Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2021-09-14 15:20:03 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 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. In humans, 4-hydroxy-2-oxoglutaric acid is involved in the metabolic disorder called hyperornithinemia with gyrate atrophy (hoga). 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. 4-Hydroxy-2-oxoglutaric acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 4-Hydroxy-2-oxoglutaric acid.
Structure
Data?1582752227
Synonyms
ValueSource
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
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

Process

Naturally occurring process

Physical Properties
StateSolid
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
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.94931661259
DarkChem[M-H]-130.66931661259
DeepCCS[M+H]+126.01830932474
DeepCCS[M-H]-122.16930932474
DeepCCS[M-2H]-159.70630932474
DeepCCS[M+Na]+135.07330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-2-oxoglutaric acidOC(CC(=O)C(O)=O)C(O)=O2357.1Standard polar33892256
4-Hydroxy-2-oxoglutaric acidOC(CC(=O)C(O)=O)C(O)=O1311.3Standard non polar33892256
4-Hydroxy-2-oxoglutaric acidOC(CC(=O)C(O)=O)C(O)=O1462.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-2-oxoglutaric acid,1TMS,isomer #1C[Si](C)(C)OC(CC(=O)C(=O)O)C(=O)O1504.7Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C(=O)CC(O)C(=O)O1479.1Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,1TMS,isomer #3C[Si](C)(C)OC(=O)C(O)CC(=O)C(=O)O1523.1Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,1TMS,isomer #4C[Si](C)(C)OC(=CC(O)C(=O)O)C(=O)O1600.9Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CC(O[Si](C)(C)C)C(=O)O1591.7Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C(CC(=O)C(=O)O)O[Si](C)(C)C1608.0Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,2TMS,isomer #3C[Si](C)(C)OC(=CC(O[Si](C)(C)C)C(=O)O)C(=O)O1700.3Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,2TMS,isomer #4C[Si](C)(C)OC(=O)C(=O)CC(O)C(=O)O[Si](C)(C)C1591.5Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,2TMS,isomer #5C[Si](C)(C)OC(=O)C(=CC(O)C(=O)O)O[Si](C)(C)C1627.1Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,2TMS,isomer #6C[Si](C)(C)OC(=O)C(O)C=C(O[Si](C)(C)C)C(=O)O1674.1Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1693.9Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,3TMS,isomer #2C[Si](C)(C)OC(=O)C(=CC(O[Si](C)(C)C)C(=O)O)O[Si](C)(C)C1717.4Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,3TMS,isomer #3C[Si](C)(C)OC(=O)C(C=C(O[Si](C)(C)C)C(=O)O)O[Si](C)(C)C1775.2Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,3TMS,isomer #4C[Si](C)(C)OC(=O)C(=CC(O)C(=O)O[Si](C)(C)C)O[Si](C)(C)C1667.7Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C1756.9Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C1714.2Standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C1694.8Standard polar33892256
4-Hydroxy-2-oxoglutaric acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CC(=O)C(=O)O)C(=O)O1769.6Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC(O)C(=O)O1744.8Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(O)CC(=O)C(=O)O1809.3Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CC(O)C(=O)O)C(=O)O1854.1Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC(O[Si](C)(C)C(C)(C)C)C(=O)O2058.9Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)C(=O)O)O[Si](C)(C)C(C)(C)C2079.1Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC(O[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O2171.6Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC(O)C(=O)O[Si](C)(C)C(C)(C)C2061.6Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)C(=CC(O)C(=O)O)O[Si](C)(C)C(C)(C)C2108.1Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)C(O)C=C(O[Si](C)(C)C(C)(C)C)C(=O)O2143.7Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2325.1Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=CC(O[Si](C)(C)C(C)(C)C)C(=O)O)O[Si](C)(C)C(C)(C)C2369.4Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O)O[Si](C)(C)C(C)(C)C2428.9Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(=CC(O)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2329.6Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2560.5Semi standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2414.8Standard non polar33892256
4-Hydroxy-2-oxoglutaric acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2235.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-2-oxoglutaric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9100000000-86646efd7b91f9c2b26e2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-2-oxoglutaric acid GC-MS (3 TMS) - 70eV, Positivesplash10-03ki-5194000000-f0675d41da8301324b832017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-2-oxoglutaric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxoglutaric acid 10V, Positive-QTOFsplash10-01ot-2900000000-fd2a634c0c83321df9f82015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxoglutaric acid 20V, Positive-QTOFsplash10-002b-6900000000-13f2fbc268a7b1bfe8852015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxoglutaric acid 40V, Positive-QTOFsplash10-05i4-9100000000-ca03fcf215517c7092452015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxoglutaric acid 10V, Negative-QTOFsplash10-03di-2900000000-7b0bd810c920b58daa792015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxoglutaric acid 20V, Negative-QTOFsplash10-00xs-9600000000-6734be382dda3c66592a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxoglutaric acid 40V, Negative-QTOFsplash10-00dm-9000000000-ff1b08ca89e9629f09122015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxoglutaric acid 10V, Positive-QTOFsplash10-00kb-6900000000-661f455fd4b6e8da0c822021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxoglutaric acid 20V, Positive-QTOFsplash10-00dm-9100000000-b9bce861b26dd80013322021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxoglutaric acid 40V, Positive-QTOFsplash10-0006-9000000000-a0587223ecf12202531f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxoglutaric acid 10V, Negative-QTOFsplash10-014j-5900000000-30fe0301167b3cea2c0b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxoglutaric acid 20V, Negative-QTOFsplash10-006t-9000000000-5bbf6f8b15e9a3af889b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxoglutaric acid 40V, Negative-QTOFsplash10-0006-9000000000-e7768f77ba36e7e3743b2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDNot Available
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