Record Information
Version2.0
Creation Date2012-05-31 14:22:44 -0600
Update Date2015-06-03 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
Thumb
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility66.7 g/LALOGPS
logP-1.4ALOGPS
logP-1.3ChemAxon
logS-0.42ALOGPS
pKa (Strongest Acidic)2.74ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.47 m³·mol⁻¹ChemAxon
Polarizability14.89 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Collection of Reactions without pathwaysPW001891 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Pentose and glucuronate interconversions ec00040
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-1900000000-e5f902336ca480e75655View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4u-6900000000-07b7eea4bbc3a4cd1976View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9200000000-c942a7d5e812325a0079View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-3900000000-74611e36a0771d4c94ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abj-9600000000-80ec4c6b80d2c6bc4ba5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-ca64c9bfb85ab21c41a9View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView 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
External Links:
ResourceLink
CHEBI ID15623
HMDB IDNot Available
Pubchem Compound ID440303
Kegg IDC04349
ChemSpider ID389277
Wikipedia IDNot Available
BioCyc IDCPD-1945
EcoCyc IDCPD-1945

Enzymes

General function:
Involved in 2-deoxy-D-gluconate 3-dehydrogenase activity
Specific function:
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
Gene Name:
kduD
Uniprot ID:
P37769
Molecular weight:
27070
Reactions
2-dehydro-3-deoxy-D-gluconate + NAD(+) = (4S)-4,6-dihydroxy-2,5-dioxohexanoate + NADH.
General function:
Involved in 4-deoxy-L-threo-5-hexosulose-uronate ketol-isomerase activity
Specific function:
4-deoxy-L-threo-5-hexosulose uronate = 3- deoxy-D-glycero-2,5-hexodiulosonate
Gene Name:
kduI
Uniprot ID:
Q46938
Molecular weight:
31076
Reactions
4-deoxy-L-threo-5-hexosulose uronate = 3-deoxy-D-glycero-2,5-hexodiulosonate.