PMID-sentid	Pub_year	Sent_text	compound_name	comp_offset	prot_official_name	organism	prot_offset
705026-3	1978	Of the potential pargyline metabolites tested, N-benzylpropargylamine and propargyl alcohol--like pargyline itself--readily inhibited AlDH in vivo but were without effect on the enzyme in vitro.	propargyl alcohol	74-91	aldehyde dehydrogenase 3 family, member A1	Rattus norvegicus	134-138
3707613-9	1986	Propargyl alcohol, a substance which is metabolized to propiolaldehyde by alcohol dehydrogenase, also inhibited AlDH in vivo and caused a quantitatively similar rise in blood acetaldehyde after ethanol as pargyline.	propargyl alcohol	0-17	aldehyde dehydrogenase 3 family, member A1	Rattus norvegicus	112-116
31851391-0	2020	Gold-catalyzed Iminations of Terminal Propargyl Alcohols with Anthranils with Atypical Chemoselectivity for C(1)-Additions and 1,2-Carbon Migration.	propargyl alcohol	38-56	heterogeneous nuclear ribonucleoprotein C	Homo sapiens	108-112
32374441-1	2020	Propargyl alcohols, on treatment with MHMDS (M = Na, K), B2(pin)2, an acid chloride and a palladium/copper co-catalyst system, undergo a reaction cascade comprised of trans-diboration, regioselective acylation, cyclization and dehydration to give trisubstituted furylboronic acid pinacol ester derivatives in good yields; subsequent Suzuki coupling allows a fourth substituent of choice to be introduced and hence tetrasubstituted (arylated) furans to be formed.	propargyl alcohol	0-18	telomeric repeat binding factor 1	Homo sapiens	57-65
31246037-2	2019	In contrast, indole-2-carboxylic acids/amides form fused seven-membered lactones/lactams (oxepinoindolones/azepinoindolones) upon treatment with substituted propargyl alcohols using catalytic Cu(OTf)2.	propargyl alcohol	157-175	POU class 2 homeobox 2	Homo sapiens	195-200
31912735-1	2020	A one-pot tandem reaction has been developed for the synthesis of substituted tetrahydropyrroloisoindolone via Mannich reaction of N-propargyl amido alcohols with 1,3-dicarbonyl compounds followed by Conia-ene cyclization reaction in moderate to good yields catalyzed by indium(III)triflate [In(OTf)3].	propargyl alcohol	131-157	POU class 5 homeobox 1	Homo sapiens	295-300
31912735-0	2020	In(OTf)3-Catalyzed One-Pot Tandem Mannich and Conia-Ene Cyclization Reaction of N-Propargyl Amido Alcohols with 1,3-Dicarbonyl Compounds: An Approach To Construct Tetrahydro-1H-pyrrolo[2,1-a]isoindolone-1,1-dicarboxylate and Its Application.	propargyl alcohol	80-106	POU class 5 homeobox 1	Homo sapiens	3-8
31025788-1	2019	Parahydrogen (p-H2 ) induced polarization (PHIP) NMR spectroscopy showed that [CpX Ru] complexes with greatly different electronic properties invariably engage propargyl alcohol derivatives into gem-hydrogenation with formation of pianostool ruthenium carbenes; in so doing, less electron rich CpX rings lower the barriers, stabilize the resulting complexes and hence provide opportunities for harnessing genuine carbene reactivity.	propargyl alcohol	160-177	polyhomeotic homolog 2	Homo sapiens	14-18
24398382-3	2014	The 3-alkynolyl-5-(4"-indazolyl)indazole-7-carboxamide derivatives were thus prepared, and in vitro evaluation of their inhibitory activity against the JAK isozymes revealed that the propargyl alcohol functionality endowed the 5-(4"-indazolyl)indazole-7-carboxamide scaffold with JAK1 selectivity over other JAK isozymes, particularly JAK2.	propargyl alcohol	183-200	Janus kinase 1	Homo sapiens	280-284
28718966-5	2017	Then, the regioselective anti-addition of HN3 to triple bond of active silver-acetylide or ethynyl carbinols affords product vinyl azide via Ag-C sigma-bond activation or Ag...C pi-coordination activation modes, and the former one is more favorable.	propargyl alcohol	91-108	MT-RNR2 like 3 (pseudogene)	Homo sapiens	42-45
27812589-1	2016	The carboxylative cyclization of a propargyl alcohol with CO2 mediated by a N-heterocyclic olefin (NHO) or N-heterocyclic carbene (NHC) has been comparatively studied using density functional theory (DFT) calculations.	propargyl alcohol	35-52	high mobility group nucleosomal binding domain 4	Homo sapiens	107-135
27812589-4	2016	(ii) As the basicity of the NHO is weaker than the NHC, deprotonation of the propargyl alcohol by the NHO is relatively more difficult.	propargyl alcohol	77-94	high mobility group nucleosomal binding domain 4	Homo sapiens	51-54
26351779-4	2015	DFT calculations were performed on the reacting complex of LGa with propargyl alcohol and show an OHGa hydrogen bond as the first interaction between the reagents.	propargyl alcohol	68-85	glutaminase 2	Homo sapiens	59-62
30993987-1	2019	Proper choice of the base allowed trans-diboration of propargyl alcohols with B2(pin)2 to evolve into an exquisitely regioselective procedure for net trans-carboboration.	propargyl alcohol	54-72	telomeric repeat binding factor 1	Homo sapiens	78-86
29898599-2	2018	Mechanistically, the formation of the title compounds is triggered by a Rh(III)-catalyzed C(sp2)-H alkenylation of N-nitrosoaniline with propargyl alcohol followed by the simultaneous intramolecular amination/cyclization, NO extrusion, and dehydration.	propargyl alcohol	137-154	Sp2 transcription factor	Homo sapiens	90-95
24398382-3	2014	The 3-alkynolyl-5-(4"-indazolyl)indazole-7-carboxamide derivatives were thus prepared, and in vitro evaluation of their inhibitory activity against the JAK isozymes revealed that the propargyl alcohol functionality endowed the 5-(4"-indazolyl)indazole-7-carboxamide scaffold with JAK1 selectivity over other JAK isozymes, particularly JAK2.	propargyl alcohol	183-200	Janus kinase 2	Homo sapiens	335-339
24423029-2	2014	1-Bromo-9-methyloctadecane (5) and hex-6-tetrahydropyranyloxyhex-2,4-diyn-1-al (9) which were initially synthesised separately starting from 1,8-octanediol (1) and propargyl alcohol (6), respectively, have been used as the final intermediates to obtain the title compound.	propargyl alcohol	164-181	hematopoietically expressed homeobox	Homo sapiens	35-38
23143924-1	2012	Pyrazoles direct: propargyl alcohols undergo hydrazination when treated with p-tosyl hydrazide in the presence of catalytic amounts of either Sc(OTf)(3) or La(OTf)(3) (see scheme; Tf=trifluoromethanesulfonyl).	propargyl alcohol	18-36	POU class 5 homeobox 1	Homo sapiens	156-165
19642681-9	2009	One of these mutants (ADAR2 R455A) was able to substantially overcome the inhibitory effect of the bulky C7 substituents (-Br, -I, propargyl alcohol).	propargyl alcohol	131-148	adenosine deaminase RNA specific B1	Homo sapiens	22-27
19831345-1	2009	[Ag(COD)(2)]PF(6) catalyzes the reaction between propargyl alcohols and N-tosylaziridines/azetidines leading to a diverse range of N,O-heterocycles, namely, oxazines, oxazepines, and oxazocines via ring-opening and ring-closing in a cascade.	propargyl alcohol	49-67	small nuclear ribonucleoprotein polypeptides B and B1	Homo sapiens	4-7
16277531-1	2005	Improved 1H ENDOR data from the S(EPR1) intermediate formed during turnover of the nitrogenase alpha-195Gln MoFe protein with C2(1,2)H2 in (1,2)H2O buffers, taken in context with the recent study of the intermediate formed from propargyl alcohol, indicate that S(EPR1) is a product complex, likely with C2H4 bound as a ferracycle to a single Fe of the FeMo-cofactor active site.	propargyl alcohol	228-245	baculoviral IAP repeat containing 5	Homo sapiens	34-38
16776526-1	2006	Zn(OTf)2 (10 mol %) catalyzed the cyclization of propargyl alcohols with PhXH (X = O, NH) in hot toluene (100 degrees C) without additive and gave indole and benzofuran products with different structures.	propargyl alcohol	49-67	POU class 2 homeobox 2	Homo sapiens	3-8
16331899-1	2005	The C 1s excitation spectra of propyne (HC2CH3), 3,3,3-trifluoropropyne (HC2CF3), and propargyl alcohol (HC3CH3OH) have been studied using synchrotron radiation and ion time-of-flight mass spectrometry.	propargyl alcohol	86-103	complement C1s	Homo sapiens	4-8
11306107-0	2001	Cytochrome P450 2E1 metabolically activates propargyl alcohol: propiolaldehyde-induced hepatocyte cytotoxicity.	propargyl alcohol	44-61	cytochrome P450, family 2, subfamily e, polypeptide 1	Rattus norvegicus	0-19
11306107-7	2001	Propargyl alcohol (2-propyn-1-ol), because of its structural similarity to allyl alcohol, was thought to be activated by alcohol dehydrogenase.	propargyl alcohol	0-17	aldo-keto reductase family 1 member A1	Rattus norvegicus	121-142
11306107-7	2001	Propargyl alcohol (2-propyn-1-ol), because of its structural similarity to allyl alcohol, was thought to be activated by alcohol dehydrogenase.	propargyl alcohol	19-32	aldo-keto reductase family 1 member A1	Rattus norvegicus	121-142
11306107-13	2001	GSH conjugate formation during propargyl alcohol metabolism by microsomal mixed function oxidase in the presence of GSH was also prevented by anti-rat CYP 2E1 or CYP 2E1 inhibitors, (3) cytotoxicity was prevented when lipid peroxidation was inhibited with antioxidants, desferoxamine (ferric chelator) or dithiothreitol.	propargyl alcohol	31-48	cytochrome P450, family 2, subfamily e, polypeptide 1	Rattus norvegicus	151-158
11306107-13	2001	GSH conjugate formation during propargyl alcohol metabolism by microsomal mixed function oxidase in the presence of GSH was also prevented by anti-rat CYP 2E1 or CYP 2E1 inhibitors, (3) cytotoxicity was prevented when lipid peroxidation was inhibited with antioxidants, desferoxamine (ferric chelator) or dithiothreitol.	propargyl alcohol	31-48	cytochrome P450, family 2, subfamily e, polypeptide 1	Rattus norvegicus	162-169
11306107-15	2001	All of this evidence suggests that propargyl alcohol-induced cytotoxicity involves metabolic activation by CYP 2E1 to form propiolaldehyde that causes hepatocyte lysis as a result of GSH depletion and lipid peroxidation.	propargyl alcohol	35-52	cytochrome P450, family 2, subfamily e, polypeptide 1	Rattus norvegicus	107-114
8075374-5	1994	In addition, 2-propyn-1-ol-derived 2-propyn-1-al inhibited the peroxidatic and catalytic activities of catalase, whereas 2-propen-1-ol-derived 2-propen-1-al had no effect on these activities of catalase.	propargyl alcohol	13-26	catalase	Bos taurus	103-111
24234062-1	1995	(Z,Z)-6,9-Dienes with straight C18-C23 chains were synthesized from linoleic acid, and a C17 chain was synthesized by hydrogenation of the corresponding 6,9-diyne prepared from propargyl alcohol.	propargyl alcohol	177-194	cytokine like 1	Homo sapiens	89-92
8075374-0	1994	Comparative oxidation of 2-propyn-1-ol with other low molecular weight unsaturated and saturated primary alcohols by bovine liver catalase in vitro.	propargyl alcohol	25-38	catalase	Bos taurus	130-138
8075374-2	1994	Accordingly, we have examined liver catalase as an alternative pathway for the oxidation or bioactivation of 2-propyn-1-ol to 2-propyn-1-al, a highly reactive alpha,beta-unsaturated aldehyde.	propargyl alcohol	109-122	catalase	Bos taurus	36-44
34406748-4	2021	We identified the system propargyl alcohol + pH2   allyl alcohol to yield 1H polarization in excess of P   13% by using only 50% enriched pH2 at a pressure of  1 bar.	propargyl alcohol	25-42	polyhomeotic homolog 2	Homo sapiens	45-48