Record Information
Version2.0
Creation Date2012-05-31 14:29:20 -0600
Update Date2015-06-03 17:19:23 -0600
Secondary Accession Numbers
  • ECMDB20135
Identification
Name:D-4-Hydroxy-2-oxoglutarate
Description:D-4-hydroxy-2-oxoglutarate is a member of the chemical class known as Gamma Keto-Acids and Derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
Structure
Thumb
Synonyms:
  • (+/-)-2-hydroxy-4-oxopentanedioate
  • (+/-)-2-hydroxy-4-oxopentanedioic acid
  • 2-hydroxy-4-oxopentanedioate
  • 2-hydroxy-4-oxopentanedioic acid
  • 2-keto-4-hydroxyglutarate
  • 2-keto-4-Hydroxyglutaric acid
  • 2-Oxo-4-hydroxyglutarate
  • 2-oxo-4-Hydroxyglutaric acid
  • 4-hydroxy-2-ketoglutarate
  • 4-Hydroxy-2-ketoglutaric acid
  • 4-hydroxy-2-oxoglutarate
  • 4-Hydroxy-2-oxoglutaric acid
  • D-4-hydroxy-2-ketoglutarate
  • D-4-Hydroxy-2-ketoglutaric acid
  • D-4-Hydroxy-2-oxoglutaric acid
Chemical Formula:C5H6O6
Weight:Average: 162.0975
Monoisotopic: 162.016437924
InChI Key:WXSKVKPSMAHCSG-UWTATZPHSA-N
InChI: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
CAS number:Not Available
IUPAC Name:(2R)-2-hydroxy-4-oxopentanedioic acid
Traditional IUPAC Name:D-4-hydroxy-2-oxoglutaric acid
SMILES:[H][C@@](O)(CC(=O)C(O)=O)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassKeto 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
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility69.8 mg/mLALOGPS
logP-1.1ALOGPS
logP-0.82ChemAxon
logS-0.37ALOGPS
pKa (Strongest Acidic)2.45ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.22 m3·mol-1ChemAxon
Polarizability12.94 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Arginine and proline metabolism ec00330
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-006x-9000000000-2c6c794011a817bacec0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-044r-8293000000-95ba160f1f36438fedfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-2900000000-fd2a634c0c83321df9f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-6900000000-13f2fbc268a7b1bfe885View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i4-9100000000-ca03fcf215517c709245View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-7b0bd810c920b58daa79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-9600000000-6734be382dda3c66592aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dm-9000000000-ff1b08ca89e9629f0912View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Magrane M, Consortium U: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. Pubmed: 21447597
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID4083
HMDB IDHMDB02070
Pubchem Compound ID440853
Kegg IDC05946
ChemSpider ID389695
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in transferase activity
Specific function:
L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate
Gene Name:
aspC
Uniprot ID:
P00509
Molecular weight:
43573
Reactions
L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate.
General function:
Involved in catalytic activity
Specific function:
4-hydroxy-2-oxoglutarate = pyruvate + glyoxylate
Gene Name:
eda
Uniprot ID:
P0A955
Molecular weight:
22284
Reactions
4-hydroxy-2-oxoglutarate = pyruvate + glyoxylate.
2-dehydro-3-deoxy-D-gluconate 6-phosphate = pyruvate + D-glyceraldehyde 3-phosphate.