2.0 2012-07-30 14:55:31 -0600 2015-06-04 16:52:57 -0600 ECMDB21376 M2MDB001772 L-Idonate L-idonate is a member of the chemical class known as Sugar Acids and Derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group. L-idonate is a metabolite in D-gluconate catabolism. The catabolic sequence for l-idonate is as follows: l-idonate is transported by the l-idonate transporter, IdnT; l-idonate is oxidized to 5-keto-gluconate (5KG) by l-idonate 5-dehydrogenase, IdnD; 5KG is reduced to d-gluconate by 5-keto-D-gluconate 5-reductase, IdnO; and d-gluconate is phosphorylated by a thermosensitive gluconate kinase, IdnK, to make 6-phosphogluconate (6PG), which is further catabolized via the Entner-Doudoroff pathway. Thus, IdnD and IdnO allow for the redox-coupled interconversion of l-idonate to d-gluconate via 5KG. The l-idonate catabolic pathway overlaps d-gluconate catabolism through the common intermediates d-gluconate and 6PG. (PMID: 14973046) L-Idonate L-Idonic acid C6H12O7 196.1553 196.058302738 (2R,3S,4R,5S)-2,3,4,5,6-pentahydroxyhexanoic acid L-idonic acid 1114-17-6 [H][C@](O)(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]([H])(O)C(O)=O InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3+,4-,5+/m0/s1 RGHNJXZEOKUKBD-SKNVOMKLSA-N Cytoplasm logp -2.57 ALOGPS logs -0.09 ALOGPS solubility 1.59e+02 g/l ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 3.39 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S,4R,5S)-2,3,4,5,6-pentahydroxyhexanoic acid ChemAxon average_mass 196.1553 ChemAxon mono_mass 196.058302738 ChemAxon smiles [H][C@](O)(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]([H])(O)C(O)=O ChemAxon formula C6H12O7 ChemAxon inchi InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3+,4-,5+/m0/s1 ChemAxon inchikey RGHNJXZEOKUKBD-SKNVOMKLSA-N ChemAxon polar_surface_area 138.45 ChemAxon refractivity 38.27 ChemAxon polarizability 17.02 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon ketogluconate metabolism PW002003 Metabolic ketogluconate metabolism KETOGLUCONMET-PWY L-idonate degradation IDNCAT-PWY Specdb::CMs 1084427 Specdb::NmrOneD 343128 Specdb::NmrOneD 343129 Specdb::NmrOneD 343130 Specdb::NmrOneD 343131 Specdb::NmrOneD 343132 Specdb::NmrOneD 343133 Specdb::NmrOneD 343134 Specdb::NmrOneD 343135 Specdb::NmrOneD 343136 Specdb::NmrOneD 343137 Specdb::NmrOneD 343138 Specdb::NmrOneD 343139 Specdb::NmrOneD 343140 Specdb::NmrOneD 343141 Specdb::NmrOneD 343142 Specdb::NmrOneD 343143 Specdb::NmrOneD 343144 Specdb::NmrOneD 343145 Specdb::NmrOneD 343146 Specdb::NmrOneD 343147 Specdb::MsMs 25904 Specdb::MsMs 25905 Specdb::MsMs 25906 Specdb::MsMs 32462 Specdb::MsMs 32463 Specdb::MsMs 32464 604 584 C00770 17796 L-IDONATE 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 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 Bausch, C., Ramsey, M., Conway, T. (2004). "Transcriptional organization and regulation of the L-idonic acid pathway (GntII system) in Escherichia coli." J Bacteriol 186:1388-1397. 14973046 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 Gnt-II system L-idonate transporter P39344 IDNT_ECOLI idnT http://ecmdb.ca/proteins/P39344.xml L-Idonate + NADP <> 5-Dehydro-D-gluconate + NADPH + Hydrogen ion R05684 NAD(P)⁺ + L-Idonate <> NAD(P)H + 5-Keto-D-gluconate + Hydrogen ion 1.1.1.264-RXN 2-keto-L-gulonate + NAD(P)H + Hydrogen ion > L-Idonate + NAD(P)⁺ RXN-12106 Hydrogen ion + 2-Dehydro-D-gluconate + NADPH <> L-Idonate + NADP YIAE2-RXN L-Idonate + NAD(P)(+) > 5-Keto-D-gluconate + NAD(P)H L-Idonate + NAD + NADP <> 5-Keto-D-gluconate + NADH + NADPH + Hydrogen ion R05683 R05684 2-Keto-L-gluconate + Hydrogen ion + NADPH + 2-Dehydro-D-gluconate + NADPH > NADP + L-Idonate PW_R005649 L-Idonate + NADP > Hydrogen ion + NADPH + 5-Keto-D-gluconate + NADPH + 5-Keto-D-gluconate PW_R005652