You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-08-12 19:14:46 UTC
Update Date2016-02-11 01:06:11 UTC
HMDB IDHMDB03351
Secondary Accession NumbersNone
Metabolite Identification
Common NameGDP-glucose
DescriptionGDP-glucose is a substrate for Uridine diphosphate glucose pyrophosphatase.
Structure
Thumb
Synonyms
ValueSource
(GDP-GLC)1ChEBI
GDP-D-GlucoseChEBI
GDP-GlucoseChEBI
GDPGChEBI
Guanosine 5'-(trihydrogen diphosphate), p'-alpha-D-glucopyranosyl esterChEBI
Guanosine diphosphate glucoseChEBI
Guanosine diphosphoglucoseChEBI
GDP-a-D-GlucoseGenerator
GDP-α-D-glucoseGenerator
Guanosine 5'-(trihydrogen diphosphate), p'-a-D-glucopyranosyl esterGenerator
Guanosine 5'-(trihydrogen diphosphate), p'-α-D-glucopyranosyl esterGenerator
Guanosine 5'-(trihydrogen diphosphoric acid), p'-a-D-glucopyranosyl esterGenerator
Guanosine 5'-(trihydrogen diphosphoric acid), p'-alpha-D-glucopyranosyl esterGenerator
Guanosine 5'-(trihydrogen diphosphoric acid), p'-α-D-glucopyranosyl esterGenerator
Guanosine diphosphoric acid glucoseGenerator
GDP-alpha-delta-GlucoseHMDB
Guanosine 5-pyrophosphateHMDB
P-alpha-D-Glucopyranosyl esterHMDB
P-alpha-delta-Glucopyranosyl esterHMDB
Chemical FormulaC16H25N5O16P2
Average Molecular Weight605.3411
Monoisotopic Molecular Weight605.077152801
IUPAC Name{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid
Traditional Name[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({hydroxy[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphoryl}oxy)phosphinic acid
CAS Registry Number5750-57-2
SMILES
NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H]1O
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 KeyInChIKey=MVMSCBBUIHUTGJ-LRJDVEEWSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine nucleotide sugars
Direct ParentPurine nucleotide sugars
Alternative Parents
Substituents
  • Purine nucleotide sugar
  • Purine ribonucleoside diphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Hypoxanthine
  • 6-oxopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.96 mg/mLALOGPS
logP-1.6ALOGPS
logP-4.8ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area327.43 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity118.08 m3·mol-1ChemAxon
Polarizability50.1 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023150
KNApSAcK IDNot Available
Chemspider ID559146
KEGG Compound IDC00394
BioCyc IDGDP-D-GLUCOSE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03351
Metagene LinkHMDB03351
METLIN ID6900
PubChem Compound644106
PDB IDNot Available
ChEBI ID62254
References
Synthesis ReferenceCarlson, Don M.; Hansen, R. G. The isolation and synthesis of guanosine diphosphate glucose. Journal of Biological Chemistry (1962), 237 1260-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chandra GR, Mandava N, Warthen JD Jr: Uridine diphosphate glucose:fatty acid glucosyl transferase activity of rape (Brassica napus L.) anther tissue. Biochim Biophys Acta. 1978 Oct 12;526(2):387-97. [718943 ]
  2. Orlean PA: (1,3)-beta-D-Glucan synthase from budding and filamentous cultures of the dimorphic fungus Candida albicans. Eur J Biochem. 1982 Oct;127(2):397-403. [6216107 ]

Enzymes

General function:
Involved in hydrolase activity, acting on acid anhydrides, in phosphorus-containing anhydrides
Specific function:
Hydrolyzes UDP-glucose to glucose 1-phosphate and UMP and ADP-ribose to ribose 5-phosphate and AMP. The physiological substrate is probably UDP-glucose. Poor activity on other substrates such as ADP-glucose, CDP-glucose, GDP-glucose and GDP-mannose.
Gene Name:
NUDT14
Uniprot ID:
O95848
Molecular weight:
24118.085
General function:
Not Available
Specific function:
Specific and highly efficient GDP-D-glucose phosphorylase regulating the levels of GDP-D-glucose in cells.
Gene Name:
GDPGP1
Uniprot ID:
Q6ZNW5
Molecular weight:
42362.06
Reactions
GDP-glucose + Phosphoric acid → Glucose 1-phosphate + Guanosine diphosphatedetails