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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:22:50 UTC
Update Date2022-03-07 03:17:45 UTC
HMDB IDHMDB0060466
Secondary Accession Numbers
  • HMDB60466
Metabolite Identification
Common NameD-4-Hydroxy-2-oxoglutarate
DescriptionD-4-Hydroxy-2-oxoglutarate, also known as D-4-hydroxy-2-ketoglutaric acid, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. D-4-Hydroxy-2-oxoglutarate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-4-Hydroxy-2-oxoglutarate exists in all living organisms, ranging from bacteria to humans. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
Structure
Thumb
Synonyms
ValueSource
(R)-2-Hydroxy-4-ketopentanedioic acidChEBI
(R)-2-Hydroxy-4-oxopentanedioic acidChEBI
D-4-Hydroxy-2-ketoglutaric acidChEBI
(R)-2-Hydroxy-4-oxopentanedioateKegg
(R)-2-Hydroxy-4-ketopentanedioateGenerator
D-4-Hydroxy-2-ketoglutarateGenerator
D-4-Hydroxy-2-oxoglutaric acidGenerator
Chemical FormulaC5H6O6
Average Molecular Weight162.0975
Monoisotopic Molecular Weight162.016437924
IUPAC Name(2R)-2-hydroxy-4-oxopentanedioic acid
Traditional NameD-4-hydroxy-2-oxoglutaric acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(CC(=O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H6O6/c6-2(4(8)9)1-3(7)5(10)11/h2,6H,1H2,(H,8,9)(H,10,11)/t2-/m1/s1
InChI KeyWXSKVKPSMAHCSG-UWTATZPHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-keto acids and derivatives
Alternative Parents
Substituents
  • Gamma-keto acid
  • Short-chain keto acid
  • Alpha-hydroxy acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID389695
KEGG Compound IDC05946
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440853
PDB IDNot Available
ChEBI ID4083
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
Reactions
4-Hydroxy-L-glutamic acid + Oxoglutaric acid → D-4-Hydroxy-2-oxoglutarate + Glutamic aciddetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
Reactions
4-Hydroxy-L-glutamic acid + Oxoglutaric acid → D-4-Hydroxy-2-oxoglutarate + Glutamic aciddetails