Showing metabocard for Citramalic acid (BMDB0000426)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:30:33 UTC
Update Date2020-05-05 18:39:45 UTC
BMDB IDBMDB0000426
Secondary Accession Numbers
  • BMDB00426
Metabolite Identification
Common NameCitramalic acid
DescriptionCitramalic acid, also known as citramalate or 2-methylmalate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Based on a literature review a significant number of articles have been published on Citramalic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-2-Hydroxy-2-methylsuccinic acidChEBI
2-Hydroxy-2-methylbutanedioic acidChEBI
2-Hydroxy-2-methylsuccinic acidChEBI
2-Methylmalic acidChEBI
alpha-Hydroxypyrotartaric acidChEBI
Citramalic acidsChEBI
(+-)-2-Hydroxy-2-methylsuccinateGenerator
2-Hydroxy-2-methylbutanedioateGenerator
2-Hydroxy-2-methylsuccinateGenerator
2-MethylmalateGenerator
a-HydroxypyrotartarateGenerator
a-Hydroxypyrotartaric acidGenerator
alpha-HydroxypyrotartarateGenerator
Α-hydroxypyrotartarateGenerator
Α-hydroxypyrotartaric acidGenerator
CitramalateGenerator
(b)-2-MethylmalateHMDB
(b)-2-Methylmalic acidHMDB
(b)-CitramalateHMDB
(b)-Citramalic acidHMDB
(R,S)-(b)-CitramalateHMDB
(R,S)-(b)-Citramalic acidHMDB
(R,S)-b-MethylmalateHMDB
(R,S)-b-Methylmalic acidHMDB
(R,S)-beta-MethylmalateHMDB
(R,S)-beta-Methylmalic acidHMDB
2-Deoxy-3-C-methyltetrarateHMDB
2-Deoxy-3-C-methyltetraric acidHMDB
2-Hydroxy-2-methyl-(b)-butanedioateHMDB
2-Hydroxy-2-methyl-(b)-butanedioic acidHMDB
2-Hydroxy-2-methyl-butanedioateHMDB
2-Hydroxy-2-methyl-butanedioic acidHMDB
2-Methyl-(b)-malateHMDB
2-Methyl-(b)-malic acidHMDB
DL-CitramalateHMDB
DL-Citramalic acidHMDB
Citramalate, (+-)-isomerHMDB
Citramalate, (R)-isomerHMDB
Citramalate, (S)-isomerHMDB
alpha-MethylmalateHMDB
(R)-2-Hydroxy-2-methylbutanedioateHMDB
Citramalic acidKEGG
Chemical FormulaC5H8O5
Average Molecular Weight148.114
Monoisotopic Molecular Weight148.037173366
IUPAC Name2-hydroxy-2-methylbutanedioic acid
Traditional Namecitramalate, (+-)-
CAS Registry Number597-44-4
SMILES
CC(O)(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)
InChI KeyXFTRTWQBIOMVPK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point107 - 111 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.91ALOGPS
logP-0.68ChemAxon
logS0.3ALOGPS
pKa (Strongest Acidic)3.35ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.59 m³·mol⁻¹ChemAxon
Polarizability12.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Mammary Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000426
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002815
KNApSAcK IDC00001181
Chemspider ID1051
KEGG Compound IDC00815
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5415
PubChem Compound1081
PDB IDNot Available
ChEBI ID15584
References
Synthesis ReferenceBarker, H. A. Chemical synthesis and resolution of (±)-citramalic acid. Biochemical Preparations (1962), 9 25-9.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available