2.0 2012-07-30 14:55:18 -0600 2015-06-03 17:21:10 -0600 ECMDB21327 M2MDB001729 dTDP-4-Dehydro-6-deoxy-L-mannose 4,6-Dideoxy-4-oxo-dTDP-D-glucose is a product of the enzyme TDP-glucose 4,6-dehydratase [EC:4.2.1.46] in the Nucleotide sugars metabolism (KEGG) 4,6-Dideoxy-4-oxo-dTDP-D-glucose DTDP-4-Dehydro-6-deoxy-D-glucose DTDP-4-Dehydro-6-deoxy-L-mannose DTDP-4-Dehydro-L-rhamnose DTDP-4-Oxo-6-deoxy-D-glucose DTDP-4-Oxo-6-deoxy-L-mannose DTDP-4-Oxo-L-rhamnose DTDP-DDMan TDP-4-Keto-6-deoxy-D-glucose TDP-4-Oxo-6-deoxy-D-glucose Thymidine 5'-[3-(6-deoxy-L-lyxo-hexopyranosyl-4-ulose) dihydrogen diphosphate] Thymidine 5'-[3-(6-deoxy-L-lyxo-hexopyranosyl-4-ulose) dihydrogen diphosphoric acid] C16H24N2O15P2 546.3137 546.065191132 [({[(3R,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid {[(3R,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy(hydroxy)phosphoryl}oxy[(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxyphosphinic acid [H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(=O)OP(O)(=O)OC1([H])O[C@@]([H])(C)C(=O)[C@@]([H])(O)[C@@]1([H])O)N1C=C(C)C(O)=NC1=O InChI=1S/C16H24N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-10,12-13,15,19,21-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8-,9+,10+,12+,13+,15?/m0/s1 PSXWNITXWWECNY-WPTIAVDBSA-N Solid Cytosol logp -1.11 ALOGPS logs -1.52 ALOGPS solubility 1.65e+01 g/l ALOGPS logp -1.7 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac [({[(3R,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid ChemAxon average_mass 546.3137 ChemAxon mono_mass 546.065191132 ChemAxon smiles [H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(=O)OP(O)(=O)OC1([H])O[C@@]([H])(C)C(=O)[C@@]([H])(O)[C@@]1([H])O)N1C=C(C)C(O)=NC1=O ChemAxon formula C16H24N2O15P2 ChemAxon inchi InChI=1S/C16H24N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-10,12-13,15,19,21-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8-,9+,10+,12+,13+,15?/m0/s1 ChemAxon inchikey PSXWNITXWWECNY-WPTIAVDBSA-N ChemAxon polar_surface_area 251.41 ChemAxon refractivity 107.31 ChemAxon polarizability 45.3 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 13 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Streptomycin biosynthesis ec00521 Polyketide sugar unit biosynthesis ec00523 Metabolic pathways eco01100 Specdb::CMs 1083963 Specdb::EiMs 3902 Specdb::NmrOneD 265548 Specdb::NmrOneD 265549 Specdb::NmrOneD 265550 Specdb::NmrOneD 265551 Specdb::NmrOneD 265552 Specdb::NmrOneD 265553 Specdb::NmrOneD 265554 Specdb::NmrOneD 265555 Specdb::NmrOneD 265556 Specdb::NmrOneD 265557 Specdb::NmrOneD 265558 Specdb::NmrOneD 265559 Specdb::NmrOneD 265560 Specdb::NmrOneD 265561 Specdb::NmrOneD 265562 Specdb::NmrOneD 265563 Specdb::NmrOneD 265564 Specdb::NmrOneD 265565 Specdb::NmrOneD 265566 Specdb::NmrOneD 265567 Specdb::MsMs 29330 Specdb::MsMs 29331 Specdb::MsMs 29332 Specdb::MsMs 35888 Specdb::MsMs 35889 Specdb::MsMs 35890 HMDB01399 685 391477 C00688 15744 van 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. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 dTDP-4-dehydrorhamnose 3,5-epimerase P37745 RMLC_ECOLI rfbC http://ecmdb.ca/proteins/P37745.xml dTDP-4-dehydrorhamnose reductase P37760 RMLD_ECOLI rfbD http://ecmdb.ca/proteins/P37760.xml 4,6-Dideoxy-4-oxo-dTDP-D-glucose <> dTDP-4-Dehydro-6-deoxy-L-mannose R06514 dTDP-4-Dehydro-6-deoxy-L-mannose + Hydrogen ion + NADPH <> Deoxythymidine diphosphate-L-rhamnose + NADP R02777 Deoxythymidine diphosphate-L-rhamnose + NADP <> dTDP-4-Dehydro-6-deoxy-L-mannose + NADPH + Hydrogen ion R02777 dTDP-4-dehydro-6-deoxy-D-glucose > dTDP-4-Dehydro-6-deoxy-L-mannose dTDP-6-deoxy-L-mannose + NADP > dTDP-4-Dehydro-6-deoxy-L-mannose + NADPH dTDP-4-Dehydro-6-deoxy-L-mannose + Hydrogen ion + NADPH <> Deoxythymidine diphosphate-L-rhamnose + NADP 4 4,6-Dideoxy-4-oxo-dTDP-D-glucose <> dTDP-4-Dehydro-6-deoxy-L-mannose dTDP-4-Dehydro-6-deoxy-L-mannose + Hydrogen ion + NADPH <> Deoxythymidine diphosphate-L-rhamnose + NADP 4 4,6-Dideoxy-4-oxo-dTDP-D-glucose <> dTDP-4-Dehydro-6-deoxy-L-mannose