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CHEBI:18300 - maleic acid

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ChEBI Name maleic acid
ChEBI ID CHEBI:18300
Definition A butenedioic acid in which the double bond has cis- (Z)-configuration.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43836, CHEBI:6653, CHEBI:25119
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Formula C4H4O4
Net Charge 0
Average Mass 116.07216
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-UPHRSURJSA-N
SMILES OC(=O)\C=C/C(O)=O
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:3055) See: PubMed
Arabidopsis thaliana (NCBI:3702) Found in leaf (BTO:0000713). 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): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 2-isopropylmaleic acid (CHEBI:17275) has functional parent maleic acid (CHEBI:18300)
N-formylmaleamic acid (CHEBI:59930) 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 Sources
(Z)-2-butenedioic acid NIST Chemistry WebBook
(Z)-butenedioic acid NIST Chemistry WebBook
cis-1,2-ethylenedicarboxylic acid NIST Chemistry WebBook
cis-but-2-enedioic acid IUPAC
cis-Butenedioic acid KEGG COMPOUND
H2male IUPAC
Maleic acid KEGG COMPOUND
MALEIC ACID PDBeChem
toxilic acid NIST Chemistry WebBook
Database Links Databases
C00007417 KNApSAcK
C01384 KEGG COMPOUND
DB04299 DrugBank
HMDB00176 HMDB
MAE PDBeChem
MALEATE MetaCyc
Maleic_acid Wikipedia
View more database links
Registry Numbers Types Sources
110-16-7 CAS Registry Number KEGG COMPOUND
110-16-7 CAS Registry Number ChemIDplus
110-16-7 CAS Registry Number NIST Chemistry WebBook
1903639 Beilstein Registry Number Beilstein
49854 Gmelin Registry Number Gmelin
605762 Beilstein Registry Number Beilstein
605762 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10952545 PubMed citation Europe PMC
11386868 PubMed citation Europe PMC
22770225 PubMed citation Europe PMC
9591280 PubMed citation Europe PMC
Last Modified
09 August 2016