CHEBI:16600 - mesaconic acid

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ChEBI Name mesaconic acid
ChEBI ID CHEBI:16600
Definition A dicarboxylic acid consisting of fumaric acid having a methyl substituent at the 2-position.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43999, CHEBI:6772, CHEBI:19701
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Formula C5H6O4
Net Charge 0
Average Mass 130.09874
Monoisotopic Mass 130.027
InChI InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+
InChIKey HNEGQIOMVPPMNR-NSCUHMNNSA-N
SMILES C\C(=C/C(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).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing mesaconic acid (CHEBI:16600) has functional parent fumaric acid (CHEBI:18012)
mesaconic acid (CHEBI:16600) has role human metabolite (CHEBI:77746)
mesaconic acid (CHEBI:16600) has role plant metabolite (CHEBI:76924)
mesaconic acid (CHEBI:16600) is a dicarboxylic acid (CHEBI:35692)
mesaconic acid (CHEBI:16600) is conjugate acid of mesaconate(2−) (CHEBI:36986)
Incoming 3-methylfumaryl-CoA (CHEBI:75856) has functional parent mesaconic acid (CHEBI:16600)
mesaconyl-CoA (CHEBI:27969) has functional parent mesaconic acid (CHEBI:16600)
mesaconate(2−) (CHEBI:36986) is conjugate base of mesaconic acid (CHEBI:16600)
IUPAC Name
(2E)-2-methylbut-2-enedioic acid
Synonyms Sources
(E)-2-Methyl-2-butenedioic acid KEGG COMPOUND
(E)-Citraconic acid HMDB
2-methylfumaric acid ChEBI
Citronic acid HMDB
Mesaconic acid KEGG COMPOUND
Methylfumaric acid KEGG COMPOUND
trans-1-Propene-1,2-dicarboxylic acid ChemIDplus
trans-2-Methyl-2-butenedioic acid NIST Chemistry WebBook
Manual Xrefs Databases
C01732 KEGG COMPOUND
HMDB0000749 HMDB
Mesaconic_acid Wikipedia
MEZ PDBeChem
View more database links
Registry Numbers Types Sources
1722680 Reaxys Registry Number Reaxys
498-24-8 CAS Registry Number KEGG COMPOUND
498-24-8 CAS Registry Number NIST Chemistry WebBook
498-24-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16744171 PubMed citation Europe PMC
6452974 PubMed citation Europe PMC
6778884 PubMed citation Europe PMC
Last Modified
16 July 2015