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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:

Biological location:

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
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 Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available135.94931661259
DarkChem[M-H]-PredictedNot Available130.66931661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
4-Hydroxy-2-oxoglutaric acid,1TMS,#11504.7236https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,1TMS,#21479.0754https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,1TMS,#31523.0852https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,1TMS,#41600.8501https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,2TMS,#11591.6976https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,2TMS,#21607.9536https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,2TMS,#31700.252https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,2TMS,#41591.5427https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,2TMS,#51627.0717https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,2TMS,#61674.1432https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,3TMS,#11693.8602https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,3TMS,#21717.3529https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,3TMS,#31775.1729https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,3TMS,#41667.7104https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,1TBDMS,#11769.6332https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,1TBDMS,#21744.8203https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,1TBDMS,#31809.25https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,1TBDMS,#41854.0925https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,2TBDMS,#12058.8762https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,2TBDMS,#22079.1072https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,2TBDMS,#32171.6316https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,2TBDMS,#42061.6155https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,2TBDMS,#52108.0808https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,2TBDMS,#62143.7097https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,3TBDMS,#12325.1182https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,3TBDMS,#22369.4373https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,3TBDMS,#32428.8738https://arxiv.org/abs/1905.12712
4-Hydroxy-2-oxoglutaric acid,3TBDMS,#42329.6262https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9100000000-86646efd7b91f9c2b26e2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03ki-5194000000-f0675d41da8301324b832017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-2900000000-fd2a634c0c83321df9f82015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-6900000000-13f2fbc268a7b1bfe8852015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i4-9100000000-ca03fcf215517c7092452015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-7b0bd810c920b58daa792015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-9600000000-6734be382dda3c66592a2015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dm-9000000000-ff1b08ca89e9629f09122015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-6900000000-661f455fd4b6e8da0c822021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-9100000000-b9bce861b26dd80013322021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a0587223ecf12202531f2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-5900000000-30fe0301167b3cea2c0b2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006t-9000000000-5bbf6f8b15e9a3af889b2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e7768f77ba36e7e3743b2021-09-08View 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
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