2.0 2012-05-31 14:04:00 -0600 2015-06-03 15:54:41 -0600 ECMDB04062 M2MDB000592 2,5-Diketo-D-gluconate 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. 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 C6H7O7 191.1156 191.019177578 (3S,4S)-3,4,6-trihydroxy-2,5-dioxohexanoate 2,5-diketo-D-gluconate 53736-12-2 [H][C@@](O)(C(=O)CO)[C@]([H])(O)C(=O)C([O-])=O 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 RXMWXENJQAINCC-DMTCNVIQSA-M Cytosol logp -1.14 ALOGPS logs -0.08 ALOGPS solubility 1.73e+02 g/l ALOGPS logp -2 ChemAxon pka_strongest_acidic 2.52 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (3S,4S)-3,4,6-trihydroxy-2,5-dioxohexanoate ChemAxon average_mass 191.1156 ChemAxon mono_mass 191.019177578 ChemAxon smiles [H][C@@](O)(C(=O)CO)[C@]([H])(O)C(=O)C([O-])=O ChemAxon formula C6H7O7 ChemAxon 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 ChemAxon inchikey RXMWXENJQAINCC-DMTCNVIQSA-M ChemAxon polar_surface_area 134.96 ChemAxon refractivity 47.65 ChemAxon polarizability 15.11 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon ketogluconate metabolism PW002003 Metabolic ketogluconate metabolism KETOGLUCONMET-PWY Specdb::NmrOneD 275458 Specdb::NmrOneD 275459 Specdb::NmrOneD 275460 Specdb::NmrOneD 275461 Specdb::NmrOneD 275462 Specdb::NmrOneD 275463 Specdb::NmrOneD 275464 Specdb::NmrOneD 275465 Specdb::NmrOneD 275466 Specdb::NmrOneD 275467 Specdb::NmrOneD 275468 Specdb::NmrOneD 275469 Specdb::NmrOneD 275470 Specdb::NmrOneD 275471 Specdb::NmrOneD 275472 Specdb::NmrOneD 275473 Specdb::NmrOneD 275474 Specdb::NmrOneD 275475 Specdb::NmrOneD 275476 Specdb::NmrOneD 275477 Specdb::MsMs 26780 Specdb::MsMs 26781 Specdb::MsMs 26782 Specdb::MsMs 33338 Specdb::MsMs 33339 Specdb::MsMs 33340 9548631 7827554 C02780 11449 25-DIDEHYDRO-D-GLUCONATE 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. 21097882 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. 22080510 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. 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 2,5-diketo-D-gluconic acid reductase B P30863 DKGB_ECOLI dkgB http://ecmdb.ca/proteins/P30863.xml Glyoxylate/hydroxypyruvate reductase B P37666 GHRB_ECOLI ghrB http://ecmdb.ca/proteins/P37666.xml 2,5-diketo-D-gluconic acid reductase A Q46857 DKGA_ECOLI dkgA http://ecmdb.ca/proteins/Q46857.xml 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 YIAE1-RXN Hydrogen ion + NADPH + 2,5-Diketo-D-gluconate <> 2-Dehydro-D-gluconate + NADP 1.1.1.274-RXN 2,5-Diketo-D-gluconate + NAD(P)H + Hydrogen ion > 2-keto-L-gulonate + NAD(P)⁺ RXN-12105 Hydrogen ion + 2,5-Diketo-D-gluconate + NADPH <> 5-Keto-D-gluconate + NADP YIAE1-RXN NADP <> 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion R08878 2-Dehydro-D-gluconate + NADP <> 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion R05823 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion + NADPH > NADP + 5-Keto-D-gluconate + 5-Keto-D-gluconate PW_R005647 2,5-Diketo-D-gluconate + Hydrogen ion + NADPH + NADPH > NADP + 2-Keto-L-gluconate + 2-Dehydro-D-gluconate PW_R005648 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