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Record Information
Version	2.0
Creation Date	2012-05-31 14:22:44 -0600
Update Date	2015-06-03 17:19:07 -0600
Secondary Accession Numbers	ECMDB20011
Identification
Name:	(4S)-4,6-Dihydroxy-2,5-dioxohexanoate
Description	(4S)-4,6-Dihydroxy-2,5-dioxohexanoate (2,5-Diketo-3-deoxy-D-gluconate or 3-Deoxy-D-glycero-2,5-hexodiulosonate) is involved in pentose and glucuronate interconversions. It is a substrate for 2-dehydro-3-deoxy-D-gluconate 5-dehydrogenase. This enzyme catalyzes the reduction of 2,5-diketo-3-deoxygluconate (DKII or 4,6-dihydroxy-2,5-dioxohexanoate) into 2-keto-3-deoxygluconate (KDG or 2-dehydro-3-deoxygluconate) with a concomitant oxidation of NADH. It is also a substrate for 4-deoxy-L-threo-5-hexosulose-uronate ketol-isomerase. This enzyme catalyzes the isomerization of 5-dehydro-4-deoxy-D-glucuronate to 3-deoxy-D-glycero-2,5-hexodiulosonate.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xad4d4b28> Close
Synonyms:	(4S)-4,6-dihydroxy-2,5-dioxohexanoate (4S)-4,6-dihydroxy-2,5-dioxohexanoic acid 2,5-Diketo-3-deoxy-D-gluconate 2,5-Diketo-3-deoxy-D-gluconic acid 3-Deoxy-D-glycero-2,5-hexodiulosonate 3-Deoxy-D-glycero-2,5-hexodiulosonic acid 3-Deoxy-D-glycero-hexo-2,5-diulosonate 3-Deoxy-D-glycero-hexo-2,5-diulosonic acid
Chemical Formula:	C6H8O6
Weight:	Average: 176.1241 Monoisotopic: 176.032087988
InChI Key:	IBGYNIRCYXIAON-VKHMYHEASA-N
InChI:	InChI=1S/C6H8O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,7-8H,1-2H2,(H,11,12)/t3-/m0/s1
CAS number:	Not Available
IUPAC Name:	(4S)-4,6-dihydroxy-2,5-dioxohexanoic acid
Traditional IUPAC Name:	2,5-diketo-3-deoxy-D-gluconate
SMILES:	[H][C@](O)(CC(=O)C(O)=O)C(=O)CO
Chemical Taxonomy
Description	belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Keto acids and derivatives
Sub Class	Medium-chain keto acids and derivatives
Direct Parent	Medium-chain keto acids and derivatives
Alternative Parents	Monosaccharides Beta-hydroxy ketones Alpha-keto acids and derivatives Acyloins Alpha-hydroxy ketones Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Primary alcohols Organic oxides Hydrocarbon derivatives
Substituents	Medium-chain keto acid Acyloin Alpha-keto acid Beta-hydroxy ketone Monosaccharide Alpha-hydroxy ketone Secondary alcohol Ketone Carboxylic acid Carboxylic acid derivative Monocarboxylic acid or derivatives Primary alcohol Alcohol Carbonyl group Organic oxygen compound Hydrocarbon derivative Organic oxide Organooxygen compound Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	dioxo monocarboxylic acid (CHEBI:15623 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 66.7 g/L ALOGPS logP -1.4 ALOGPS logP -1.3 ChemAxon logS -0.42 ALOGPS pKa (Strongest Acidic) 2.74 ChemAxon pKa (Strongest Basic) -3.3 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 111.9 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 35.47 m³·mol⁻¹ ChemAxon Polarizability 14.89 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:	2-Keto-3-deoxy-D-gluconic acid + NAD <> (4S)-4,6-Dihydroxy-2,5-dioxohexanoate + NADH + Hydrogen ion 5-Dehydro-4-deoxy-D-glucuronate <> (4S)-4,6-Dihydroxy-2,5-dioxohexanoate 2-Keto-3-deoxy-D-gluconic acid + NAD > (4S)-4,6-Dihydroxy-2,5-dioxohexanoate + NADH 5-Dehydro-4-deoxy-D-glucuronate > (4S)-4,6-Dihydroxy-2,5-dioxohexanoate
SMPDB Pathways:	Collection of Reactions without pathways PW001891
KEGG Pathways:	Pentose and glucuronate interconversions ec00040
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a6r-1900000000-e5f902336ca480e75655 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a4u-6900000000-07b7eea4bbc3a4cd1976 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4l-9200000000-c942a7d5e812325a0079 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-056r-3900000000-74611e36a0771d4c94cc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0abj-9600000000-80ec4c6b80d2c6bc4ba5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9100000000-ca64c9bfb85ab21c41a9 View in MoNA 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 1D NMR 1H 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15623 HMDB ID Not Available Pubchem Compound ID 440303 Kegg ID C04349 ChemSpider ID 389277 Wikipedia ID Not Available BioCyc ID CPD-1945 EcoCyc ID CPD-1945

Enzymes