1.0 2016-09-30 22:41:50 UTC 2020-05-21 16:26:57 UTC BMDB0001163 BMDB01163 Guanosine diphosphate mannose Guanosine diphosphate mannose, also known as guanosine diphosphate mannose or guanosine diphosphate mannose, 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. Guanosine diphosphate mannose is possibly soluble (in water) and a strong basic compound (based on its pKa). Guanosine diphosphate mannose exists in all living species, ranging from bacteria to humans. Guanosine diphosphate mannose participates in a number of enzymatic reactions, within cattle. In particular, Guanosine diphosphate mannose can be biosynthesized from D-mannose 1-phosphate; which is catalyzed by the enzyme mannose-1-phosphate guanyltransferase beta. In addition, Guanosine diphosphate mannose can be converted into GDP-4-dehydro-6-deoxy-D-mannose; which is mediated by the enzyme GDP-mannose 4,6 dehydratase. In cattle, guanosine diphosphate mannose is involved in the metabolic pathway called the fructose and mannose degradation pathway. GDP-D-Mannose GDPmannose Guanosine 5'-(trihydrogen diphosphate), mono-alpha-D-mannopyranosyl ester Guanosine diphosphomannose Guanosine pyrophosphate mannose GDP-alpha-D-Mannose Guanosine 5'-(trihydrogen diphosphate), mono-a-D-mannopyranosyl ester Guanosine 5'-(trihydrogen diphosphate), mono-α-D-mannopyranosyl ester Guanosine 5'-(trihydrogen diphosphoric acid), mono-a-D-mannopyranosyl ester Guanosine 5'-(trihydrogen diphosphoric acid), mono-alpha-D-mannopyranosyl ester Guanosine 5'-(trihydrogen diphosphoric acid), mono-α-D-mannopyranosyl ester Guanosine pyrophosphoric acid mannose GDP-a-D-Mannose GDP-Α-D-mannose Guanosine diphosphoric acid mannose GDP Mannose GDP-Glucose GDP-Mannose Pyrophosphate mannose, guanosine Diphosphomannose, guanosine Mannose, guanosine diphosphate Diphosphate mannose, guanosine Mannose, guanosine pyrophosphate Mannose, GDP Guanosine 5'-(trihydrogen diphosphate) p'-mannosyl ester Guanosine 5'-(trihydrogen pyrophosphate) mono-D-mannosyl ester Guanosine 5'-(trihydrogen pyrophosphate) monomannopyranosyl ester Guanosine 5'-(trihydrogen pyrophosphate) monomannosyl ester Guanosine 5'-diphosphate D-mannose Guanosine 5'-pyrophosphate D-mannosyl ester Guanosine 5'-pyrophosphate alpha-D-mannosyl ester Guanosine 5'-pyrophosphate α-D-mannosyl ester Guanosine 5’-(trihydrogen diphosphate) p’-mannosyl ester Guanosine 5’-(trihydrogen pyrophosphate) mono-D-mannosyl ester Guanosine 5’-(trihydrogen pyrophosphate) monomannopyranosyl ester Guanosine 5’-(trihydrogen pyrophosphate) monomannosyl ester Guanosine 5’-diphosphate D-mannose Guanosine 5’-pyrophosphate D-mannosyl ester Guanosine 5’-pyrophosphate α-D-mannosyl ester Guanosine diphosphate mannose C16H25N5O16P2 605.3411 605.077152801 [({[(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,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid guanosine diphosphomannose 3123-67-9 NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C(=O)N1 InChI=1S/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1 MVMSCBBUIHUTGJ-GDJBGNAASA-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 Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hydroxypyrimidines Monoalkyl phosphates Monosaccharide phosphates N-substituted imidazoles Organic oxides Organic pyrophosphates Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Pentose phosphates Polyols Primary alcohols Purine ribonucleoside diphosphates Purine ribonucleoside monophosphates Purines and purine derivatives Secondary alcohols Tetrahydrofurans Alcohol Alkyl phosphate Aromatic heteropolycyclic compound Azacycle Azole Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydroxypyrimidine Imidazole Imidazopyrimidine 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 Polyol Primary alcohol Purine Purine nucleotide sugar Purine ribonucleoside diphosphate Purine ribonucleoside monophosphate Pyrimidine Secondary alcohol Tetrahydrofuran Aromatic heteropolycyclic compounds GDP-D-mannose Solid logp -1.76 ALOGPS logs -1.89 ALOGPS logp -5.3 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3.6 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,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid ChemAxon average_mass 605.3411 ChemAxon mono_mass 605.077152801 ChemAxon smiles NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C(=O)N1 ChemAxon formula C16H25N5O16P2 ChemAxon inchi InChI=1S/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1 ChemAxon inchikey MVMSCBBUIHUTGJ-GDJBGNAASA-N ChemAxon polar_surface_area 327.43 ChemAxon refractivity 118.51 ChemAxon polarizability 48.72 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 16 ChemAxon donor_count 10 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 23411 Specdb::MsMs 23412 Specdb::MsMs 23413 Specdb::MsMs 30209 Specdb::MsMs 30210 Specdb::MsMs 30211 Specdb::MsMs 1470784 Specdb::MsMs 1471120 Specdb::MsMs 2226603 Specdb::MsMs 2228143 Specdb::MsMs 2228918 Specdb::MsMs 2230503 Specdb::MsMs 2231263 Specdb::MsMs 2232960 Specdb::MsMs 2757834 Specdb::MsMs 2757835 Specdb::MsMs 2757836 Specdb::MsMs 2948451 Specdb::MsMs 2948452 Specdb::MsMs 2948453 Specdb::NmrOneD 21282 Specdb::NmrOneD 21283 Specdb::NmrOneD 21284 Specdb::NmrOneD 21285 Specdb::NmrOneD 21286 Specdb::NmrOneD 21287 Specdb::NmrOneD 21288 Specdb::NmrOneD 21289 Specdb::NmrOneD 21290 Specdb::NmrOneD 21291 Specdb::NmrOneD 21292 Specdb::NmrOneD 21293 Specdb::NmrOneD 21294 Specdb::NmrOneD 21295 Specdb::NmrOneD 21296 Specdb::NmrOneD 21297 Specdb::NmrOneD 21298 Specdb::NmrOneD 21299 Specdb::NmrOneD 21300 Specdb::NmrOneD 21301 Specdb::CMs 9956 Specdb::CMs 37952 Specdb::CMs 475905 Specdb::CMs 475906 Specdb::CMs 475907 Specdb::CMs 475908 Specdb::CMs 475909 Specdb::CMs 475910 Specdb::CMs 475911 Specdb::CMs 475912 Specdb::CMs 475913 Specdb::CMs 475914 Specdb::CMs 475915 Specdb::CMs 475916 Specdb::CMs 475917 Specdb::CMs 475918 Specdb::CMs 475919 Specdb::CMs 475920 Specdb::CMs 475921 Specdb::CMs 475922 Specdb::CMs 475923 Specdb::CMs 475924 Specdb::CMs 475925 Specdb::CMs 475926 Specdb::CMs 475927 FDB030881 C00096 17372 18396 15820 GDP-MANNOSE C00007246 1460457 Guanosine diphosphate mannose 6045 Huang, Gang-Liang; Liu, Xiang; Zhang, Hou-Cheng; Wang, Peng-George. A facile two-step chemo-enzymatic synthesis of GDP-mannose. Letters in Organic Chemistry (2006), 3(9), 668-669. BMDBP00437 dTDP-D-glucose 4,6-dehydratase A6QLW2 TGDS Enzyme BMDBP00806 Dolichol-phosphate mannosyltransferase subunit 1 Q1JQ93 DPM1 Enzyme BMDBP01119 Mannose-1-phosphate guanyltransferase beta Q2YDJ9 GMPPB Enzyme