Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:32:52 UTC
Update Date2024-04-30 19:38:13 UTC
Metabolite IDMMDBc0029575
Metabolite Identification
Common NameGuanosine diphosphate mannose
DescriptionGDP-mannose is a nucleoside diphosphate sugar that is important in the production of fucosylated oligosaccharides. GDP-mannose is transformed to GDP-fucose via three enzymatic reactions carried out by two proteins, GDP-mannose 4,6-dehydratase (GMD) and a second enzyme, GDP-keto-6-deoxymannose 3,5-epimerase, 4-reductase. GDP-mannose 4,6-dehydratase (EC 4.2.1.47) catalyzes the chemical reaction: GDP-mannose <--> GDP-4-dehydro-6-deoxy-D-mannose + H2O. The epimerase converts the GDP-4-dehydro-6-deoxy-D-mannose to GDP-fucose. (PMID: 12651883 ). GDP-mannose is also synthesized from mannose 1-phosphate via the enzyme ATP-mannose-1-phosphate-guanyltransferase and GTP.
Structure
Synonyms
ValueSource
GDP-D-MannoseChEBI
GDPmannoseChEBI
Guanosine 5'-(trihydrogen diphosphate), mono-alpha-D-mannopyranosyl esterChEBI
Guanosine diphosphomannoseChEBI
Guanosine pyrophosphate mannoseChEBI
GDP-alpha-D-MannoseKegg
Guanosine 5'-(trihydrogen diphosphate), mono-a-D-mannopyranosyl esterGenerator
Guanosine 5'-(trihydrogen diphosphate), mono-α-D-mannopyranosyl esterGenerator
Guanosine 5'-(trihydrogen diphosphoric acid), mono-a-D-mannopyranosyl esterGenerator
Guanosine 5'-(trihydrogen diphosphoric acid), mono-alpha-D-mannopyranosyl esterGenerator
Guanosine 5'-(trihydrogen diphosphoric acid), mono-α-D-mannopyranosyl esterGenerator
Guanosine pyrophosphoric acid mannoseGenerator
GDP-a-D-MannoseGenerator
GDP-Α-D-mannoseGenerator
Guanosine diphosphoric acid mannoseGenerator
GDP MannoseHMDB
GDP-GlucoseHMDB
GDP-MannoseHMDB
Pyrophosphate mannose, guanosineHMDB
Diphosphomannose, guanosineHMDB
Mannose, guanosine diphosphateHMDB
Diphosphate mannose, guanosineHMDB
Mannose, guanosine pyrophosphateHMDB
Mannose, GDPHMDB
Guanosine 5'-(trihydrogen diphosphate) p'-mannosyl esterHMDB
Guanosine 5'-(trihydrogen pyrophosphate) mono-D-mannosyl esterHMDB
Guanosine 5'-(trihydrogen pyrophosphate) monomannopyranosyl esterHMDB
Guanosine 5'-(trihydrogen pyrophosphate) monomannosyl esterHMDB
Guanosine 5'-diphosphate D-mannoseHMDB
Guanosine 5'-pyrophosphate D-mannosyl esterHMDB
Guanosine 5'-pyrophosphate alpha-D-mannosyl esterHMDB
Guanosine 5'-pyrophosphate α-D-mannosyl esterHMDB
Guanosine 5’-(trihydrogen diphosphate) p’-mannosyl esterHMDB
Guanosine 5’-(trihydrogen pyrophosphate) mono-D-mannosyl esterHMDB
Guanosine 5’-(trihydrogen pyrophosphate) monomannopyranosyl esterHMDB
Guanosine 5’-(trihydrogen pyrophosphate) monomannosyl esterHMDB
Guanosine 5’-diphosphate D-mannoseHMDB
Guanosine 5’-pyrophosphate D-mannosyl esterHMDB
Guanosine 5’-pyrophosphate α-D-mannosyl esterHMDB
Guanosine diphosphate mannoseHMDB
Molecular FormulaC16H25N5O16P2
Average Mass605.3411
Monoisotopic Mass605.077152801
IUPAC Name[({[(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
Traditional Nameguanosine diphosphomannose
CAS Registry Number3123-67-9
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
InChI Identifier
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
InChI KeyMVMSCBBUIHUTGJ-GDJBGNAASA-N