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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 19:14:46 UTC
Update Date2021-09-14 15:48:15 UTC
HMDB IDHMDB0003351
Secondary Accession Numbers
  • HMDB03351
Metabolite Identification
Common NameGDP-glucose
DescriptionGDP-glucose, also known as (GDP-GLC)1 or GDP-D-glucose, 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-glucose is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1593542168
Synonyms
ValueSource
(GDP-GLC)1ChEBI
GDP-D-glucoseChEBI
GDPGChEBI
Guanosine diphosphate glucoseChEBI
Guanosine diphosphoglucoseChEBI
Guanosine diphosphoric acid glucoseGenerator
GDP-alpha-D-glucoseHMDB
Guanosine 5-pyrophosphateHMDB
P-alpha-D-Glucopyranosyl esterHMDB
GDP GlucoseMeSH, HMDB
Guanosine diphosphate glucose, (D)-isomerMeSH, HMDB
GDP-glucoseChEBI
GDP-a-D-GlucoseGenerator, HMDB
GDP-α-D-glucoseGenerator, HMDB
Guanosine 5'-diphosphate glucoseHMDB
Guanosine 5'-diphosphate-D-glucoseHMDB
Guanosine 5’-diphosphate glucoseHMDB
Guanosine 5’-diphosphate-D-glucoseHMDB
Guanosine diphosphate D-glucoseHMDB
Guanosine 5'-(trihydrogen diphosphate), P'-a-D-glucopyranosyl esterHMDB
Guanosine 5'-(trihydrogen diphosphate), P'-alpha-D-glucopyranosyl esterHMDB
Guanosine 5'-(trihydrogen diphosphate), P'-α-D-glucopyranosyl esterHMDB
Guanosine 5'-(trihydrogen diphosphoric acid), P'-a-D-glucopyranosyl esterHMDB
Guanosine 5'-(trihydrogen diphosphoric acid), P'-alpha-D-glucopyranosyl esterHMDB
Guanosine 5'-(trihydrogen diphosphoric acid), P'-α-D-glucopyranosyl esterHMDB
Guanosine 5’-(trihydrogen diphosphate), P’-a-D-glucopyranosyl esterHMDB
Guanosine 5’-(trihydrogen diphosphate), P’-α-D-glucopyranosyl esterHMDB
Guanosine 5’-(trihydrogen diphosphoric acid), P’-a-D-glucopyranosyl esterHMDB
Guanosine 5’-(trihydrogen diphosphoric acid), P’-α-D-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-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional Namegdp-α-D-glucose
CAS Registry Number5750-57-2
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-LRJDVEEWSA-N
Chemical Taxonomy
Description 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
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Vinylogous amide
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Polyol
  • Azacycle
  • Oxacycle
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Primary alcohol
  • Primary amine
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

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 g/LALOGPS
logP-1.8ALOGPS
logP-5.3ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area327.43 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity118.51 m³·mol⁻¹ChemAxon
Polarizability48.05 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bu-5842490000-d73f755e03b8ad234b292017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01r6-4982808000-88b30cc719d45bf18e402017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-05bu-5842490000-d73f755e03b8ad234b292021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0910510000-079280e60cb5f2503d3a2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0910000000-29db1fbcd1fe8812ecd32017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-5bd106e57c79720052cc2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1901445000-b4d8fa4ec316d0d695da2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2901100000-be324e85f91ed7a7c4162017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdl-3900000000-771d4718d1ce0fb3b0a52017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000009000-3f663b5fce4f431e1e252021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-4701986000-bb5e3a66be23d7de55e62021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i0-3911810000-ee275d8a12bcf1e5065c2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900002000-37d2f661727ecc1c915a2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900001000-de8f3c7c7e6a620f0e902021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-2930000000-7a0fc600f843201b86c42021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023150
KNApSAcK IDNot Available
Chemspider ID559146
KEGG Compound IDC00394
BioCyc IDGDP-D-GLUCOSE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6900
PubChem Compound644106
PDB IDNot Available
ChEBI ID62254
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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. [PubMed: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. [PubMed: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 + Phosphate → Glucose 1-phosphate + Guanosine diphosphatedetails