PMID-sentid	Pub_year	Sent_text	compound_name	comp_offset	prot_official_name	organism	prot_offset
9353388-0	1997	Human CYP2C9 and CYP2A6 mediate formation of the hepatotoxin 4-ene-valproic acid.	2-propyl-4-pentenoic acid	61-80	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	6-12
16945988-2	2006	cDNA-expressed CYP2C9*1, CYP2A6, and CYP2B6 were the most active catalysts of 4-ene-VPA, 4-OH-VPA, and 5-OH-VPA formation.	2-propyl-4-pentenoic acid	78-87	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	15-21
16945988-2	2006	cDNA-expressed CYP2C9*1, CYP2A6, and CYP2B6 were the most active catalysts of 4-ene-VPA, 4-OH-VPA, and 5-OH-VPA formation.	2-propyl-4-pentenoic acid	78-87	cytochrome P450 family 2 subfamily A member 6	Homo sapiens	25-31
16945988-2	2006	cDNA-expressed CYP2C9*1, CYP2A6, and CYP2B6 were the most active catalysts of 4-ene-VPA, 4-OH-VPA, and 5-OH-VPA formation.	2-propyl-4-pentenoic acid	78-87	cytochrome P450 family 2 subfamily B member 6	Homo sapiens	37-43
16945988-9	2006	Overall, our novel findings indicate that in human hepatic microsomes, CYP2C9*1 is the predominant catalyst in the formation of 4-ene-VPA, 4-OH-VPA, and 5-OH-VPA, whereas CYP2A6 contributes partially to 3-OH-VPA formation.	2-propyl-4-pentenoic acid	128-137	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	71-77
14597963-4	2003	The formation rates of 4-ene-VPA, 4-OH-VPA, and 5-OH-VPA in human liver microsomes were reduced by 29, 28, and 31%, respectively, in samples with one mutated CYP2C9 allele, and by 61, 73, and 58%, respectively, in samples with two mutated CYP2C9 alleles.	2-propyl-4-pentenoic acid	23-32	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	158-164
14597963-4	2003	The formation rates of 4-ene-VPA, 4-OH-VPA, and 5-OH-VPA in human liver microsomes were reduced by 29, 28, and 31%, respectively, in samples with one mutated CYP2C9 allele, and by 61, 73, and 58%, respectively, in samples with two mutated CYP2C9 alleles.	2-propyl-4-pentenoic acid	23-32	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	239-245
9353388-0	1997	Human CYP2C9 and CYP2A6 mediate formation of the hepatotoxin 4-ene-valproic acid.	2-propyl-4-pentenoic acid	61-80	cytochrome P450 family 2 subfamily A member 6	Homo sapiens	17-23
1678414-6	1991	Higher concentrations of 4enVPA significantly decreased the trypan blue exclusion as well as increased GOT and GPT leakage of hepatocytes.	2-propyl-4-pentenoic acid	25-31	alanine aminotransferase 1	Cavia porcellus	111-114
28273397-7	2017	Only CYP2A6 polymorphisms had associations with the concentrations of 4-ene-VPA and 2,4-diene-VPA.	2-propyl-4-pentenoic acid	70-79	cytochrome P450 family 2 subfamily A member 6	Homo sapiens	5-11
3138238-2	1988	The cytochrome P-450-mediated desaturation of valproic acid (VPA) to its hepatotoxic metabolite, 2-n-propyl-4-pentenoic acid (4-ene-VPA), was examined in liver microsomes from rats, mice, rabbits and humans.	2-propyl-4-pentenoic acid	97-124	cytochrome P450, family 2, subfamily g, polypeptide 1	Rattus norvegicus	4-20
3138238-2	1988	The cytochrome P-450-mediated desaturation of valproic acid (VPA) to its hepatotoxic metabolite, 2-n-propyl-4-pentenoic acid (4-ene-VPA), was examined in liver microsomes from rats, mice, rabbits and humans.	2-propyl-4-pentenoic acid	126-135	cytochrome P450, family 2, subfamily g, polypeptide 1	Rattus norvegicus	4-20
2870898-1	1986	2-n-Propyl-4-pentenoic acid (delta 4-VPA), an unsaturated metabolite of valproic acid (VPA), and the ethyl ester of delta 4-VPA were tested for their ability to cause NADPH- and time-dependent loss of cytochrome P-450 in hepatic microsomal preparations from phenobarbital-pretreated rats.	2-propyl-4-pentenoic acid	0-27	cytochrome P450, family 2, subfamily g, polypeptide 1	Rattus norvegicus	201-217
2870898-5	1986	In microsomes, both delta 4-VPA and its ethyl ester were metabolized by cytochrome P-450 to a common cyclic end-product, 3-n-propyl-5-hydroxymethyltetrahydro-2-furanone, although stable isotope labeling experiments with oxygen-18 demonstrated that the pathways followed by the two substrates were mechanistically distinct.	2-propyl-4-pentenoic acid	20-31	cytochrome P450, family 2, subfamily g, polypeptide 1	Rattus norvegicus	72-88
28273397-11	2017	However, only the CYP2A6 polymorphism was found to be associated with concentrations of 4-ene-VPA and 2,4-diene-VPA.	2-propyl-4-pentenoic acid	88-97	cytochrome P450 family 2 subfamily A member 6	Homo sapiens	18-24
20602621-3	2010	The formation of 4-ene-VPA is catalyzed by cytochrome P450 2C9 (CYP2C9).	2-propyl-4-pentenoic acid	17-26	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	43-62
20602621-3	2010	The formation of 4-ene-VPA is catalyzed by cytochrome P450 2C9 (CYP2C9).	2-propyl-4-pentenoic acid	17-26	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	64-70
20602621-5	2010	In the present work, VPA, 2-ene-VPA, and 4-ene-VPA in serum of patients receiving VPA were determined and the correlation between CYP2C9 polymorphism and 4-ene-VPA concentration was examined.	2-propyl-4-pentenoic acid	154-163	cytochrome P450 family 2 subfamily C member 9	Homo sapiens	130-136