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Record Information
Version	2.0
Creation Date	2012-05-31 14:04:00 -0600
Update Date	2015-06-03 15:54:41 -0600
Secondary Accession Numbers	ECMDB04062
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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa1e57e04> Close
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Keto acids and derivatives
Sub Class	Medium-chain keto acids and derivatives
Direct Parent	Medium-chain keto acids and derivatives
Alternative Parents	Beta hydroxy acids and derivatives Monosaccharides Beta-hydroxy ketones Alpha-keto acids and derivatives Acyloins Alpha-hydroxy ketones Secondary alcohols Polyols Monocarboxylic acids and derivatives Carboxylic acids Primary alcohols Organic oxides Hydrocarbon derivatives Organic anions
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 Framework	Aliphatic acyclic compounds
External Descriptors	2-oxo monocarboxylic acid anion (CHEBI:11449 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 173 g/L ALOGPS logP -1.1 ALOGPS logP -2 ChemAxon logS -0.08 ALOGPS pKa (Strongest Acidic) 2.52 ChemAxon pKa (Strongest Basic) -3.3 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 134.96 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 47.65 m³·mol⁻¹ ChemAxon Polarizability 15.11 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	2,5-Diketo-D-gluconate + Hydrogen ion + NADPH >2 -Dehydro-L-gulonate + NADP 2,5-Diketo-D-gluconate + Hydrogen ion + NADH > 5-Keto-D-gluconate + NAD 2,5-Diketo-D-gluconate + Hydrogen ion + NADPH > 5-Keto-D-gluconate + NADP Hydrogen ion + NADPH + 2,5-Diketo-D-gluconate <> 2-Dehydro-D-gluconate + NADP 2,5-Diketo-D-gluconate + NAD(P)H + Hydrogen ion > 2-keto-L-gulonate + NAD(P)<sup>+</sup> Hydrogen ion + 2,5-Diketo-D-gluconate + NADPH <> 5-Keto-D-gluconate + NADP NADP <> 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion 2-Dehydro-D-gluconate + NADP <> 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion + NADPH > NADP + 5-Keto-D-gluconate + 5-Keto-D-gluconate 2,5-Diketo-D-gluconate + Hydrogen ion + NADPH + NADPH > NADP + 2-Keto-L-gluconate + 2-Dehydro-D-gluconate NADP <>2 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion 2 2-Dehydro-D-gluconate + NADP <>2 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion
SMPDB Pathways:	ketogluconate metabolism PW002003
KEGG Pathways:	Not Available
EcoCyc Pathways:	ketogluconate metabolism KETOGLUCONMET-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0006-0900000000-66697df72cf11dbf7f41 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03ec-7900000000-97ebe6ed711475246178 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03dl-9200000000-a963788665da60d07e0a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00ko-7900000000-eb51687ff97b29540276 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-052r-9400000000-5a948ab5e28d4d5a185b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-60c5fc89ff115a2f2c2d View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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 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
Links
External Links:	Resource Link CHEBI ID 11449 HMDB ID Not Available Pubchem Compound ID 9548631 Kegg ID C02780 ChemSpider ID 7827554 Wikipedia ID Not Available BioCyc ID 25-DIDEHYDRO-D-GLUCONATE EcoCyc ID 25-DIDEHYDRO-D-GLUCONATE

Enzymes