CHEBI:15584 - citramalic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name citramalic acid
ChEBI ID CHEBI:15584
Definition A 2-hydroxydicarboxylic acid that is malic acid (hydroxysuccinic acid) in which the hydrogen at position 2 is substituted by a methyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:23319, CHEBI:3725
Supplier Information
Download Molfile XML SDF
Formula C5H8O5
Net Charge 0
Average Mass 148.11400
Monoisotopic Mass 148.03717
InChI InChI=1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)
InChIKey XFTRTWQBIOMVPK-UHFFFAOYSA-N
SMILES CC(O)(CC(O)=O)C(O)=O
Metabolite of Species Details
Chlamydomonas reinhardtii (NCBI:txidtxid3055) See: PubMed
Malus domestica (NCBI:txidtxid3750) See: PubMed
Homo sapiens (NCBI:txidtxid9606) 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): 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.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing citramalic acid (CHEBI:15584) has functional parent succinic acid (CHEBI:15741)
citramalic acid (CHEBI:15584) has role algal metabolite (CHEBI:84735)
citramalic acid (CHEBI:15584) has role human metabolite (CHEBI:77746)
citramalic acid (CHEBI:15584) has role plant metabolite (CHEBI:76924)
citramalic acid (CHEBI:15584) is a 2-hydroxydicarboxylic acid (CHEBI:50263)
citramalic acid (CHEBI:15584) is a 3-hydroxy carboxylic acid (CHEBI:61355)
citramalic acid (CHEBI:15584) is conjugate acid of citramalate(2−) (CHEBI:13997)
Incoming D-citramalic acid (CHEBI:15586) is a citramalic acid (CHEBI:15584)
L-citramalic acid (CHEBI:29003) is a citramalic acid (CHEBI:15584)
citramalate(2−) (CHEBI:13997) is conjugate base of citramalic acid (CHEBI:15584)
IUPAC Name
2-hydroxy-2-methylbutanedioic acid
Synonyms Sources
(±)-2-hydroxy-2-methylsuccinic acid ChEBI
2-hydroxy-2-methylbutanedioic acid ChEBI
2-hydroxy-2-methylsuccinic acid ChEBI
2-Methylmalic acid KEGG COMPOUND
2-methylmalic acid ChEBI
alpha-Hydroxypyrotartaric acid KEGG COMPOUND
alpha-hydroxypyrotartaric acid ChEBI
Citramalic acid KEGG COMPOUND
citramalic acids ChEBI
Manual Xrefs Databases
C00001181 KNApSAcK
C00815 KEGG COMPOUND
HMDB0000426 HMDB
US5650440 Patent
YMDB01584 YMDB
View more database links
Registry Numbers Types Sources
1723817 Reaxys Registry Number Reaxys
2306-22-1 CAS Registry Number KEGG COMPOUND
2306-22-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
13160012 PubMed citation Europe PMC
14470458 PubMed citation Europe PMC
17439666 PubMed citation Europe PMC
21871058 PubMed citation Europe PMC
6145530 PubMed citation Europe PMC
7408203 PubMed citation Europe PMC
Last Modified
23 October 2015