2.02012-07-30 14:55:31 -06002015-06-04 16:52:57 -0600ECMDB21376M2MDB001772L-IdonateL-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-IdonateL-Idonic acidC6H12O7196.1553196.058302738(2R,3S,4R,5S)-2,3,4,5,6-pentahydroxyhexanoic acidL-idonic acid1114-17-6[H][C@](O)(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]([H])(O)C(O)=OInChI=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/s1RGHNJXZEOKUKBD-SKNVOMKLSA-NCytoplasmlogp-2.57logs-0.09solubility1.59e+02 g/llogp-3.4pka_strongest_acidic3.39pka_strongest_basic-3iupac(2R,3S,4R,5S)-2,3,4,5,6-pentahydroxyhexanoic acidaverage_mass196.1553mono_mass196.058302738smiles[H][C@](O)(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]([H])(O)C(O)=OformulaC6H12O7inchiInChI=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/s1inchikeyRGHNJXZEOKUKBD-SKNVOMKLSA-Npolar_surface_area138.45refractivity38.27polarizability17.02rotatable_bond_count5acceptor_count7donor_count6physiological_charge-1formal_charge0ketogluconate metabolismPW002003Metabolicketogluconate metabolismKETOGLUCONMET-PWYL-idonate degradationIDNCAT-PWYSpecdb::CMs1084427Specdb::NmrOneD343128Specdb::NmrOneD343129Specdb::NmrOneD343130Specdb::NmrOneD343131Specdb::NmrOneD343132Specdb::NmrOneD343133Specdb::NmrOneD343134Specdb::NmrOneD343135Specdb::NmrOneD343136Specdb::NmrOneD343137Specdb::NmrOneD343138Specdb::NmrOneD343139Specdb::NmrOneD343140Specdb::NmrOneD343141Specdb::NmrOneD343142Specdb::NmrOneD343143Specdb::NmrOneD343144Specdb::NmrOneD343145Specdb::NmrOneD343146Specdb::NmrOneD343147Specdb::MsMs25904Specdb::MsMs25905Specdb::MsMs25906Specdb::MsMs32462Specdb::MsMs32463Specdb::MsMs32464604584C0077017796L-IDONATEKeseler, 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-D590.21097882van 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 370:17-25.17765195Bausch, C., Ramsey, M., Conway, T. (2004). "Transcriptional organization and regulation of the L-idonic acid pathway (GntII system) in Escherichia coli." J Bacteriol 186:1388-1397.14973046Glyoxylate/hydroxypyruvate reductase BP37666GHRB_ECOLIghrBhttp://ecmdb.ca/proteins/P37666.xmlL-idonate 5-dehydrogenaseP39346IDND_ECOLIidnDhttp://ecmdb.ca/proteins/P39346.xmlGnt-II system L-idonate transporterP39344IDNT_ECOLIidnThttp://ecmdb.ca/proteins/P39344.xmlL-Idonate + NADP <> 5-Dehydro-D-gluconate + NADPH + Hydrogen ionR05684NAD(P)<sup>+</sup> + L-Idonate <> NAD(P)H + 5-Keto-D-gluconate + Hydrogen ion1.1.1.264-RXN2-keto-L-gulonate + NAD(P)H + Hydrogen ion > L-Idonate + NAD(P)<sup>+</sup>RXN-12106Hydrogen ion + 2-Dehydro-D-gluconate + NADPH <> L-Idonate + NADPYIAE2-RXNL-Idonate + NAD(P)(+) > 5-Keto-D-gluconate + NAD(P)HL-Idonate + NAD + NADP <> 5-Keto-D-gluconate + NADH + NADPH + Hydrogen ionR05683 R05684 2-Keto-L-gluconate + Hydrogen ion + NADPH + 2-Dehydro-D-gluconate + NADPH > NADP + L-IdonatePW_R005649L-Idonate + NADP > Hydrogen ion + NADPH + 5-Keto-D-gluconate + NADPH + 5-Keto-D-gluconatePW_R005652