2.02012-05-31 14:20:36 -06002015-09-17 15:41:46 -0600ECMDB11731M2MDB0008205-Keto-D-gluconate5-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-gluconate5-Dehydro-D-gluconic acid5-Dehydrogluconate5-Dehydrogluconic acid5-k-Gluconate5-k-Gluconic acid5-Keto-D-gluconate5-Keto-D-gluconic acid5-Ketogluconate5-Ketogluconic acid5K-Gluconate5K-Gluconic acidD-tagaturonateD-tagaturonic acidHex-5-ulosonateHex-5-ulosonic acidTagaturonateTagaturonic acidC6H10O7194.1394194.042652674(2R,3S,4S)-2,3,4,6-tetrahydroxy-5-oxohexanoic acid5-dehydrogluconate3470-36-8OCC(=O)C(O)C(O)C(O)C(O)=OInChI=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-NSolidCytosolExtra-organismPeriplasmCytosollogp-2.51logs-0.24solubility1.12e+02 g/llogp-2.9pka_strongest_acidic3.24pka_strongest_basic-3.3iupac(2R,3S,4S)-2,3,4,6-tetrahydroxy-5-oxohexanoic acidaverage_mass194.1394mono_mass194.042652674smilesOCC(=O)C(O)C(O)C(O)C(O)=OformulaC6H10O7inchiInChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h3-5,7,9-11H,1H2,(H,12,13)inchikeyIZSRJDGCGRAUAR-UHFFFAOYSA-Npolar_surface_area135.29refractivity37.43polarizability16.32rotatable_bond_count5acceptor_count7donor_count5physiological_charge-1formal_charge0Pentose and glucuronate interconversionsec00040ketogluconate metabolismPW002003Metabolicketogluconate metabolismKETOGLUCONMET-PWYL-idonate degradationIDNCAT-PWYSpecdb::MsMs25880Specdb::MsMs25881Specdb::MsMs25882Specdb::MsMs32438Specdb::MsMs32439Specdb::MsMs32440HMDB11731157152C010625-DEHYDROGLUCONATEKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Altronate oxidoreductaseP0A6L7UXAB_ECOLIuxaBhttp://ecmdb.ca/proteins/P0A6L7.xmlUronate isomeraseP0A8G3UXAC_ECOLIuxaChttp://ecmdb.ca/proteins/P0A8G3.xmlGluconate 5-dehydrogenaseP0A9P9IDNO_ECOLIidnOhttp://ecmdb.ca/proteins/P0A9P9.xmlGlyoxylate/hydroxypyruvate reductase BP37666GHRB_ECOLIghrBhttp://ecmdb.ca/proteins/P37666.xmlL-idonate 5-dehydrogenaseP39346IDND_ECOLIidnDhttp://ecmdb.ca/proteins/P39346.xmlPutative L-galactonate oxidoreductaseP39400YJJN_ECOLIyjjNhttp://ecmdb.ca/proteins/P39400.xmlGnt-II system L-idonate transporterP39344IDNT_ECOLIidnThttp://ecmdb.ca/proteins/P39344.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlD-Altronate + NAD <> Hydrogen ion + NADH + 5-Keto-D-gluconate + D-TagaturonateR02555D-Galacturonate <> 5-Keto-D-gluconateR019832,5-Diketo-D-gluconate + Hydrogen ion + NADH > 5-Keto-D-gluconate + NAD2,5-Diketo-D-gluconate + Hydrogen ion + NADPH > 5-Keto-D-gluconate + NADPYIAE1-RXN5-Keto-D-gluconate + Hydrogen ion + NADPH <> Gluconic acid + NADP5-Keto-D-gluconate + Hydrogen ion + NADH <> D-Galactonate + NAD5-Keto-D-gluconate + Hydrogen ion + NADPH > D-Galactonate + NADPD-Galactonate + NAD > Hydrogen ion + NADH + 5-Keto-D-gluconateD-Altronate + NAD <> 5-Keto-D-gluconate + NADH + Hydrogen ionR02555NAD(P)<sup>+</sup> + L-Idonate <> NAD(P)H + 5-Keto-D-gluconate + Hydrogen ion1.1.1.264-RXNNAD(P)<sup>+</sup> + Gluconic acid <> NAD(P)H + 5-Keto-D-gluconate + Hydrogen ionGLUCONATE-5-DEHYDROGENASE-RXNHydrogen ion + 2,5-Diketo-D-gluconate + NADPH <> 5-Keto-D-gluconate + NADPYIAE1-RXNL-Idonate + NAD(P)(+) > 5-Keto-D-gluconate + NAD(P)HGluconic acid + NAD(P)(+) > 5-Keto-D-gluconate + NAD(P)HGluconic acid + NAD + NADP <> 5-Keto-D-gluconate + NADH + NADPH + Hydrogen ionR01738 R01740 L-Idonate + NAD + NADP <> 5-Keto-D-gluconate + NADH + NADPH + Hydrogen ionR05683 R05684 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion + NADPH > NADP + 5-Keto-D-gluconate + 5-Keto-D-gluconatePW_R005647L-Idonate + NADP > Hydrogen ion + NADPH + 5-Keto-D-gluconate + NADPH + 5-Keto-D-gluconatePW_R0056525-Keto-D-gluconate + Hydrogen ion + NADPH + 5-Keto-D-gluconate + NADPH > NADP + Gluconic acidPW_R005687