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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2020-02-26 21:23:47 UTC
HMDB IDHMDB0002070
Secondary Accession Numbers
  • HMDB0001479
  • HMDB01479
  • HMDB02070
Metabolite Identification
Common Name4-Hydroxy-2-oxoglutaric acid
Description4-Hydroxy-2-oxoglutaric acid, also known as 4-hydroxy-2-ketoglutarate or 2-hydroxy-4-oxopentanedioate, 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. 4-Hydroxy-2-oxoglutaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxy-2-oxoglutaric acid exists in all living species, ranging from bacteria to humans. 4-hydroxy-2-oxoglutaric acid and L-aspartic acid can be biosynthesized from 4-hydroxy-L-glutamic acid and oxalacetic acid; which is mediated by the enzyme aspartate aminotransferase, cytoplasmic. In humans, 4-hydroxy-2-oxoglutaric acid is involved in the metabolic disorder called hyperprolinemia type II. An oxo dicarboxylic acid comprising glutaric acid having oxo- and hydroxy substituents at the 2- and 4-positions respectively.
Structure
Data?1582752227
Synonyms
ValueSource
4-Hydroxy-2-oxoglutarateGenerator
(+/-)-2-hydroxy-4-oxopentanedioateHMDB
(+/-)-2-hydroxy-4-oxopentanedioic acidHMDB
2-Hydroxy-4-oxopentanedioateHMDB
2-Hydroxy-4-oxopentanedioic acidHMDB
2-Keto-4-hydroxyglutarateHMDB
2-oxo-4-HydroxyglutarateHMDB
4-Hydroxy-2-ketoglutarateHMDB
D-4-Hydroxy-2-ketoglutarateHMDB
2-Keto-4-hydroxyglutarate, (+-)-isomerHMDB
Chemical FormulaC5H6O6
Average Molecular Weight162.0975
Monoisotopic Molecular Weight162.016437924
IUPAC Name2-hydroxy-4-oxopentanedioic acid
Traditional Name4-hydroxy-2-oxoglutaric acid
CAS Registry Number1187-99-1
SMILES
OC(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)
InChI KeyWXSKVKPSMAHCSG-UHFFFAOYSA-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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility69.8 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.22 m³·mol⁻¹ChemAxon
Polarizability12.76 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9100000000-86646efd7b91f9c2b26eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03ki-5194000000-f0675d41da8301324b83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-2900000000-fd2a634c0c83321df9f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-6900000000-13f2fbc268a7b1bfe885Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i4-9100000000-ca03fcf215517c709245Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-7b0bd810c920b58daa79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-9600000000-6734be382dda3c66592aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dm-9000000000-ff1b08ca89e9629f0912Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
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 IDFDB022830
KNApSAcK IDNot Available
Chemspider ID579
KEGG Compound IDC01127
BioCyc IDNot Available
BiGG ID36868
Wikipedia LinkNot Available
METLIN ID6471
PubChem Compound599
PDB IDNot Available
ChEBI ID30923
Food Biomarker OntologyNot Available
VMH ID4H2OGLT
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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
General function:
Not Available
Specific function:
Catalyzes the final step in the metabolic pathway of hydroxyproline (Probable).
Gene Name:
HOGA1
Uniprot ID:
Q86XE5
Molecular weight:
17953.475
Reactions
4-Hydroxy-2-oxoglutaric acid → Pyruvic acid + Glyoxylic aciddetails