Record Information
Version2.0
Creation Date2012-05-31 14:20:36 -0600
Update Date2015-09-17 15:41:46 -0600
Secondary Accession Numbers
  • ECMDB11731
Identification
Name:5-Keto-D-gluconate
Description5-Keto-D-gluconate is metabolized from glucose in certain bacterial species. It is an intermediate in L-idonate degradation and ketogluconate metabolism. 5-Keto-D-gluconate 5-reductase catalyzes the reversible reduction of 5-ketogluconate to D-gluconate. This is the second reaction of the L-idonate catabolic pathway after uptake of L-idonate into the cell. The enzyme specifically reduces 5-ketogluconate using either NADH or NADPH. The enzyme is also specific for D-gluconate oxidation using NADP as the coenzyme, NAD does not serve as a coenzyme.
Structure
Thumb
Synonyms:
  • 5-Dehydro-D-gluconate
  • 5-Dehydro-D-gluconic acid
  • 5-Dehydrogluconate
  • 5-Dehydrogluconic acid
  • 5-k-Gluconate
  • 5-k-Gluconic acid
  • 5-Keto-D-gluconate
  • 5-Keto-D-gluconic acid
  • 5-Ketogluconate
  • 5-Ketogluconic acid
  • 5K-Gluconate
  • 5K-Gluconic acid
  • D-tagaturonate
  • D-tagaturonic acid
  • Hex-5-ulosonate
  • Hex-5-ulosonic acid
  • Tagaturonate
  • Tagaturonic acid
Chemical Formula:C6H10O7
Weight:Average: 194.1394
Monoisotopic: 194.042652674
InChI Key:IZSRJDGCGRAUAR-UHFFFAOYSA-N
InChI:InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h3-5,7,9-11H,1H2,(H,12,13)
CAS number:3470-36-8
IUPAC Name:(2R,3S,4S)-2,3,4,6-tetrahydroxy-5-oxohexanoic acid
Traditional IUPAC Name:5-dehydrogluconate
SMILES:OCC(=O)C(O)C(O)C(O)C(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
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Acyloin
  • Alpha-hydroxy acid
  • Beta-hydroxy ketone
  • Monosaccharide
  • Fatty acyl
  • Fatty acid
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility112 g/LALOGPS
logP-2.5ALOGPS
logP-2.9ChemAxon
logS-0.24ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area135.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.43 m³·mol⁻¹ChemAxon
Polarizability16.32 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
ketogluconate metabolismPW002003 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Pentose and glucuronate interconversions ec00040
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-2900000000-0af971abb8407c7b640cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9400000000-31b04757e6b9cbdbd7f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-f97908d555d85b4bc6e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05n0-9800000000-7c97e2503675894394d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9400000000-7961255e83b6d2f38bfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-b1bbfcb7ec35db5cfe1eView in MoNA
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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17426
HMDB IDHMDB11731
Pubchem Compound ID157
Kegg IDC01062
ChemSpider ID152
Wikipedia IDNot Available
BioCyc ID5-DEHYDROGLUCONATE
EcoCyc ID5-DEHYDROGLUCONATE

Enzymes

General function:
Involved in oxidation-reduction process
Specific function:
D-altronate + NAD(+) = D-tagaturonate + NADH
Gene Name:
uxaB
Uniprot ID:
P0A6L7
Molecular weight:
54808
Reactions
D-altronate + NAD(+) = D-tagaturonate + NADH.
General function:
Involved in glucuronate isomerase activity
Specific function:
D-glucuronate = D-fructuronate
Gene Name:
uxaC
Uniprot ID:
P0A8G3
Molecular weight:
53987
Reactions
D-glucuronate = D-fructuronate.
D-galacturonate = D-tagaturonate.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes a reversible reduction of 5-ketoglutanate to form D-gluconate. Dependent on NADP, almost inactive with NAD
Gene Name:
idnO
Uniprot ID:
P0A9P9
Molecular weight:
27563
Reactions
D-gluconate + NAD(P)(+) = 5-dehydro-D-gluconate + NAD(P)H.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Can also reduce 2,5-diketo-D-gluconate (25DKG) to 5-keto-D- gluconate (5KDG), 2-keto-D-gluconate (2KDG) to D-gluconate, and 2- keto-L-gulonate (2KLG) to L-idonate (IA), but it is not its physiological function. Inactive towards 2-oxoglutarate, oxaloacetate, pyruvate, 5-keto-D-gluconate, D-fructose and L- sorbose. Activity with NAD is very low
Gene Name:
ghrB
Uniprot ID:
P37666
Molecular weight:
35395
Reactions
Glycolate + NADP(+) = glyoxylate + NADPH.
D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H.
D-gluconate + NADP(+) = 2-dehydro-D-gluconate + NADPH.
General function:
Involved in zinc ion binding
Specific function:
Catalyzes the NADH/NADPH-dependent oxidation of L- idonate to 5-ketogluconate (5KG)
Gene Name:
idnD
Uniprot ID:
P39346
Molecular weight:
37146
Reactions
L-idonate + NAD(P)(+) = 5-dehydrogluconate + NAD(P)H.
General function:
Involved in zinc ion binding
Specific function:
Putative L-galactonate oxidoreductase that is required for growth on L-galactonate as the sole carbon source
Gene Name:
yjjN
Uniprot ID:
P39400
Molecular weight:
36448

Transporters

General function:
Involved in gluconate transmembrane transporter activity
Specific function:
Transports L-idonate, D-gluconate and 5-keto-D- gluconate, from the periplasm across the inner membrane
Gene Name:
idnT
Uniprot ID:
P39344
Molecular weight:
46041
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368