2.0 2015-09-08 17:50:17 -0600 2015-09-14 16:46:40 -0600 ECMDB24228 M2MDB006345 aldehydo-D-glucuronate Aldehydo-D-glucuronate is an intermediate in beta-D-glucuronide and D-glucuronate degradation pathway in E.coli. It is a substrate for the enzyme D-glucuronate isomerase which catalyzes the reaction aldehydo-D-glucuronate -> D-fructuronate. It is also a product in the spontaneous reaction D-glucopyranuronate -> aldehydo-D-glucuronate (BioCyc compound: CPD-15530). aldehydo-D-Glucuronic acid C6H10O7 194.1394 194.042652674 (2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid aldehydo-D-glucuronic acid [H][C@](O)(C=O)[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)C(O)=O InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)/t2-,3+,4-,5-/m0/s1 IAJILQKETJEXLJ-QTBDOELSSA-N logp -2.32 ALOGPS logs -0.29 ALOGPS solubility 1.00e+02 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 3.24 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid ChemAxon average_mass 194.1394 ChemAxon mono_mass 194.042652674 ChemAxon smiles [H][C@](O)(C=O)[C@@]([H])(O)[C@]([H])(O)[C@]([H])(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/h1-5,8-11H,(H,12,13)/t2-,3+,4-,5-/m0/s1 ChemAxon inchikey IAJILQKETJEXLJ-QTBDOELSSA-N ChemAxon polar_surface_area 135.29 ChemAxon refractivity 37.21 ChemAxon polarizability 16.13 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon hexuronide and hexuronate degradation E. coli can use β-D-glucuronosides, D-glucuronate and D-fructuronate as an only sources of carbon for growth. β-D-glucuronosides are detoxification products that are excreted into the mammalian gut in the bile. They enter E.coli through an outer membrane protein called gusC. Once in the periplasmic space it is transported through a hydrogen symporter into the cytoplasm. Once inside the cytoplasm, the initial step in the degradation of β-glucuronides is hydrolysis by β-D-glucuronidase to yield D-glucuronate. This is then isomerized to D-fructuronate by D-glucuronate isomerase. D-fructuronate then undergoes an NADH-dependent reduction to D-mannonate by D-mannonate oxidoreductase. D-mannonate dehydratase subsequently catalyzes dehydration to yield 2-dehydro-3-deoxy-D-gluconate. At this point, a common enzyme, 2-keto-3-deoxygluconokinase, phosphorylates 2-dehydro-3-deoxy-D-gluconate to yield 2-dehydro-3-deoxy-D-gluconate-6-phosphate.This product is then process by KHG/KDPG aldolase which in turn produces D-Glyceraldehyde 3-phosphate and Pyruvic Acid which then go into their respective sub pathways: glycolysis and pyruvate dehydrogenase The pathway can also start from 3 other points: a hydrogen ion symporter (gluconate/fructuronate transporter GntP) of D-fructuronate, a hydrogen ion symporter (Hexuronate transporter) of aldehydo-D-galacturonate that spontaneously turns into D-tagaturonate and then undergoes an NADH-dependent reduction to D-altronate through an altronate oxidoreductase. D-altronate undergoes dehydration to yield 2-dehydro-3-deoxy-D-gluconate, the third and last point where the reaction can start from a hydrogen symporter of a 2-dehydro-3-deoy-D-gluconate. PW000834 Metabolic Specdb::CMs 1653 Specdb::CMs 1685 Specdb::MsMs 29105 Specdb::MsMs 29106 Specdb::MsMs 29107 Specdb::MsMs 35663 Specdb::MsMs 35664 Specdb::MsMs 35665 Uronate isomerase P0A8G3 UXAC_ECOLI uxaC http://ecmdb.ca/proteins/P0A8G3.xml aldehydo-D-glucuronate > D-Fructuronate PW_R003058