2.0 2012-07-30 14:54:59 -0600 2015-06-03 17:20:55 -0600 ECMDB21219 M2MDB001627 GDP-4-Oxo-L-fucose GDP-4-oxo-L-fucose is a member of the chemical class known as Purine Nucleotide Sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. GDP-4-Oxo-L-fucose Guanosine 5'-[3-(6-deoxy-L-xylo-hexopyranosyl-4-ulose) dihydrogen diphosphate] Guanosine 5'-[3-(6-deoxy-L-xylo-hexopyranosyl-4-ulose) dihydrogen diphosphoric acid] C16H21N5O15P2 585.31 585.050938051 [(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3S,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl phosphonato]oxy}phosphonate [(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(3S,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl phosphonato]oxyphosphonate [H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP([O-])(=O)OP([O-])(=O)OC2([H])O[C@]([H])(C(=O)[C@@]([H])(O[H])[C@]2([H])O[H])C([H])([H])[H])[C@@]1([H])O[H])N1C([H])=NC2=C1N([H])C(=NC2=O)N([H])[H] InChI=1S/C16H23N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/p-2/t4-,5+,8+,9+,10+,11-,14+,15?/m0/s1 PNHLMHWWFOPQLK-WAMCPPDZSA-L Cytosol logp -0.95 ALOGPS logs -1.96 ALOGPS solubility 6.83e+00 g/l ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 2.54 ChemAxon pka_strongest_basic 1.68 ChemAxon iupac [(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3S,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl phosphonato]oxy}phosphonate ChemAxon average_mass 585.31 ChemAxon mono_mass 585.050938051 ChemAxon smiles [H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP([O-])(=O)OP([O-])(=O)OC2([H])O[C@]([H])(C(=O)[C@@]([H])(O[H])[C@]2([H])O[H])C([H])([H])[H])[C@@]1([H])O[H])N1C([H])=NC2=C1N([H])C(=NC2=O)N([H])[H] ChemAxon formula C16H21N5O15P2 ChemAxon inchi InChI=1S/C16H23N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/p-2/t4-,5+,8+,9+,10+,11-,14+,15?/m0/s1 ChemAxon inchikey PNHLMHWWFOPQLK-WAMCPPDZSA-L ChemAxon polar_surface_area 309.7 ChemAxon refractivity 113.52 ChemAxon polarizability 48.39 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 16 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge -2 ChemAxon Specdb::NmrOneD 334858 Specdb::NmrOneD 334859 Specdb::NmrOneD 334860 Specdb::NmrOneD 334861 Specdb::NmrOneD 334862 Specdb::NmrOneD 334863 Specdb::NmrOneD 334864 Specdb::NmrOneD 334865 Specdb::NmrOneD 334866 Specdb::NmrOneD 334867 Specdb::NmrOneD 334868 Specdb::NmrOneD 334869 Specdb::NmrOneD 334870 Specdb::NmrOneD 334871 Specdb::NmrOneD 334872 Specdb::NmrOneD 334873 Specdb::NmrOneD 334874 Specdb::NmrOneD 334875 Specdb::NmrOneD 334876 Specdb::NmrOneD 334877 Specdb::MsMs 26192 Specdb::MsMs 26193 Specdb::MsMs 26194 Specdb::MsMs 32750 Specdb::MsMs 32751 Specdb::MsMs 32752 46173240 C05389 28530 CPD0-2128 GDP-L-fucose synthase P32055 FCL_ECOLI fcl http://ecmdb.ca/proteins/P32055.xml GDP-4-Dehydro-6-deoxy-D-mannose > GDP-4-Oxo-L-fucose GDP-4-Oxo-L-fucose + Hydrogen ion + NADPH > GDP-L-Fucose + NADP