Record Information
Version2.0
Creation Date2012-05-31 14:04:00 -0600
Update Date2015-06-03 15:54:41 -0600
Secondary Accession Numbers
  • ECMDB04062
Identification
Name:2,5-Diketo-D-gluconate
Description2,5-Diketo-D-gluconate is an intermediate in the synthesis of ascorbic acid. It is a substrate for the enzyme 2,5-diketo-D-gluconic acid reductase B. This enzyme catalyzes the reduction of 2,5-diketo-D-gluconic acid (25DKG) to 2-keto-L-gulonic acid (2KLG) with the following reaction: 2-dehydro-D-gluconate + NADP+ = 2,5-didehydro-D-gluconate + NADPH.
Structure
Thumb
Synonyms:
  • 2,5-Didehydro-D-gluconate
  • 2,5-Didehydro-D-gluconic acid
  • 2,5-diketo-D-gluconate
  • 2,5-Diketo-D-gluconic acid
  • 2,5-Diketogluconate
  • 2,5-Diketogluconic acid
  • 2-Dehydro-L-idonate
  • 2-Dehydro-L-idonic acid
  • D-Threo-hexo-2,5-diulosonate
  • D-Threo-hexo-2,5-diulosonic acid
Chemical Formula:C6H7O7
Weight:Average: 191.1156
Monoisotopic: 191.019177578
InChI Key:RXMWXENJQAINCC-DMTCNVIQSA-M
InChI:InChI=1S/C6H8O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h3-4,7,9-10H,1H2,(H,12,13)/p-1/t3-,4+/m1/s1
CAS number:53736-12-2
IUPAC Name:(3S,4S)-3,4,6-trihydroxy-2,5-dioxohexanoate
Traditional IUPAC Name:2,5-diketo-D-gluconate
SMILES:[H][C@@](O)(C(=O)CO)[C@]([H])(O)C(=O)C([O-])=O
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
  • Beta-hydroxy acid
  • Acyloin
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Hydroxy acid
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Primary alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • 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 Solubility173 g/LALOGPS
logP-1.1ALOGPS
logP-2ChemAxon
logS-0.08ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area134.96 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity47.65 m³·mol⁻¹ChemAxon
Polarizability15.11 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:Not Available
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-66697df72cf11dbf7f41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ec-7900000000-97ebe6ed711475246178View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9200000000-a963788665da60d07e0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ko-7900000000-eb51687ff97b29540276View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-9400000000-5a948ab5e28d4d5a185bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-60c5fc89ff115a2f2c2dView 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
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID11449
HMDB IDNot Available
Pubchem Compound ID9548631
Kegg IDC02780
ChemSpider ID7827554
Wikipedia IDNot Available
BioCyc ID25-DIDEHYDRO-D-GLUCONATE
EcoCyc ID25-DIDEHYDRO-D-GLUCONATE

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the reduction of 2,5-diketo-D-gluconic acid (25DKG) to 2-keto-L-gulonic acid (2KLG)
Gene Name:
dkgB
Uniprot ID:
P30863
Molecular weight:
29437
Reactions
2-dehydro-D-gluconate + NADP(+) = 2,5-didehydro-D-gluconate + NADPH.
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 oxidoreductase activity
Specific function:
Catalyzes the reduction of 2,5-diketo-D-gluconic acid (25DKG) to 2-keto-L-gulonic acid (2KLG). It is also capable of stereoselective -keto ester reductions on ethyl acetoacetate and other 2-substituted derivatives
Gene Name:
dkgA
Uniprot ID:
Q46857
Molecular weight:
31109
Reactions
2-dehydro-D-gluconate + NADP(+) = 2,5-didehydro-D-gluconate + NADPH.