2.0 2012-10-10 12:21:53 -0600 2015-06-03 17:26:09 -0600 ECMDB23202 M2MDB003592 UDP-beta-L-Threo-pentapyranos-4-ulose UDP-beta-L-Threo-pentapyranos-4-ulose is an intermediate in the polymixin resistance pathway. It is a substrate for the enzyme UDP-4-amino-4-deoxy-L-arabinose aminotransferase which catalyzes the reaction UDP-4-amino-4-deoxy-beta-L-arabinopyranose + 2-oxoglutarate = UDP-beta-L-threo-pentapyranos-4-ulose + L-glutamate. Some Gram-negative bacteria, specifically Salmonella typhimurium and Escherichia coli, can become resistant to polymyxin by the modification of their lipid A structure via the attachment of 4-amino-4-deoxy-L-arabinopyranose (L-Ara4N) groups to one or more phosphate groups. This addition causes an absolute increase in lipid A charge, thus lowering the affinity of positively charged polymyxins. UDP-b-L-threo-Pentapyranos-4-ulose UDP-β-L-threo-Pentapyranos-4-ulose C14H20N2O16P2 534.2599 534.028805626 {[(2R,3S,4R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}[({[(2R,3R,4R)-3,4-dihydroxy-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid [(2R,3S,4R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy({[(2R,3R,4R)-3,4-dihydroxy-5-oxooxan-2-yl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid [H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])OCC(=O)[C@]([H])(O)[C@@]2([H])O)OC([H])(N2C=CC(O)=NC2=O)[C@]([H])(O)[C@]1([H])O InChI=1S/C14H20N2O16P2/c17-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)16-2-1-7(18)15-14(16)23/h1-2,6,8-13,19-22H,3-4H2,(H,24,25)(H,26,27)(H,15,18,23)/t6-,8+,9-,10-,11-,12?,13-/m1/s1 URJZIQLTPCJVMW-SVROINDSSA-N logp -1.18 ALOGPS logs -1.41 ALOGPS solubility 2.06e+01 g/l ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac {[(2R,3S,4R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}[({[(2R,3R,4R)-3,4-dihydroxy-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid ChemAxon average_mass 534.2599 ChemAxon mono_mass 534.028805626 ChemAxon smiles [H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])OCC(=O)[C@]([H])(O)[C@@]2([H])O)OC([H])(N2C=CC(O)=NC2=O)[C@]([H])(O)[C@]1([H])O ChemAxon formula C14H20N2O16P2 ChemAxon inchi InChI=1S/C14H20N2O16P2/c17-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)16-2-1-7(18)15-14(16)23/h1-2,6,8-13,19-22H,3-4H2,(H,24,25)(H,26,27)(H,15,18,23)/t6-,8+,9-,10-,11-,12?,13-/m1/s1 ChemAxon inchikey URJZIQLTPCJVMW-SVROINDSSA-N ChemAxon polar_surface_area 271.64 ChemAxon refractivity 99.97 ChemAxon polarizability 42.87 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 14 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1083786 Specdb::NmrOneD 269418 Specdb::NmrOneD 269419 Specdb::NmrOneD 269420 Specdb::NmrOneD 269421 Specdb::NmrOneD 269422 Specdb::NmrOneD 269423 Specdb::NmrOneD 269424 Specdb::NmrOneD 269425 Specdb::NmrOneD 269426 Specdb::NmrOneD 269427 Specdb::NmrOneD 269428 Specdb::NmrOneD 269429 Specdb::NmrOneD 269430 Specdb::NmrOneD 269431 Specdb::NmrOneD 269432 Specdb::NmrOneD 269433 Specdb::NmrOneD 269434 Specdb::NmrOneD 269435 Specdb::NmrOneD 269436 Specdb::NmrOneD 269437 Specdb::MsMs 27137 Specdb::MsMs 27138 Specdb::MsMs 27139 Specdb::MsMs 33695 Specdb::MsMs 33696 Specdb::MsMs 33697 Bifunctional polymyxin resistance protein ArnA P77398 ARNA_ECOLI arnA http://ecmdb.ca/proteins/P77398.xml UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase P77690 ARNB_ECOLI arnB http://ecmdb.ca/proteins/P77690.xml UDP-Glucuronic acid + NAD > UDP-beta-L-Threo-pentapyranos-4-ulose + Carbon dioxide + NADH 4-Amino-4-deoxy-L-arabinose + Oxoglutaric acid > UDP-beta-L-Threo-pentapyranos-4-ulose + DL-Glutamic acid