CHEBI:30838 - itaconic acid

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ChEBI Name itaconic acid
ChEBI ID CHEBI:30838
Definition A dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6074, CHEBI:24933
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Formula C5H6O4
Net Charge 0
Average Mass 130.09874
InChI InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
InChIKey LVHBHZANLOWSRM-UHFFFAOYSA-N
SMILES OC(=O)CC(=C)C(O)=O
Metabolite of Species Details
Homo sapiens (NCBI:9606) See: PubMed
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): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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ChEBI Ontology
Outgoing itaconic acid (CHEBI:30838) has functional parent succinic acid (CHEBI:15741)
itaconic acid (CHEBI:30838) has role fungal metabolite (CHEBI:76946)
itaconic acid (CHEBI:30838) has role human metabolite (CHEBI:77746)
itaconic acid (CHEBI:30838) is a dicarboxylic acid (CHEBI:35692)
itaconic acid (CHEBI:30838) is conjugate acid of itaconate(2−) (CHEBI:17240)
Incoming itaconate(2−) (CHEBI:17240) is conjugate base of itaconic acid (CHEBI:30838)
IUPAC Name
2-methylidenebutanedioic acid
Synonyms Sources
2-methylenesuccinic acid NIST Chemistry WebBook
2-propene-1,2-dicarboxylic acid NIST Chemistry WebBook
Itaconic acid KEGG COMPOUND
methylenebutanedioic acid NIST Chemistry WebBook
Methylenesuccinic acid KEGG COMPOUND
propylenedicarboxylic acid NIST Chemistry WebBook
Database Links Databases
C00033964 KNApSAcK
C00490 KEGG COMPOUND
ECMDB02092 ECMDB
HMDB02092 HMDB
ITACONATE MetaCyc
Itaconic_acid Wikipedia
LMFA01170063 LIPID MAPS
YMDB00716 YMDB
View more database links
Registry Numbers Types Sources
1759501 Beilstein Registry Number Beilstein
1759501 Reaxys Registry Number Reaxys
240640 Gmelin Registry Number Gmelin
97-65-4 CAS Registry Number KEGG COMPOUND
97-65-4 CAS Registry Number ChemIDplus
97-65-4 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
18584171 PubMed citation CiteXplore
23420787 PubMed citation CiteXplore
23610393 PubMed citation CiteXplore
24169454 PubMed citation CiteXplore
Last Modified
16 July 2015