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Showing Compound 4-Hydroxy-2-oxoglutaric acid (FDB022830)

Record Information
Version1.0
Creation date2011-09-21 00:20:16 UTC
Update date2024-11-29 22:26:13 UTC
Primary IDFDB022830
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxy-2-oxoglutaric acid
Description4-Hydroxy-2-oxoglutaric acid, also known as 2-keto-4-hydroxyglutarate, 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 exists in all living species, ranging from bacteria to plants to humans. 4-Hydroxy-2-oxoglutaric acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 4-hydroxy-2-oxoglutaric acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Hydroxy-2-oxoglutaric acid.
CAS Number1187-99-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
4-Hydroxy-2-oxoglutarateGenerator
2-Keto-4-hydroxyglutarateMeSH
2-Keto-4-hydroxyglutarate, (+-)-isomerMeSH
(+/-)-2-hydroxy-4-oxopentanedioateHMDB
(+/-)-2-hydroxy-4-oxopentanedioic acidHMDB
2-Hydroxy-4-oxopentanedioateHMDB
2-Hydroxy-4-oxopentanedioic acidHMDB
2-oxo-4-HydroxyglutarateHMDB
4-Hydroxy-2-ketoglutarateHMDB
D-4-Hydroxy-2-ketoglutarateHMDB
2-hydroxy-4-oxopentanedioatehmdb
2-hydroxy-4-oxopentanedioic acidhmdb
2-keto-4-hydroxyglutaratehmdb
2-Oxo-4-hydroxyglutaratehmdb
4-hydroxy-2-ketoglutaratehmdb
4-hydroxy-2-oxoglutaratehmdb
D-4-hydroxy-2-ketoglutaratehmdb
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
Chemical FormulaC5H6O6
IUPAC name2-hydroxy-4-oxopentanedioic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(CC(=O)C(O)=O)C(O)=O
Average Molecular Weight162.0975
Monoisotopic Molecular Weight162.016437924
Classification
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

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-Hydroxy-2-oxoglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9100000000-86646efd7b91f9c2b26eSpectrum
Predicted GC-MS4-Hydroxy-2-oxoglutaric acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03ki-5194000000-f0675d41da8301324b83Spectrum
Predicted GC-MS4-Hydroxy-2-oxoglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-2900000000-fd2a634c0c83321df9f82015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-6900000000-13f2fbc268a7b1bfe8852015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i4-9100000000-ca03fcf215517c7092452015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-7b0bd810c920b58daa792015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-9600000000-6734be382dda3c66592a2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dm-9000000000-ff1b08ca89e9629f09122015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-6900000000-661f455fd4b6e8da0c822021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-9100000000-b9bce861b26dd80013322021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a0587223ecf12202531f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-5900000000-30fe0301167b3cea2c0b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006t-9000000000-5bbf6f8b15e9a3af889b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e7768f77ba36e7e3743b2021-09-25View Spectrum
NMRNot Available
ChemSpider ID579
ChEMBL IDNot Available
KEGG Compound IDC01127
Pubchem Compound ID599
Pubchem Substance IDNot Available
ChEBI ID30923
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02070
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36868
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Aspartate aminotransferase, cytoplasmicGOT1P17174
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020 map00330
Metabolism and Physiological Effects of Oxalic acidSMP0124875 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference