Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000592
Identification
Name: 2,5-Diketo-D-gluconate
Description:2,5-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
Average Molecular Weight: 191.1156
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Hydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Medium-chain keto acid
  • Beta-hydroxy acid
  • Monosaccharide
  • Keto acid
  • Hydroxy acid
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Alpha-keto acid
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • Carboxylic acid salt
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility173.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity47.65 m3·mol-1ChemAxon
Polarizability15.11 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: 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