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Record Information
Version	2.0
Creation Date	2012-05-31 14:29:20 -0600
Update Date	2015-06-03 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	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xb011e210> Close
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
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Keto acids and derivatives
Sub Class	Gamma-keto acids and derivatives
Direct Parent	Gamma-keto acids and derivatives
Alternative Parents	Short-chain keto acids and derivatives Dicarboxylic acids and derivatives Beta-hydroxy ketones Alpha-keto acids and derivatives Alpha hydroxy acids and derivatives Alpha-hydroxy ketones Secondary alcohols Carboxylic acids Organic oxides Hydrocarbon derivatives
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 Framework	Aliphatic acyclic compounds
External Descriptors	4-hydroxy-2-oxoglutaric acid (CHEBI:4083 )
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 69.8 g/L ALOGPS logP -1.1 ALOGPS logP -0.82 ChemAxon logS -0.37 ALOGPS pKa (Strongest Acidic) 2.45 ChemAxon pKa (Strongest Basic) -3.9 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 111.9 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 30.22 m³·mol⁻¹ ChemAxon Polarizability 12.94 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	D-4-Hydroxy-2-oxoglutarate <> Pyruvic acid + Glyoxylic acid L-erythro-4-Hydroxyglutamate + alpha-Ketoglutarate <> D-4-Hydroxy-2-oxoglutarate + L-Glutamate
SMPDB Pathways:	Not Available
KEGG Pathways:	Arginine and proline metabolism ec00330
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-006x-9000000000-2c6c794011a817bacec0 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive splash10-044r-8293000000-95ba160f1f36438fedfd View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-01ot-2900000000-fd2a634c0c83321df9f8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-002b-6900000000-13f2fbc268a7b1bfe885 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-05i4-9100000000-ca03fcf215517c709245 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-2900000000-7b0bd810c920b58daa79 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00xs-9600000000-6734be382dda3c66592a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00dm-9000000000-ff1b08ca89e9629f0912 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00kb-6900000000-661f455fd4b6e8da0c82 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00dm-9100000000-b9bce861b26dd8001332 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-a0587223ecf12202531f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-014j-5900000000-30fe0301167b3cea2c0b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-006t-9000000000-5bbf6f8b15e9a3af889b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9000000000-e7768f77ba36e7e3743b View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
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
Links
External Links:	Resource Link CHEBI ID 4083 HMDB ID HMDB02070 Pubchem Compound ID 440853 Kegg ID C05946 ChemSpider ID 389695 Wikipedia ID Not Available BioCyc ID Not Available

Enzymes