Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 20:13:10 UTC
Update Date2025-10-07 16:09:30 UTC
Metabolite IDMMDBc0056010
Metabolite Identification
Common NameGDP-D-glucose
DescriptionGDP-D-glucose is a nucleotide sugar belonging to the class of nucleoside diphosphate sugars. Its chemical structure consists of a guanosine diphosphate moiety linked to a D-glucose molecule, which is critical for various biosynthetic pathways. In organisms like Caenorhabditis elegans and mammals, GDP-D-glucose is involved in the regulation of nucleotide sugar pools, with GDP-D-glucose phosphorylase catalyzing its phosphorolysis to GDP and D-glucose 1-phosphate (PMID:21507950 ). This enzyme is predominantly expressed in the nervous and male reproductive systems, indicating its potential roles in these tissues (PMID:21507950 ). Additionally, GDP-D-glucose accumulation in mutant strains lacking GDP-D-glucose phosphorylase suggests its role in maintaining metabolic balance, particularly in relation to GDP-D-mannose pyrophosphorylase activity (PMID:21507950 ). Furthermore, GDP-D-glucose is implicated in the extended VTC2 cycle, linking photosynthesis to vitamin C biosynthesis and cell-wall metabolism in plants (PMID:17950389 ). Its competitive inhibition of certain enzymes highlights its significance in metabolic regulation (PMID:12954627 ). Overall, GDP-D-glucose serves as a crucial metabolite in various biochemical pathways, reflecting its importance in both plant and animal systems.
Structure
Synonyms
ValueSource
GDP-D-GlucoseChEBI
GDP-D-Glucose dianionChEBI
Molecular FormulaC16H23N5O16P2
Average Mass603.328
Monoisotopic Mass603.062600836
IUPAC Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-({[hydroxy({[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl phosphono]oxy}methyl)oxolan-2-yl]-2-imino-3,9-dihydro-2H-purin-6-olate
Traditional Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-({[hydroxy([(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphoryl phosphono]oxy}methyl)oxolan-2-yl]-2-imino-3H-purin-6-olate
CAS Registry NumberNot Available
SMILES
[H][C@]1(COP([O-])(=O)OP(O)(=O)OC2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3[O-])[C@]([H])(O)[C@]1([H])O
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)/p-2/t4-,5-,7-,8-,9+,10-,11-,14-,15?/m1/s1
InChI KeyMVMSCBBUIHUTGJ-ZQVROCHNSA-L