2.0 2012-05-31 14:22:44 -0600 2015-06-03 17:19:07 -0600 ECMDB20011 M2MDB000860 (4S)-4,6-Dihydroxy-2,5-dioxohexanoate (4S)-4,6-Dihydroxy-2,5-dioxohexanoate (2,5-Diketo-3-deoxy-D-gluconate or 3-Deoxy-D-glycero-2,5-hexodiulosonate) is involved in pentose and glucuronate interconversions. It is a substrate for 2-dehydro-3-deoxy-D-gluconate 5-dehydrogenase. This enzyme catalyzes the reduction of 2,5-diketo-3-deoxygluconate (DKII or 4,6-dihydroxy-2,5-dioxohexanoate) into 2-keto-3-deoxygluconate (KDG or 2-dehydro-3-deoxygluconate) with a concomitant oxidation of NADH. It is also a substrate for 4-deoxy-L-threo-5-hexosulose-uronate ketol-isomerase. This enzyme catalyzes the isomerization of 5-dehydro-4-deoxy-D-glucuronate to 3-deoxy-D-glycero-2,5-hexodiulosonate. (4S)-4,6-dihydroxy-2,5-dioxohexanoate (4S)-4,6-dihydroxy-2,5-dioxohexanoic acid 2,5-Diketo-3-deoxy-D-gluconate 2,5-Diketo-3-deoxy-D-gluconic acid 3-Deoxy-D-glycero-2,5-hexodiulosonate 3-Deoxy-D-glycero-2,5-hexodiulosonic acid 3-Deoxy-D-glycero-hexo-2,5-diulosonate 3-Deoxy-D-glycero-hexo-2,5-diulosonic acid C6H8O6 176.1241 176.032087988 (4S)-4,6-dihydroxy-2,5-dioxohexanoic acid 2,5-diketo-3-deoxy-D-gluconate [H][C@](O)(CC(=O)C(O)=O)C(=O)CO InChI=1S/C6H8O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,7-8H,1-2H2,(H,11,12)/t3-/m0/s1 IBGYNIRCYXIAON-VKHMYHEASA-N Cytoplasm Periplasm logp -1.35 ALOGPS logs -0.42 ALOGPS solubility 6.67e+01 g/l ALOGPS logp -1.3 ChemAxon pka_strongest_acidic 2.74 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (4S)-4,6-dihydroxy-2,5-dioxohexanoic acid ChemAxon average_mass 176.1241 ChemAxon mono_mass 176.032087988 ChemAxon smiles [H][C@](O)(CC(=O)C(O)=O)C(=O)CO ChemAxon formula C6H8O6 ChemAxon inchi InChI=1S/C6H8O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,7-8H,1-2H2,(H,11,12)/t3-/m0/s1 ChemAxon inchikey IBGYNIRCYXIAON-VKHMYHEASA-N ChemAxon polar_surface_area 111.9 ChemAxon refractivity 35.47 ChemAxon polarizability 14.89 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Pentose and glucuronate interconversions ec00040 Collection of Reactions without pathways PW001891 Metabolic Specdb::CMs 1083739 Specdb::NmrOneD 250388 Specdb::NmrOneD 250389 Specdb::NmrOneD 250390 Specdb::NmrOneD 250391 Specdb::NmrOneD 250392 Specdb::NmrOneD 250393 Specdb::NmrOneD 250394 Specdb::NmrOneD 250395 Specdb::NmrOneD 250396 Specdb::NmrOneD 250397 Specdb::NmrOneD 250398 Specdb::NmrOneD 250399 Specdb::NmrOneD 250400 Specdb::NmrOneD 250401 Specdb::NmrOneD 250402 Specdb::NmrOneD 250403 Specdb::NmrOneD 250404 Specdb::NmrOneD 250405 Specdb::NmrOneD 250406 Specdb::NmrOneD 250407 Specdb::MsMs 24755 Specdb::MsMs 24756 Specdb::MsMs 24757 Specdb::MsMs 31313 Specdb::MsMs 31314 Specdb::MsMs 31315 440303 389277 C04349 15623 CPD-1945 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 2-dehydro-3-deoxy-D-gluconate 5-dehydrogenase P37769 KDUD_ECOLI kduD http://ecmdb.ca/proteins/P37769.xml 4-deoxy-L-threo-5-hexosulose-uronate ketol-isomerase Q46938 KDUI_ECOLI kduI http://ecmdb.ca/proteins/Q46938.xml 2-Keto-3-deoxy-D-gluconic acid + NAD <> (4S)-4,6-Dihydroxy-2,5-dioxohexanoate + NADH + Hydrogen ion R01542 5-Dehydro-4-deoxy-D-glucuronate <> (4S)-4,6-Dihydroxy-2,5-dioxohexanoate R04383 2-Keto-3-deoxy-D-gluconic acid + NAD > (4S)-4,6-Dihydroxy-2,5-dioxohexanoate + NADH 5-Dehydro-4-deoxy-D-glucuronate > (4S)-4,6-Dihydroxy-2,5-dioxohexanoate