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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
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 Oct
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 Jun
Fluorinated analogues as mechanistic probes in valproic acid hepatotoxicity: hepatic microvesicular steatosis and glutathione status.
1995 Jul-Aug
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 Sep 28
Histone deacetylases inhibition and tumor cells cytotoxicity by CNS-active VPA constitutional isomers and derivatives.
2005 May 15
Science review: carnitine in the treatment of valproic acid-induced toxicity - what is the evidence?
2005 Oct 5
Contribution of CYP2C9, CYP2A6, and CYP2B6 to valproic acid metabolism in hepatic microsomes from individuals with the CYP2C9*1/*1 genotype.
2006 Dec
Quantification of valproic acid and its metabolite 2-propyl-4-pentenoic acid in human plasma using HPLC-MS/MS.
2007 May 1
Pyruvate uptake is inhibited by valproic acid and metabolites in mitochondrial membranes.
2008 Oct 15
The relationship between glucuronide conjugate levels and hepatotoxicity after oral administration of valproic acid.
2009 Jul
Formulations of valproate alter valproate metabolism: a single oral dose kinetic study.
2009 Oct
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 Dec
Dose-dependent pharmacokinetics of toxic metabolites is not related to increased toxicity following high-dose valproic acid in rats.
2010 Nov
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Dec 16 08:03:39 GMT 2023
Edited
by admin
on Sat Dec 16 08:03:39 GMT 2023
Record UNII
2GYI36I25W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
.DELTA.4-VALPROIC ACID
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID20881257
Created by admin on Sat Dec 16 08:03:39 GMT 2023 , Edited by admin on Sat Dec 16 08:03:39 GMT 2023
PRIMARY
CAS
1575-72-0
Created by admin on Sat Dec 16 08:03:39 GMT 2023 , Edited by admin on Sat Dec 16 08:03:39 GMT 2023
PRIMARY
FDA UNII
2GYI36I25W
Created by admin on Sat Dec 16 08:03:39 GMT 2023 , Edited by admin on Sat Dec 16 08:03:39 GMT 2023
PRIMARY
PUBCHEM
104896
Created by admin on Sat Dec 16 08:03:39 GMT 2023 , Edited by admin on Sat Dec 16 08:03:39 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE TOXIC
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