GDP-α-D-mannose (PAMDB110489)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110489
Identification
Name: GDP-α-D-mannose
Description:Conjugate base of GDP-α-D-mannose arising from deprotonation of both free OH groups of the diphosphate.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • guanosine pyrophosphate mannose
  • guanosine diphosphomannose
  • guanosine diphosphate mannose
  • GDP-mannose
Chemical Formula: C16H23N5O16P2
Average Molecular Weight: 603.33
Monoisotopic Molecular Weight: 605.0771528021
InChI Key: MVMSCBBUIHUTGJ-GDJBGNAASA-L
InChI: 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
CAS number: 3123-67-9
IUPAC Name:guanosine 5'-[3-(α-D-mannopyranosyl) diphosphate]
Traditional IUPAC Name: guanosine diphosphomannose
SMILES:C(OP(=O)([O-])OP(=O)([O-])OC1(OC(C(O)C(O)C(O)1)CO))C2(C(O)C(O)C(O2)N4(C=NC3(C(=O)NC(N)=NC=34)))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent Purine 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
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Polyol
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.77 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity118.51 m3·mol-1ChemAxon
Polarizability48.77 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
References
References:
  • Becker DJ, Lowe JB: Fucose: biosynthesis and biological function in mammals. Glycobiology. 2003 Jul;13(7):41R-53R. Epub 2003 Mar 19. [12651883 ]
Synthesis Reference: Huang, Gang-Liang; Liu, Xiang; Zhang, Hou-Cheng; Wang, Peng-George. A facile two-step chemo-enzymatic synthesis of GDP-mannose. Letters in Organic Chemistry (2006), 3(9), 668-669.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CAS3123-67-9
CAS18441-12-8
ChEBI57527
HMDBHMDB01163
IAF12601460457
KEGGC00096
MetaboLightsMTBLC57527
PubChem46878389