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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-03-23 06:07:48 UTC
Update Date2018-05-17 01:57:39 UTC
HMDB IDHMDB0062759
Secondary Accession Numbers
  • HMDB62759
Metabolite Identification
Common NameGDP-alpha-D-mannose(2-)
DescriptionGuanosine diphosphate mannose, also known as gdpmannose or pyrophosphate mannose, guanosine, 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 slightly soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, guanosine diphosphate mannose is primarily located in the cytoplasm and mitochondria. Guanosine diphosphate mannose exists in all eukaryotes, ranging from yeast to humans. Guanosine diphosphate mannose participates in a number of enzymatic reactions. In particular, Guanosine diphosphate mannose can be biosynthesized from D-mannose 1-phosphate through the action of the enzyme mannose-1-phosphate guanyltransferase beta. In addition, Guanosine diphosphate mannose can be converted into GDP-4-dehydro-6-deoxy-D-mannose through the action of the enzyme GDP-mannose 4,6 dehydratase. In humans, guanosine diphosphate mannose is involved in the fructose and mannose degradation pathway and the fructose intolerance, hereditary pathway. Guanosine diphosphate mannose is also involved in the metabolic disorder called the fructosuria pathway. Outside of the human body, guanosine diphosphate mannose can be found in a number of food items such as garden rhubarb, rambutan, vanilla, and jew's ear. This makes guanosine diphosphate mannose a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
GDP-D-MannoseChEBI
GDPmannoseChEBI
Guanosine 5'-(trihydrogen diphosphate), mono-alpha-D-mannopyranosyl esterChEBI
Guanosine diphosphomannoseChEBI
Guanosine pyrophosphate mannoseChEBI
Guanosine diphosphoric acid mannoseGenerator
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 MannoseHMDB
GDP-GlucoseHMDB
GDP-MannoseHMDB
Pyrophosphate mannose, guanosineMeSH
Diphosphomannose, guanosineMeSH
Mannose, guanosine diphosphateMeSH
Diphosphate mannose, guanosineMeSH
Mannose, guanosine pyrophosphateMeSH
Mannose, GDPMeSH
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({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid
Traditional Nameguanosine diphosphomannose
CAS Registry NumberNot Available
SMILES
OCC1OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C2NC(=N)N=C3O)C(O)C(O)C1O
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)
InChI KeyMVMSCBBUIHUTGJ-UHFFFAOYSA-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
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Primary alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.71 g/lALOGPS
LogP-1.43ALOGPS
Predicted Properties
PropertyValueSource
logP-1.8ALOGPS
logP-5.5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.31ChemAxon
pKa (Strongest Basic)3.19ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area327.43 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity118.51 m³·mol⁻¹ChemAxon
Polarizability48.77 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bu-5842490000-d73f755e03b8ad234b29View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01r6-7882509000-02adbc06a0f79e803d88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0910510000-30a5518df6f0f53ad7b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0910000000-48aef418f3aa94cc35f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-438261daf883fac47d6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1901325000-e5d0bcd5db4a59b606f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1901100000-a8c00836fd0ca5a71ad1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdl-3900000000-358726d071759c859d9eView in MoNA
Biological Properties
Cellular LocationsNot Available
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
FoodDB IDFDB012326
KNApSAcK IDC00007246
Chemspider ID17372
KEGG Compound IDC00096
BioCyc IDGDP-MANNOSE
BiGG ID1460457
Wikipedia LinkGuanosine diphosphate mannose
METLIN ID6045
PubChem Compound18396
PDB IDGDD
ChEBI ID15820
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available