Showing metabocard for 2-Hydroxyglutarate (BMDB0062055)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-06-25 21:47:12 UTC
Update Date2020-05-11 19:54:18 UTC
BMDB IDBMDB0062055
Secondary Accession Numbers
  • BMDB62055
Metabolite Identification
Common Name2-Hydroxyglutarate
Description2-Hydroxyglutaric acid, also known as alpha-hydroxyglutarate, belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms. 2-Hydroxyglutaric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Hydroxyglutaric acid exists in all living species, ranging from bacteria to humans. 2-Hydroxyglutaric acid is a potentially toxic compound. 2-Hydroxyglutaric acid has been found to be associated with several diseases known as eosinophilic esophagitis, deafness, onychodystrophy, osteodystrophy, mental retardation, and seizures syndrome, 3-hydroxyacyl-coa dehydrogenase deficiency, and colorectal cancer; also 2-hydroxyglutaric acid has been linked to the inborn metabolic disorders including l-2-hydroxyglutaric aciduria.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
alpha-Hydroxyglutaric acidChEBI
alpha-HydroxyglutarateKegg
a-HydroxyglutarateGenerator
a-Hydroxyglutaric acidGenerator
Α-hydroxyglutarateGenerator
Α-hydroxyglutaric acidGenerator
2-Hydroxyglutaric acidGenerator
D-2-HydroxyglutarateHMDB
alpha-Hydroxyglutarate, (D)-isomerHMDB
alpha-Hydroxyglutarate, (DL)-isomerHMDB
alpha-Hydroxyglutarate, (L)-isomerHMDB
alpha-Hydroxyglutarate, disodium saltHMDB
(±)-2-hydroxyglutaric acidHMDB
2,3-Dideoxypentaric acidHMDB
2-Hydroxypentanedioic acidHMDB
DL-2-Hydroxyglutaric acidHMDB
2-HydroxyglutarateGenerator
Chemical FormulaC5H8O5
Average Molecular Weight148.114
Monoisotopic Molecular Weight148.037173366
IUPAC Name2-hydroxypentanedioic acid
Traditional Name2-hydroxyglutaric acid
CAS Registry Number2889-31-8
SMILES
OC(CCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)
InChI KeyHWXBTNAVRSUOJR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassShort-chain hydroxy acids and derivatives
Direct ParentShort-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Fatty acid
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1ALOGPS
logP-0.82ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity29.63 m³·mol⁻¹ChemAxon
Polarizability12.97 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Brain
  • Liver
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
HMDB IDHMDB0059655
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID42
KEGG Compound IDC02630
BioCyc ID2-HYDROXYGLUTARIC_ACID
BiGG IDNot Available
Wikipedia LinkAlpha-Hydroxyglutaric_acid
METLIN IDNot Available
PubChem Compound43
PDB IDNot Available
ChEBI ID17084
References
Synthesis ReferenceKobayashi, Hidehiko; Yamaguchi, Koretaka; Yamashita, Takeshi. a-Hydroxyglutaric acid from glutamic acid. Jpn. Tokkyo Koho (1968), 3 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. [PubMed:5409465 ]