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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:
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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.
ChEBI Ontology
Outgoing Relation(s)
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
(2E)-2-butenedioic acidNIST Chemistry WebBook
E297ChEBI
Fumaric acidKEGG COMPOUND
FUMARIC ACIDPDBeChem
FumarsäureChEBI
(E)-2-butenedioic acidNIST Chemistry WebBook
Manual XrefsDatabases
1347PPDB
3229DrugCentral
C00001183KNApSAcK
C00122KEGG COMPOUND
D02308KEGG DRUG
DB01677DrugBank
FDB003291FooDB
FUMPDBeChem
FUMMetaCyc
Fumaric_AcidWikipedia
HMDB0000134HMDB
Registry NumbersSources
Gmelin:49855Gmelin
Reaxys:605763Reaxys
CAS:110-17-8NIST Chemistry WebBook
CAS:110-17-8ChemIDplus
CAS:110-17-8KEGG COMPOUND
Citations