1.0 2016-09-30 22:44:29 UTC 2020-05-21 16:28:32 UTC BMDB0001346 BMDB01346 GDP-4-Dehydro-6-deoxy-D-mannose GDP-4-Dehydro-6-deoxy-D-mannose, also known as GDP-4-dehydro-D-rhamnose or GDP-4-keto-6-deoxymannose, belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. GDP-4-Dehydro-6-deoxy-D-mannose is possibly soluble (in water) and a strong basic compound (based on its pKa). GDP-4-Dehydro-6-deoxy-D-mannose exists in all living organisms, ranging from bacteria to humans. GDP-4-Dehydro-6-deoxy-D-mannose participates in a number of enzymatic reactions, within cattle. In particular, GDP-4-Dehydro-6-deoxy-D-mannose can be biosynthesized from guanosine diphosphate mannose through its interaction with the enzyme GDP-mannose 4,6 dehydratase. In addition, GDP-4-Dehydro-6-deoxy-D-mannose can be biosynthesized from GDP-L-fucose; which is mediated by the enzyme GDP-L-fucose synthase. In cattle, GDP-4-dehydro-6-deoxy-D-mannose is involved in the metabolic pathway called the fructose and mannose degradation pathway. GDP-4-Dehydro-6-deoxy-D-talose GDP-4-Dehydro-D-rhamnose GDP-4-Keto-6-deoxy-D-mannose GDP-4-Keto-6-deoxymannose GDP-4-oxo-6-Deoxy-D-mannose Guanosine 5'-(trihydrogen diphosphate), p'-(6-deoxy-alpha-D-lyxo-hexopyranos-4-ulos-1-yl) ester Guanosine diphosphate-4-keto-6-deoxy-D-mannose GDP-4-Dehydro-alpha-D-rhamnose GDP-4-Dehydro-6-deoxy-alpha-D-mannose Guanosine 5'-(trihydrogen diphosphate), p'-(6-deoxy-a-D-lyxo-hexopyranos-4-ulos-1-yl) ester Guanosine 5'-(trihydrogen diphosphate), p'-(6-deoxy-α-D-lyxo-hexopyranos-4-ulos-1-yl) ester Guanosine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-a-D-lyxo-hexopyranos-4-ulos-1-yl) ester Guanosine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-alpha-D-lyxo-hexopyranos-4-ulos-1-yl) ester Guanosine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-α-D-lyxo-hexopyranos-4-ulos-1-yl) ester Guanosine diphosphoric acid-4-keto-6-deoxy-D-mannose GDP-4-Dehydro-a-D-rhamnose GDP-4-Dehydro-α-D-rhamnose GDP-4-Dehydro-6-deoxy-a-D-mannose GDP-4-Dehydro-6-deoxy-α-D-mannose GDP-4-Keto-6-D-deoxymannose GDP-4-oxo-6-Deoxymannose Guanosine 5'-diphosphate 4-keto-6-deoxy-D-mannose Guanosine 5’-diphosphate 4-keto-6-deoxy-D-mannose C16H23N5O15P2 587.3258 587.066588115 [({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy})phosphinic acid gdp-4-keto-6-deoxymannose 18186-48-6 C[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@@H](O)C1=O 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)/t4-,5-,8-,9+,10-,11+,14-,15-/m1/s1 PNHLMHWWFOPQLK-BKUUWRAGSA-N belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. Organic compounds Nucleosides, nucleotides, and analogues Purine nucleotides Purine nucleotide sugars Purine nucleotide sugars 6-oxopurines Aminopyrimidines and derivatives Azacyclic compounds Cyclic ketones Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hypoxanthines Monoalkyl phosphates Monosaccharide phosphates N-substituted imidazoles Organic oxides Organic pyrophosphates Organopnictogen compounds Oxacyclic compounds Oxanes Pentose phosphates Primary amines Purine ribonucleoside diphosphates Purine ribonucleoside monophosphates Pyrimidones Secondary alcohols Tetrahydrofurans Vinylogous amides 6-oxopurine Alcohol Alkyl phosphate Amine Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Carbonyl group Cyclic ketone Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hypoxanthine Imidazole Imidazopyrimidine Ketone Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Primary amine Purine Purine nucleotide sugar Purine ribonucleoside diphosphate Purine ribonucleoside monophosphate Pyrimidine Pyrimidone Secondary alcohol Tetrahydrofuran Vinylogous amide Aromatic heteropolycyclic compounds GDP-sugar Solid logp -1.28 ALOGPS logs -1.97 ALOGPS logp -3.6 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac [({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy})phosphinic acid ChemAxon average_mass 587.3258 ChemAxon mono_mass 587.066588115 ChemAxon smiles C[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@@H](O)C1=O ChemAxon formula C16H23N5O15P2 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)/t4-,5-,8-,9+,10-,11+,14-,15-/m1/s1 ChemAxon inchikey PNHLMHWWFOPQLK-BKUUWRAGSA-N ChemAxon polar_surface_area 304.04 ChemAxon refractivity 116.2 ChemAxon polarizability 48.01 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 15 ChemAxon donor_count 8 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Fructose and Mannose Degradation SMP0087197 Specdb::MsMs 25670 Specdb::MsMs 25671 Specdb::MsMs 25672 Specdb::MsMs 32228 Specdb::MsMs 32229 Specdb::MsMs 32230 Specdb::MsMs 2798741 Specdb::MsMs 2798742 Specdb::MsMs 2798743 Specdb::MsMs 2883308 Specdb::MsMs 2883309 Specdb::MsMs 2883310 Specdb::CMs 26579 Specdb::CMs 38034 Specdb::CMs 282800 Specdb::CMs 411272 Specdb::CMs 411273 Specdb::CMs 411274 Specdb::CMs 411275 Specdb::CMs 411276 Specdb::CMs 411277 Specdb::CMs 411278 Specdb::CMs 411279 Specdb::CMs 411280 Specdb::CMs 411281 Specdb::CMs 411282 Specdb::CMs 411283 Specdb::CMs 411284 Specdb::CMs 411285 Specdb::CMs 411286 Specdb::CMs 411287 Specdb::CMs 411288 Specdb::CMs 411289 Specdb::CMs 411290 Specdb::CMs 411291 Specdb::CMs 411292 Specdb::CMs 411293 Specdb::NmrOneD 9222 Specdb::NmrOneD 9223 Specdb::NmrOneD 9224 Specdb::NmrOneD 9225 Specdb::NmrOneD 9226 Specdb::NmrOneD 9227 Specdb::NmrOneD 9228 Specdb::NmrOneD 9229 Specdb::NmrOneD 9230 Specdb::NmrOneD 9231 Specdb::NmrOneD 9232 Specdb::NmrOneD 9233 Specdb::NmrOneD 9234 Specdb::NmrOneD 9235 Specdb::NmrOneD 9236 Specdb::NmrOneD 9237 Specdb::NmrOneD 9238 Specdb::NmrOneD 9239 Specdb::NmrOneD 9240 Specdb::NmrOneD 9241 C01222 FDB022568 388554 439446 16955 C00007244 37116 6180 GDP-4-DEHYDRO-6-DEOXY-D-MANNOSE Oths, Philip J.; Mayer, Robert M.; Floss, Heinz G. Stereochemistry and mechanism of the GDP-mannose dehydratase reaction. Carbohydrate Research (1990), 198(1), 91-100. BMDBP00437 dTDP-D-glucose 4,6-dehydratase A6QLW2 TGDS Enzyme BMDBP03185 Tissue specific transplantation antigen P35B Q2KIT8 TSTA3 Enzyme