CHEBI:18300 - maleic acid

ChEBI IDCHEBI:18300
ChEBI Namemaleic acid
Stars
DefinitionA butenedioic acid in which the double bond has cis- (Z)-configuration.
Secondary ChEBI IDsCHEBI:6653, CHEBI:25119, CHEBI:43836
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-UPHRSURJSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Arabidopsis thaliana (ncbitaxon:3702) leaf (BTO:0000713) PubMed (10952545)
Chlamydomonas reinhardtii (ncbitaxon:3055) - PubMed (25515814)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
algal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
ChEBI Ontology
Outgoing Relation(s)
maleic acid (CHEBI:18300) has role algal metabolite (CHEBI:84735)
maleic acid (CHEBI:18300) has role mouse metabolite (CHEBI:75771)
maleic acid (CHEBI:18300) has role plant metabolite (CHEBI:76924)
maleic acid (CHEBI:18300) is a butenedioic acid (CHEBI:22958)
maleic acid (CHEBI:18300) is conjugate acid of maleate (CHEBI:132951)
maleic acid (CHEBI:18300) is conjugate acid of maleate(1−) (CHEBI:37156)
Incoming Relation(s)
N-formylmaleamic acid (CHEBI:59930) has functional parent maleic acid (CHEBI:18300)
2-(ω-methylthio)alkylmaleic acid (CHEBI:134534) has functional parent maleic acid (CHEBI:18300)
2-isopropylmaleic acid (CHEBI:17275) has functional parent maleic acid (CHEBI:18300)
citraconic acid (CHEBI:17626) has functional parent maleic acid (CHEBI:18300)
dimethylmaleic acid (CHEBI:23812) has functional parent maleic acid (CHEBI:18300)
maleamic acid (CHEBI:29045) has functional parent maleic acid (CHEBI:18300)
maleate ester (CHEBI:35486) has functional parent maleic acid (CHEBI:18300)
maleimide (CHEBI:16072) has functional parent maleic acid (CHEBI:18300)
maleimides (CHEBI:55417) has functional parent maleic acid (CHEBI:18300)
maleate (CHEBI:132951) is conjugate base of maleic acid (CHEBI:18300)
maleate(1−) (CHEBI:37156) is conjugate base of maleic acid (CHEBI:18300)
(Z)-3-carboxyprop-2-enoyl group (CHEBI:25122) is substituent group from maleic acid (CHEBI:18300)
maleoyl group (CHEBI:25121) is substituent group from maleic acid (CHEBI:18300)
IUPAC Name 
(2Z)-but-2-enedioic acid
Synonyms  Source
Maleic acidKEGG COMPOUND
cis-Butenedioic acidKEGG COMPOUND
cis-but-2-enedioic acidIUPAC
H2maleIUPAC
(Z)-2-butenedioic acidNIST Chemistry WebBook
(Z)-butenedioic acidNIST Chemistry WebBook
Manual XrefsDatabases
C01384KEGG COMPOUND
C01384KEGG COMPOUND
MAEPDBeChem
DB04299DrugBank
HMDB0000176HMDB
MALEATEMetaCyc
Maleic_acidWikipedia
C00007417KNApSAcK
Registry NumbersSources
Gmelin:49854Gmelin
Beilstein:1903639Beilstein
Reaxys:605762Reaxys
CAS:110-16-7KEGG COMPOUND
CAS:110-16-7ChemIDplus
CAS:110-16-7NIST Chemistry WebBook
Citations