2.0 2012-05-31 14:03:06 -0600 2015-09-17 15:41:46 -0600 ECMDB04042 M2MDB000575 2-Dehydro-D-gluconate 2-Keto-L-gluconate is a derivative of gluconic acid, which occurs naturally in fruit, honey and wine and is used as a food additive, an acidity regulator. It is also used in cleaning products where it helps cleaning up mineral deposits. It is a strong chelating agent, especially in alkaline solution. It chelates the anions of calcium, iron, aluminium, copper, and other heavy metals. E. coli contains ketogluconate reductase genes, so it is likely that pathways exist for the metabolism of ketogluconate 2-Dehydro-D-gluconate 2-Dehydro-D-gluconic acid 2-Dehydro-L-idonate 2-Dehydro-L-idonic acid 2-Keto-D-gluconate 2-Keto-D-gluconic acid 2-Keto-L-gulonate 2-Keto-L-gulonic acid 2-Ketoidonate 2-Ketoidonic acid 2-Oxogluconate 2-Oxogluconic acid L-Ketoidonate L-Ketoidonic acid L-Sorbosonate L-Sorbosonic acid Provitamin C C6H10O7 194.1394 194.042652674 (3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexanoic acid 2-ketogluconic acid 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/h2-4,7-10H,1H2,(H,12,13) VBUYCZFBVCCYFD-UHFFFAOYSA-N Solid Cytoplasm Periplasm logp -2.41 ALOGPS logs -0.28 ALOGPS solubility 1.01e+02 g/l ALOGPS melting_point 157.82 logp -2.5 ChemAxon pka_strongest_acidic 2.67 ChemAxon pka_strongest_basic -3 ChemAxon iupac (3S,4R,5R)-3,4,5,6-tetrahydroxy-2-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/h2-4,7-10H,1H2,(H,12,13) ChemAxon inchikey VBUYCZFBVCCYFD-UHFFFAOYSA-N ChemAxon polar_surface_area 135.29 ChemAxon refractivity 37.65 ChemAxon polarizability 16.29 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 ketogluconate metabolism PW002003 Metabolic ketogluconate metabolism KETOGLUCONMET-PWY Specdb::CMs 1568 Specdb::CMs 1600 Specdb::MsMs 26633 Specdb::MsMs 26634 Specdb::MsMs 26635 Specdb::MsMs 33191 Specdb::MsMs 33192 Specdb::MsMs 33193 HMDB11732 50 49 C06473 CPD-377 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 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 2,3-diketo-L-gulonate reductase P37672 DLGD_ECOLI dlgD http://ecmdb.ca/proteins/P37672.xml 2,5-diketo-D-gluconic acid reductase A Q46857 DKGA_ECOLI dkgA http://ecmdb.ca/proteins/Q46857.xml NADP + Gluconic acid <> Hydrogen ion + 2-Dehydro-D-gluconate + NADPH 1.1.1.215-RXN Hydrogen ion + NADPH + 2,5-Diketo-D-gluconate <> 2-Dehydro-D-gluconate + NADP 1.1.1.274-RXN Hydrogen ion + 2-Dehydro-D-gluconate + NADPH <> L-Idonate + NADP YIAE2-RXN 2-Dehydro-D-gluconate + NADP > 2,5-didehydro-D-gluconate + NADPH Gluconic acid + NADP > 2-Dehydro-D-gluconate + NADPH 1.1.1.215-RXN Gluconic acid + NADP <> 2-Keto-D-gluconic acid + NADPH + Hydrogen ion + 2-Dehydro-D-gluconate R01739 2-Dehydro-D-gluconate + NADP <> 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion R05823 2-Keto-L-gluconate + NADPH + Hydrogen ion + 2-Dehydro-D-gluconate + NADPH > Gluconic acid + NADP PW_R005689 2-Keto-L-gluconate + Hydrogen ion + NADPH + 2-Dehydro-D-gluconate + NADPH > NADP + L-Idonate PW_R005649 2,5-Diketo-D-gluconate + Hydrogen ion + NADPH + NADPH > NADP + 2-Keto-L-gluconate + 2-Dehydro-D-gluconate PW_R005648 2 2-Dehydro-D-gluconate + NADP <>2 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion