CHEBI:39867 - valproic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name valproic acid
ChEBI ID CHEBI:39867
Definition A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:9926, CHEBI:39858, CHEBI:115217
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C8H16O2
Net Charge 0
Average Mass 144.21140
Monoisotopic Mass 144.115
InChI InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)
InChIKey NIJJYAXOARWZEE-UHFFFAOYSA-N
SMILES CCCC(CCC)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): GABA agent
A substance, such as agonists, antagonists, degradation or uptake inhibitors, depleters, precursors, and modulators of receptor function, used for its pharmacological actions on GABAergic systems.
EC 3.5.1.98 (histone deacetylase) inhibitor
An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98).
teratogenic agent
A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
Application(s): GABA agent
A substance, such as agonists, antagonists, degradation or uptake inhibitors, depleters, precursors, and modulators of receptor function, used for its pharmacological actions on GABAergic systems.
anticonvulsant
A drug used to prevent seizures or reduce their severity.
psychotropic drug
A loosely defined grouping of drugs that have effects on psychological function.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
antimanic drug
Antimanic drugs are agents used to treat bipolar disorders or mania associated with other affective disorders.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing valproic acid (CHEBI:39867) has functional parent valeric acid (CHEBI:17418)
valproic acid (CHEBI:39867) has role anticonvulsant (CHEBI:35623)
valproic acid (CHEBI:39867) has role antimanic drug (CHEBI:35477)
valproic acid (CHEBI:39867) has role EC 3.5.1.98 (histone deacetylase) inhibitor (CHEBI:61115)
valproic acid (CHEBI:39867) has role GABA agent (CHEBI:51374)
valproic acid (CHEBI:39867) has role neuroprotective agent (CHEBI:63726)
valproic acid (CHEBI:39867) has role psychotropic drug (CHEBI:35471)
valproic acid (CHEBI:39867) has role teratogenic agent (CHEBI:50905)
valproic acid (CHEBI:39867) is a branched-chain fatty acid (CHEBI:35819)
valproic acid (CHEBI:39867) is a branched-chain saturated fatty acid (CHEBI:39417)
valproic acid (CHEBI:39867) is conjugate acid of valproate (CHEBI:60654)
Incoming valpromide (CHEBI:74562) has functional parent valproic acid (CHEBI:39867)
valproate semisodium (CHEBI:4667) has part valproic acid (CHEBI:39867)
valproate (CHEBI:60654) is conjugate base of valproic acid (CHEBI:39867)
IUPAC Name
2-propylpentanoic acid
INNs Sources
acide valproïque ChemIDplus
ácido valproico ChemIDplus
acidum valproicum ChemIDplus
valproic acid ChemIDplus
Synonyms Sources
2-n-propyl-n-valeric acid NIST Chemistry WebBook
2-PROPYL-PENTANOIC ACID PDBeChem
2-propylpentanoic acid ChEMBL
2-propylvaleric acid ChemIDplus
4-heptanecarboxylic acid ChemIDplus
di-n-propylacetic acid ChemIDplus
Di-n-propylessigsäure ChemIDplus
dipropylacetic acid NIST Chemistry WebBook
DPA NIST Chemistry WebBook
n-DPA DrugBank
VALPROIC ACID ChEMBL
Valproinsäure ChEBI
VPA ChEBI
Brand Name Source
Depakene KEGG DRUG
Manual Xrefs Databases
2803 DrugCentral
2PP PDBeChem
C07185 KEGG COMPOUND
D00399 KEGG DRUG
DB00313 DrugBank
HMDB0001877 HMDB
LMFA01020291 LIPID MAPS
LSM-4620 LINCS
Valproic_Acid Wikipedia
View more database links
Registry Numbers Types Sources
1750447 Beilstein Registry Number ChemIDplus
1750447 Reaxys Registry Number Reaxys
99-66-1 CAS Registry Number ChemIDplus
99-66-1 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
11716839 PubMed citation Europe PMC
12475192 PubMed citation Europe PMC
15124690 PubMed citation Europe PMC
15560954 PubMed citation Europe PMC
15578701 PubMed citation Europe PMC
16496131 PubMed citation Europe PMC
16621443 PubMed citation Europe PMC
16759735 PubMed citation Europe PMC
17156483 PubMed citation Europe PMC
17273758 PubMed citation Europe PMC
19280426 PubMed citation Europe PMC
19318486 PubMed citation Europe PMC
23792104 PubMed citation Europe PMC
23810771 PubMed citation Europe PMC
23949302 PubMed citation Europe PMC
24135375 PubMed citation Europe PMC
24200999 PubMed citation Europe PMC
24348849 PubMed citation Europe PMC
8558327 PubMed citation Europe PMC
8681902 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2011-02-11 An anti-epilectic and anti-carcinogenic drug with toxic and teratogenic properties, which dissolves to valproate in the gut.