itaconic acid (CHEBI:30838)

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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

Supplier Information	ChemicalBook:CB1454369, eMolecules:520938, ZINC000000001669

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Formulae

C5H6O4
C5H6O4

Net Charge

Average Mass

130.099

Monoisotopic Mass

130.02661

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

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

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	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.

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 a dicarboxylic fatty acid (CHEBI:189840) itaconic acid (CHEBI:30838) is a olefinic compound (CHEBI:78840) itaconic acid (CHEBI:30838) is conjugate acid of itaconate(2−) (CHEBI:17240)

Incoming	tensyuic acid (CHEBI:133873) has functional parent itaconic acid (CHEBI:30838) 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

Last Modified

24 February 2022