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Showing Compound GDP-L-fucose (FDB021816)

Record Information
Version1.0
Creation date2011-04-11 17:01:44 UTC
Update date2019-11-26 03:20:54 UTC
Primary IDFDB021816
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGDP-L-fucose
DescriptionGDP-L-fucose is a sugar nucleotide and a readily available source of fucose. Fucose is a deoxyhexose that is found in nearly all plant and animal species. The monosaccharide plays several important metabolic roles in complex carbohydrates and in glycoproteins. Fucosylated oligosaccharides are involved in cell-cell recognition, selectin-mediated leukocyte-endothelial adhesion, and mouse embryogenesis. They form the basis of the Lewis-type blood group antigens, are involved in the formation of atherosclerosis, and mediate host-bacterial interactions. A decrease in the availability of fucose is associated with leukocyte adhesion deficiency type-II disorder, and fucosylated glycoproteins have been implicated in memory processes. Fucose is made available during the synthesis of fucosylated glycolipids, oligosaccharides, and glycoproteins via a sugar nucleotide intermediate, specifically GDP-L-fucose. GTP-L-fucose pyrophosphorylase (GFPP, E. C. 2.7.7.30) catalyzes the reversible condensation of guanosine triphosphate and beta-L-fucose-1-phosphate to form the nucleotide-sugar GDP-L-fucose. The enzyme functions primarily in the mammalian liver and kidney to salvage free L-fucose during the breakdown of glycolipids and glycoproteins. (PMID: 16086588) [HMDB]
CAS Number15839-70-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Diphosphate fucose, guanosineMeSH
Fucose, guanosine diphosphateMeSH
Fucose, GDPMeSH
Guanosine diphosphate fucoseMeSH
Guanosine diphosphofucoseMeSH
Diphosphofucose, guanosineMeSH
GDP FucoseMeSH
(6-Deoxy-beta-L-galactopyranosyl) esterHMDB
GDP-beta-L-FucoseHMDB
Guanosine diate fucoseHMDB
Guanosine diofucoseHMDB
Predicted Properties
PropertyValueSource
Water Solubility7.02 g/LALOGPS
logP-1.4ALOGPS
logP-4.7ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.71ChemAxon
pKa (Strongest Basic)3.38ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area308.19 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity127.55 m³·mol⁻¹ChemAxon
Polarizability50.36 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC16H25N5O15P2
IUPAC name[({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phosphinic acid
InChI IdentifierInChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)
InChI KeyLQEBEXMHBLQMDB-UHFFFAOYSA-N
Isomeric SMILESCC1OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C2NC(=N)N=C3O)C(O)C(O)C1O
Average Molecular Weight589.3417
Monoisotopic Molecular Weight589.082238179
Classification
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
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetrahydrofuran
  • Vinylogous amide
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Polyol
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID388350
ChEMBL IDNot Available
KEGG Compound IDC00325
Pubchem Compound ID439211
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01095
CRC / DFC (Dictionary of Food Compounds) IDFOG76-Z:FOG76-Z
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34623
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Alpha-(1,3)-fucosyltransferaseFUT9Q9Y231
Galactoside 2-alpha-L-fucosyltransferase 2FUT2Q10981
Galactoside 2-alpha-L-fucosyltransferase 1FUT1P19526
GDP-L-fucose synthaseTSTA3Q13630
Alpha-(1,6)-fucosyltransferaseFUT8Q9BYC5
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064 map00051
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference