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Details

Stereochemistry RACEMIC
Molecular Formula C8H14O2
Molecular Weight 142.1956
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-PROPYL-4-PENTENOIC ACID

SMILES

CCCC(CC=C)C(O)=O

InChI

InChIKey=UMYDNZXEHYSVFY-UHFFFAOYSA-N
InChI=1S/C8H14O2/c1-3-5-7(6-4-2)8(9)10/h3,7H,1,4-6H2,2H3,(H,9,10)

HIDE SMILES / InChI

Molecular Formula C8H14O2
Molecular Weight 142.1956
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Approval Year

PubMed

PubMed

TitleDatePubMed
Role of oxidative metabolism in the effect of valproic acid on markers of cell viability, necrosis, and oxidative stress in sandwich-cultured rat hepatocytes.
2010-12
Dose-dependent pharmacokinetics of toxic metabolites is not related to increased toxicity following high-dose valproic acid in rats.
2010-11
Formulations of valproate alter valproate metabolism: a single oral dose kinetic study.
2009-10
The relationship between glucuronide conjugate levels and hepatotoxicity after oral administration of valproic acid.
2009-07
Pyruvate uptake is inhibited by valproic acid and metabolites in mitochondrial membranes.
2008-10-15
Quantification of valproic acid and its metabolite 2-propyl-4-pentenoic acid in human plasma using HPLC-MS/MS.
2007-05-01
Contribution of CYP2C9, CYP2A6, and CYP2B6 to valproic acid metabolism in hepatic microsomes from individuals with the CYP2C9*1/*1 genotype.
2006-12
Science review: carnitine in the treatment of valproic acid-induced toxicity - what is the evidence?
2005-10-05
Histone deacetylases inhibition and tumor cells cytotoxicity by CNS-active VPA constitutional isomers and derivatives.
2005-05-15
Differential effect of valproate and its Delta2- and Delta4-unsaturated metabolites, on the beta-oxidation rate of long-chain and medium-chain fatty acids.
2001-09-28
Fluorinated analogues as mechanistic probes in valproic acid hepatotoxicity: hepatic microvesicular steatosis and glutathione status.
1995-07-01
On the development of alternative antiepileptic drugs. Lack of enantioselectivity of the anticonvulsant activity, in contrast to teratogenicity, of 2-n-propyl-4-pentenoic acid and 2-n-propyl-4-pentynoic acid, analogues of the anticonvulsant drug valproic acid.
1991-06
Asymmetric synthesis and enantioselective teratogenicity of 2-n-propyl-4-pentenoic acid (4-en-VPA), an active metabolite of the anticonvulsant drug, valproic acid.
1989-10
Patents

Patents

Substance Class Chemical
Created
by admin
on Mon Mar 31 21:51:21 GMT 2025
Edited
by admin
on Mon Mar 31 21:51:21 GMT 2025
Record UNII
2GYI36I25W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.DELTA.4-VALPROIC ACID
Preferred Name English
2-PROPYL-4-PENTENOIC ACID
Systematic Name English
PENTANOIC ACID, 2-(2-PROPENYL)-
Common Name English
VALPROIC ACID METABOLITE .DELTA.4-VALPROIC ACID
Common Name English
(±)-2-N-PROPYL-4-PENTENOIC ACID
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID20881257
Created by admin on Mon Mar 31 21:51:21 GMT 2025 , Edited by admin on Mon Mar 31 21:51:21 GMT 2025
PRIMARY
CAS
1575-72-0
Created by admin on Mon Mar 31 21:51:21 GMT 2025 , Edited by admin on Mon Mar 31 21:51:21 GMT 2025
PRIMARY
FDA UNII
2GYI36I25W
Created by admin on Mon Mar 31 21:51:21 GMT 2025 , Edited by admin on Mon Mar 31 21:51:21 GMT 2025
PRIMARY
PUBCHEM
104896
Created by admin on Mon Mar 31 21:51:21 GMT 2025 , Edited by admin on Mon Mar 31 21:51:21 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> METABOLITE TOXIC
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URINE