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2-Deoxygluconate (M2MDB000583)

Record Information
Version2.0
Creation Date2012-05-31 14:03:32 -0600
Update Date2015-06-03 15:54:40 -0600
Secondary Accession Numbers
  • ECMDB04050
Identification
Name:2-Deoxygluconate
Description2-deoxygluconate is a hexose. It is a substrate for 2-deoxygluconate dehydrogenase (kduD or EC 1.1.1.125) and participates in the following reaction: 2-deoxy-D-gluconate + NAD+ = 3-dehydro-2-deoxy-D-gluconate + NADH + H+
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-Deoxy-D-gluconate
  • 2-Deoxy-D-gluconic acid
  • 2-Deoxygluconate
  • 2-Deoxygluconic acid
  • De-O-gluconate
  • De-O-gluconic acid
Chemical Formula:C6H11O6
Weight:Average: 179.1479
Monoisotopic: 179.055563084
InChI Key:PALQXFMLVVWXFD-UHFFFAOYSA-M
InChI:InChI=1S/C6H12O6/c7-2-4(9)6(12)3(8)1-5(10)11/h3-4,6-9,12H,1-2H2,(H,10,11)/p-1
CAS number:3442-69-1
IUPAC Name:3,4,5,6-tetrahydroxyhexanoate
Traditional IUPAC Name:3,4,5,6-tetrahydroxyhexanoate
SMILES:OCC(O)C(O)C(O)CC([O-])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Beta-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • 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 Solubility812 g/LALOGPS
logP-2ALOGPS
logP-2.7ChemAxon
logS0.61ALOGPS
pKa (Strongest Acidic)3.99ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area121.05 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity47.77 m³·mol⁻¹ChemAxon
Polarizability15.69 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
NAD + 2-Deoxygluconate <> Hydrogen ion + NADH + 3-Dehydro-2-deoxy-D-gluconate
2-Deoxygluconate + NAD > 3-Dehydro-2-deoxy-D-gluconate + NADH + Hydrogen ion
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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015a-1900000000-3fe0d7399c1513892a0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0292-6900000000-f2f359ad6788b98db32bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-9100000000-1fcac427916301786043View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-3900000000-f92cc3559f7cae2a6b2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07vi-9800000000-ea599acf28668bbce510View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9200000000-a979c2b094ae4106ca91View 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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16138
HMDB IDNot Available
Pubchem Compound ID22134426
Kegg IDC02782
ChemSpider ID11178726
Wikipedia IDNot Available
BioCyc IDDE-O-GLUCONATE
EcoCyc IDDE-O-GLUCONATE

Enzymes

Protein Details
1. 2-dehydro-3-deoxy-D-gluconate 5-dehydrogenase
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.