CHEBI:6650 - malic acid

Main ChEBI Ontology Automatic Xrefs
ChEBI Name malic acid
ChEBI ID CHEBI:6650
Definition A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Save molfile Download Molfile
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C4H6O5
Net Charge 0
Average Mass 134.08744
InChI InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
InChIKey BJEPYKJPYRNKOW-UHFFFAOYSA-N
SMILES OC(CC(O)=O)C(O)=O
Metabolite of Species Details
Daphnia magna (NCBI:35525) See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyond
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): fundamental metabolite
Any metabolite produced by all living cells.
food acidity regulator
A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents.
Application(s): food acidity regulator
A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing malic acid (CHEBI:6650) has functional parent succinic acid (CHEBI:15741)
malic acid (CHEBI:6650) has role food acidity regulator (CHEBI:64049)
malic acid (CHEBI:6650) has role fundamental metabolite (CHEBI:78675)
malic acid (CHEBI:6650) is a 2-hydroxydicarboxylic acid (CHEBI:50263)
malic acid (CHEBI:6650) is a C4-dicarboxylic acid (CHEBI:66873)
malic acid (CHEBI:6650) is conjugate acid of malate(2−) (CHEBI:15595)
Incoming 2,3-dimethylmalic acid (CHEBI:15590) has functional parent malic acid (CHEBI:6650)
malate ester (CHEBI:36188) has functional parent malic acid (CHEBI:6650)
(R)-malic acid (CHEBI:30796) is a malic acid (CHEBI:6650)
(S)-malic acid (CHEBI:30797) is a malic acid (CHEBI:6650)
malate(2−) (CHEBI:15595) is conjugate base of malic acid (CHEBI:6650)
IUPAC Name
2-hydroxybutanedioic acid
Synonyms Sources
2-Hydroxybutanedioic acid KEGG COMPOUND
2-Hydroxyethane-1,2-dicarboxylic acid HMDB
2-Hydroxysuccinic acid HMDB
α-hydroxysuccinic acid HMDB
Äpfelsäure ChEBI
apple acid NIST Chemistry WebBook
DL-Malic acid HMDB
E296 ChEBI
H2mal IUPAC
hydroxybutanedioic acid NIST Chemistry WebBook
hydroxysuccinic acid NIST Chemistry WebBook
Malic acid KEGG COMPOUND
Database Links Databases
C00711 KEGG COMPOUND
D04843 KEGG DRUG
HMDB00744 HMDB
Malic_acid Wikipedia
RS-Malate MetaCyc
View more database links
Registry Numbers Types Sources
1723539 Reaxys Registry Number Reaxys
1723539 Beilstein Registry Number Beilstein
3325 Gmelin Registry Number Gmelin
6915-15-7 CAS Registry Number NIST Chemistry WebBook
6915-15-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15767321 PubMed citation CiteXplore
17190852 PubMed citation CiteXplore
17439666 PubMed citation CiteXplore
17896933 PubMed citation CiteXplore
19743855 PubMed citation CiteXplore
22411507 PubMed citation CiteXplore
Last Modified
02 March 2015