance liquid-chromatography tandem mass spectrometry to evaluate the effect of CYP2D6 genetic polymorphism on the clonidine.	4-oh	11-15	cytochrome P450 family 2 subfamily D member 6	Homo sapiens	145-151
30561249-13	2019	In conclusion, plasma concentrations of 4-OH TRZ, but not those of TRZ and alpha-OH TRZ, might reflect hepatic CYP3A activity in mice in vivo.	4-oh	40-44	cytochrome P450, family 3, subfamily a, polypeptide 11	Mus musculus	111-116
30502134-4	2019	Molecular docking suggests that the first acetylation of phloridzin catalyzed by CALB occurs in 6""-OH, followed by 3""-OH, then 4-OH.	4-oh	129-133	calbindin 1	Homo sapiens	81-85
25737085-4	2015	The SAR study resulted in the novel 2-F, 4-OH derivative (6x) with an IC50 value of 23nM as the highest affinity HCA2 agonist of the biphenyl series, although it showed a similar residence time as nicotinic acid.	4-oh	41-45	MAGE family member C3	Homo sapiens	113-117
27585693-7	2016	Studies characterizing of the 4-OH Tam resistance of MCF7-TamR cells were performed by 17 beta-oestradiol (E2) and Annexin V/PI analysis.	4-oh	30-34	annexin A5	Homo sapiens	115-124
29204052-5	2017	Alterations in CYP3A activity were measured by calculating the kinetic parameters of 4-OH and 1"-OH-midazolam hydroxylation, marker reactions for CYP3A enzymes.	4-oh	85-89	cytochrome P450, family 3, subfamily a, polypeptide 62	Rattus norvegicus	15-20
28533324-4	2017	HuH-7 had less 1-OH MDZ (all P < 0.0005) or 4-OH (all P < 0.005) production in metabolism assays than all bioengineered cell lines.	4-oh	47-51	MIR7-3 host gene	Homo sapiens	0-5
27856237-6	2017	A SAR study of the series revealed that compounds with hydroxyl groups showed better cytotoxicity and TrkA inhibitory potency (in the following order 2,4-OH>2,3,4-OH>3,4-OH>4-OH) than compounds possessing electron donating or withdrawing groups on the benzylidenephenyl ring.	4-oh	152-156	neurotrophic receptor tyrosine kinase 1	Homo sapiens	102-106
27856237-6	2017	A SAR study of the series revealed that compounds with hydroxyl groups showed better cytotoxicity and TrkA inhibitory potency (in the following order 2,4-OH>2,3,4-OH>3,4-OH>4-OH) than compounds possessing electron donating or withdrawing groups on the benzylidenephenyl ring.	4-oh	164-168	neurotrophic receptor tyrosine kinase 1	Homo sapiens	102-106
27856237-6	2017	A SAR study of the series revealed that compounds with hydroxyl groups showed better cytotoxicity and TrkA inhibitory potency (in the following order 2,4-OH>2,3,4-OH>3,4-OH>4-OH) than compounds possessing electron donating or withdrawing groups on the benzylidenephenyl ring.	4-oh	164-168	neurotrophic receptor tyrosine kinase 1	Homo sapiens	102-106
22633008-9	2012	Furthermore, molecular docking and DFT mechanistic studies performed on the rat VKORC1 homology model revealed interactions between the 4-OH coumarin group in the form of phenolic anion and the Cys135 catalytic site in the transition state.	4-oh	136-140	vitamin K epoxide reductase complex, subunit 1	Rattus norvegicus	80-86
24501322-9	2014	Because CYP1A and CYP3A4 metabolize most of the E2 to its noncarcinogenic 2-OH metabolite, and CYP1B1 produces potentially carcinogenic 4-OH metabolite, favorable modulation of these CYPs via systemically delivered curcumin could be one of the potential mechanisms.	4-oh	136-140	cytochrome P450, family 1, subfamily b, polypeptide 1	Rattus norvegicus	95-101
22915089-6	2013	The 4-OH and 4-OH-NDM metabolites of TOR and TAM bound to estrogen receptor (ER) subtypes with fourfold to 30-fold greater affinity were 35- to 187-fold more efficient at antagonizing ER transactivation and had antiestrogenic potency that was up to 360-fold greater than their parent drugs.	4-oh	4-8	estrogen receptor 1	Homo sapiens	58-75
22915089-6	2013	The 4-OH and 4-OH-NDM metabolites of TOR and TAM bound to estrogen receptor (ER) subtypes with fourfold to 30-fold greater affinity were 35- to 187-fold more efficient at antagonizing ER transactivation and had antiestrogenic potency that was up to 360-fold greater than their parent drugs.	4-oh	4-8	estrogen receptor 1	Homo sapiens	77-79
22915089-6	2013	The 4-OH and 4-OH-NDM metabolites of TOR and TAM bound to estrogen receptor (ER) subtypes with fourfold to 30-fold greater affinity were 35- to 187-fold more efficient at antagonizing ER transactivation and had antiestrogenic potency that was up to 360-fold greater than their parent drugs.	4-oh	4-8	estrogen receptor 1	Homo sapiens	184-186
24014653-11	2013	NDL-PCBs and their 5-OH and 4-OH metabolites differentially influence RyR1 channel activity and ECC in embryonic skeletal muscle.	4-oh	28-32	ryanodine receptor 1, skeletal muscle	Mus musculus	70-74
21636218-1	2011	Patients with Gilbert syndrome have an impaired function of the enzyme UGT1A1, responsible for the degradation of 4-OH-estrogens.	4-oh	114-118	UDP glucuronosyltransferase family 1 member A1	Homo sapiens	71-77
19810737-1	2009	An assessment of the relative reactivities of the 4-OH of N-acetylglucosamine acceptors bearing simple protecting groups, beta-linked or alpha-linked D or L sugars at O-3 is presented, using a per-O-acetylated alpha-D-glucosyl trichloroacetimidate donor under activation by BF(3) x OEt(2).	4-oh	50-54	immunoglobulin kappa variable 2D-38 (pseudogene)	Homo sapiens	167-170
20513361-8	2010	HLM incubation data showed that 4-OH RA formation velocity varied from 0.2 to 15.3pmol/min/mg microsomal protein and velocity in HLMs was significantly correlated (p<0.01) to CYP26A1, CYP3A4, and CYP3A5 protein content, but not to CYP2C8.	4-oh	32-36	cytochrome P450 family 26 subfamily A member 1	Homo sapiens	178-185
20513361-8	2010	HLM incubation data showed that 4-OH RA formation velocity varied from 0.2 to 15.3pmol/min/mg microsomal protein and velocity in HLMs was significantly correlated (p<0.01) to CYP26A1, CYP3A4, and CYP3A5 protein content, but not to CYP2C8.	4-oh	32-36	cytochrome P450 family 3 subfamily A member 4	Homo sapiens	187-193
20513361-8	2010	HLM incubation data showed that 4-OH RA formation velocity varied from 0.2 to 15.3pmol/min/mg microsomal protein and velocity in HLMs was significantly correlated (p<0.01) to CYP26A1, CYP3A4, and CYP3A5 protein content, but not to CYP2C8.	4-oh	32-36	cytochrome P450 family 3 subfamily A member 5	Homo sapiens	199-205
20513361-8	2010	HLM incubation data showed that 4-OH RA formation velocity varied from 0.2 to 15.3pmol/min/mg microsomal protein and velocity in HLMs was significantly correlated (p<0.01) to CYP26A1, CYP3A4, and CYP3A5 protein content, but not to CYP2C8.	4-oh	32-36	cytochrome P450 family 2 subfamily C member 8	Homo sapiens	234-240
19810737-3	2009	On the other hand, the presence of peracetylated sugars at O-3 of N-acetylglucosamine acceptors did impact the reactivity of the 4-OH.	4-oh	129-133	immunoglobulin kappa variable 2D-38 (pseudogene)	Homo sapiens	59-62
18826295-1	2008	Extensive molecular docking, molecular dynamics simulations, and binding free energy calculations have been performed to understand how alpha7-specific agonists of nicotinic acetylcholine receptor (nAChR), including AR-R17779 (1), GTS-21 (4), and 4-OH-GTS-21 (5), interact with the alpha7 receptor, leading to important new insights into the receptor-agonist binding.	4-oh	247-251	cholinergic receptor nicotinic alpha 4 subunit	Homo sapiens	164-196
19588850-4	2009	Addition of antiserum against CYP2B4, a constitutive and PB-inducible rabbit P450 isoform, to a microsomal incubation system resulted in almost complete inhibition of the formation of 3-OH-, 4-OH- and 3,4-diOH-metabolites.	4-oh	191-195	cytochrome P450 2B4	Oryctolagus cuniculus	30-36
19635455-5	2009	Moreover, selection of tamoxifen-resistant MCF-7 cells, by long-term culture in presence of 4-OH tamoxifen, resulted in cells that display overexpression of PTP1B and TC-PTP, and concomitant increase in ERK and STAT3 phosphorylation.	4-oh	92-96	protein tyrosine phosphatase non-receptor type 1	Homo sapiens	157-162
19635455-5	2009	Moreover, selection of tamoxifen-resistant MCF-7 cells, by long-term culture in presence of 4-OH tamoxifen, resulted in cells that display overexpression of PTP1B and TC-PTP, and concomitant increase in ERK and STAT3 phosphorylation.	4-oh	92-96	protein tyrosine phosphatase non-receptor type 2	Homo sapiens	167-173
19635455-5	2009	Moreover, selection of tamoxifen-resistant MCF-7 cells, by long-term culture in presence of 4-OH tamoxifen, resulted in cells that display overexpression of PTP1B and TC-PTP, and concomitant increase in ERK and STAT3 phosphorylation.	4-oh	92-96	EPH receptor B2	Homo sapiens	203-206
19635455-5	2009	Moreover, selection of tamoxifen-resistant MCF-7 cells, by long-term culture in presence of 4-OH tamoxifen, resulted in cells that display overexpression of PTP1B and TC-PTP, and concomitant increase in ERK and STAT3 phosphorylation.	4-oh	92-96	signal transducer and activator of transcription 3	Homo sapiens	211-216
18826295-1	2008	Extensive molecular docking, molecular dynamics simulations, and binding free energy calculations have been performed to understand how alpha7-specific agonists of nicotinic acetylcholine receptor (nAChR), including AR-R17779 (1), GTS-21 (4), and 4-OH-GTS-21 (5), interact with the alpha7 receptor, leading to important new insights into the receptor-agonist binding.	4-oh	247-251	cholinergic receptor nicotinic alpha 4 subunit	Homo sapiens	198-203