maleic acid (CHEBI:18300)

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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

Average Mass

116.07216

Monoisotopic Mass

116.01096

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:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed
Arabidopsis thaliana (NCBI:txid3702)	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).

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-(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) 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
cis-ethene-1,2-dioic acid	ChEBI
H₂male	IUPAC
Maleic acid	KEGG COMPOUND
MALEIC ACID	PDBeChem
toxilic acid	NIST Chemistry WebBook

Last Modified

18 October 2023