EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:18012 - fumaric acid

Default Structure
ChEBI IDCHEBI:18012
ChEBI Namefumaric acid
Stars
DefinitionA butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.
Secondary ChEBI IDsCHEBI:5190, CHEBI:24124, CHEBI:42743
Last Modified18 October 2023
DownloadsMolfile
FormulaC4H4O4
Net Charge0
Average Mass116.072
Monoisotopic Mass116.01096
SMILESO=C(O)/C=C/C(=O)O
InChIInChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
InChIKeyVZCYOOQTPOCHFL-OWOJBTEDSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Chlamydomonas reinhardtii (ncbitaxon:3055) - PubMed (25515814)
Roles Classification
Chemical Roles:
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.
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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.
Applications:
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.
antipsoriatic  A drug used to treat psoriasis.
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
ChEBI Ontology
Outgoing Relation(s)
fumaric acid (CHEBI:18012) has role antipsoriatic (CHEBI:50748)
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) has role geroprotector (CHEBI:176497)
fumaric acid (CHEBI:18012) is a butenedioic acid (CHEBI:22958)
fumaric acid (CHEBI:18012) is conjugate acid of fumarate(1−) (CHEBI:37154)
Incoming Relation(s)
(2E)-2-(methoxycarbonylmethyl)but-2-enedioic acid (CHEBI:15661) 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)
3-amino-N-(trans-3-carbamoyloxirane-2-carbonyl)-L-alanine (CHEBI:85509) 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)
monomethyl fumarate (CHEBI:167450) 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  Source
2-butenedioic acid, (e)-ChEMBL
(2E)-2-butenedioic acidNIST Chemistry WebBook
Allomaleic-acidChEMBL
Boletic-acidChEMBL
E-297ChEMBL
E297ChEBI
Manual XrefsDatabases
1347PPDB
3229DrugCentral
C00001183KNApSAcK
C00122KEGG COMPOUND
D02308KEGG DRUG
DB01677DrugBank
FDB003291FooDB
FUMMetaCyc
FUMPDBeChem
Fumaric_AcidWikipedia
HMDB0000134HMDB
Registry NumbersSources
Gmelin:49855Gmelin
Reaxys:605763Reaxys
CAS:110-17-8ChemIDplus
CAS:110-17-8NIST Chemistry WebBook
CAS:110-17-8KEGG COMPOUND
Citations