CHEBI:18012 - fumaric acid

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ChEBI Name fumaric acid
ChEBI ID CHEBI:18012
Definition A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42743, CHEBI:5190, CHEBI:24124
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Formula C4H4O4
Net Charge 0
Average Mass 116.07220
Monoisotopic Mass 116.011
InChI InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
InChIKey VZCYOOQTPOCHFL-OWOJBTEDSA-N
SMILES OC(=O)\C=C\C(O)=O
Metabolite of Species Details
Chlamydomonas reinhardtii (NCBI:3055) 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): fundamental metabolite
Any metabolite produced by all living cells.
food acidity regulator
A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents.
Application(s): food acidity regulator
A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents.
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ChEBI Ontology
Outgoing fumaric acid (CHEBI:18012) has role food acidity regulator (CHEBI:64049)
fumaric acid (CHEBI:18012) has role fundamental metabolite (CHEBI:78675)
fumaric acid (CHEBI:18012) is a butenedioic acid (CHEBI:22958)
fumaric acid (CHEBI:18012) is conjugate acid of fumarate(1−) (CHEBI:37154)
Incoming (2E)-2-(methoxycarbonylmethyl)but-2-enedioic acid (CHEBI:15661) has functional parent fumaric acid (CHEBI:18012)
3-amino-N-(trans-3-carbamoyloxirane-2-carbonyl)-L-alanine (CHEBI:85509) has functional parent fumaric acid (CHEBI:18012)
N3-fumaramoyl-(S)-2,3-diaminopropanoic acid (CHEBI:85347) has functional parent fumaric acid (CHEBI:18012)
N3-fumaroyl-(S)-2,3-diaminopropanoic acid (CHEBI:85346) has functional parent fumaric acid (CHEBI:18012)
O-fumaryl-L-carnitine (CHEBI:85093) has functional parent fumaric acid (CHEBI:18012)
O-fumarylcarnitine (CHEBI:87264) has functional parent fumaric acid (CHEBI:18012)
dapdiamide (CHEBI:85331) has functional parent fumaric acid (CHEBI:18012)
diethyl fumarate (CHEBI:87388) has functional parent fumaric acid (CHEBI:18012)
dihydroxyfumaric acid (CHEBI:4593) has functional parent fumaric acid (CHEBI:18012)
dimethyl fumarate (CHEBI:76004) has functional parent fumaric acid (CHEBI:18012)
mesaconic acid (CHEBI:16600) has functional parent fumaric acid (CHEBI:18012)
fumarate(1−) (CHEBI:37154) is conjugate base of fumaric acid (CHEBI:18012)
(E)-3-carboxyprop-2-enoyl group (CHEBI:24126) is substituent group from fumaric acid (CHEBI:18012)
fumaroyl group (CHEBI:24125) is substituent group from fumaric acid (CHEBI:18012)
IUPAC Name
(2E)-but-2-enedioic acid
Synonyms Sources
(2E)-2-butenedioic acid NIST Chemistry WebBook
(E)-2-butenedioic acid NIST Chemistry WebBook
E297 ChEBI
Fumaric acid KEGG COMPOUND
FUMARIC ACID PDBeChem
Fumarsäure ChEBI
trans-1,2-ethylenedicarboxylic acid ChemIDplus
trans-but-2-enedioic acid IUPAC
trans-Butenedioic acid KEGG COMPOUND
Database Links Databases
3229 DrugCentral
C00001183 KNApSAcK
C00122 KEGG COMPOUND
D02308 KEGG DRUG
FUM PDBeChem
FUM MetaCyc
Fumaric_Acid Wikipedia
HMDB0000134 HMDB
View more database links
Registry Numbers Types Sources
110-17-8 CAS Registry Number KEGG COMPOUND
110-17-8 CAS Registry Number NIST Chemistry WebBook
110-17-8 CAS Registry Number ChemIDplus
49855 Gmelin Registry Number Gmelin
605763 Beilstein Registry Number Beilstein
605763 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17439666 PubMed citation Europe PMC
21414846 PubMed citation Europe PMC
22113915 PubMed citation Europe PMC
22217732 PubMed citation Europe PMC
22516248 PubMed citation Europe PMC
Last Modified
22 February 2017