CHEBI:18300 - maleic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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
Supplier Information ChemicalBook:CB9666441, ChemicalBook:CB2112323, eMolecules:524832, ZINC000003802189
Download Molfile XML SDF
Wikipedia License
α-Linolenic acid, also known as alpha-linolenic acid (ALA) (from Greek alpha meaning "first" and linon meaning flax), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils. In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid. In physiological literature, it is listed by its lipid number, 18:3 (n−3). It is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is a regioisomer of gamma-linolenic acid (GLA), an 18:3 (n−6) fatty acid (i.e., a polyunsaturated omega-6 fatty acid with three double bonds).
Read full article at Wikipedia
Formula C4H4O4
Net Charge 0
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).
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-(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
Manual Xrefs Databases
C00007417 KNApSAcK
C01384 KEGG COMPOUND
DB04299 DrugBank
HMDB0000176 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 Reaxys Registry Number Reaxys
Citations
Last Modified
18 October 2023