2.0 2012-05-31 14:20:36 -0600 2015-09-17 15:41:46 -0600 ECMDB11731 M2MDB000820 5-Keto-D-gluconate 5-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. 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 C6H10O7 194.1394 194.042652674 (2R,3S,4S)-2,3,4,6-tetrahydroxy-5-oxohexanoic acid 5-dehydrogluconate 3470-36-8 OCC(=O)C(O)C(O)C(O)C(O)=O 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) IZSRJDGCGRAUAR-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm Cytosol logp -2.51 ALOGPS logs -0.24 ALOGPS solubility 1.12e+02 g/l ALOGPS logp -2.9 ChemAxon pka_strongest_acidic 3.24 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (2R,3S,4S)-2,3,4,6-tetrahydroxy-5-oxohexanoic acid ChemAxon average_mass 194.1394 ChemAxon mono_mass 194.042652674 ChemAxon smiles OCC(=O)C(O)C(O)C(O)C(O)=O ChemAxon formula C6H10O7 ChemAxon 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) ChemAxon inchikey IZSRJDGCGRAUAR-UHFFFAOYSA-N ChemAxon polar_surface_area 135.29 ChemAxon refractivity 37.43 ChemAxon polarizability 16.32 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Pentose and glucuronate interconversions ec00040 ketogluconate metabolism PW002003 Metabolic ketogluconate metabolism KETOGLUCONMET-PWY L-idonate degradation IDNCAT-PWY Specdb::MsMs 25880 Specdb::MsMs 25881 Specdb::MsMs 25882 Specdb::MsMs 32438 Specdb::MsMs 32439 Specdb::MsMs 32440 HMDB11731 157 152 C01062 5-DEHYDROGLUCONATE 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 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. 18331064 Altronate oxidoreductase P0A6L7 UXAB_ECOLI uxaB http://ecmdb.ca/proteins/P0A6L7.xml Uronate isomerase P0A8G3 UXAC_ECOLI uxaC http://ecmdb.ca/proteins/P0A8G3.xml Gluconate 5-dehydrogenase P0A9P9 IDNO_ECOLI idnO http://ecmdb.ca/proteins/P0A9P9.xml Glyoxylate/hydroxypyruvate reductase B P37666 GHRB_ECOLI ghrB http://ecmdb.ca/proteins/P37666.xml L-idonate 5-dehydrogenase P39346 IDND_ECOLI idnD http://ecmdb.ca/proteins/P39346.xml Putative L-galactonate oxidoreductase P39400 YJJN_ECOLI yjjN http://ecmdb.ca/proteins/P39400.xml Gnt-II system L-idonate transporter P39344 IDNT_ECOLI idnT http://ecmdb.ca/proteins/P39344.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml D-Altronate + NAD <> Hydrogen ion + NADH + 5-Keto-D-gluconate + D-Tagaturonate R02555 D-Galacturonate <> 5-Keto-D-gluconate R01983 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 5-Keto-D-gluconate + Hydrogen ion + NADPH <> Gluconic acid + NADP 5-Keto-D-gluconate + Hydrogen ion + NADH <> D-Galactonate + NAD 5-Keto-D-gluconate + Hydrogen ion + NADPH > D-Galactonate + NADP D-Galactonate + NAD > Hydrogen ion + NADH + 5-Keto-D-gluconate D-Altronate + NAD <> 5-Keto-D-gluconate + NADH + Hydrogen ion R02555 NAD(P)⁺ + L-Idonate <> NAD(P)H + 5-Keto-D-gluconate + Hydrogen ion 1.1.1.264-RXN NAD(P)⁺ + Gluconic acid <> NAD(P)H + 5-Keto-D-gluconate + Hydrogen ion GLUCONATE-5-DEHYDROGENASE-RXN Hydrogen ion + 2,5-Diketo-D-gluconate + NADPH <> 5-Keto-D-gluconate + NADP YIAE1-RXN L-Idonate + NAD(P)(+) > 5-Keto-D-gluconate + NAD(P)H Gluconic acid + NAD(P)(+) > 5-Keto-D-gluconate + NAD(P)H Gluconic acid + NAD + NADP <> 5-Keto-D-gluconate + NADH + NADPH + Hydrogen ion R01738 R01740 L-Idonate + NAD + NADP <> 5-Keto-D-gluconate + NADH + NADPH + Hydrogen ion R05683 R05684 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion + NADPH > NADP + 5-Keto-D-gluconate + 5-Keto-D-gluconate PW_R005647 L-Idonate + NADP > Hydrogen ion + NADPH + 5-Keto-D-gluconate + NADPH + 5-Keto-D-gluconate PW_R005652 5-Keto-D-gluconate + Hydrogen ion + NADPH + 5-Keto-D-gluconate + NADPH > NADP + Gluconic acid PW_R005687