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Showing Compound GDP-β-L-fucose (FDB030882)

Record Information
Version1.0
Creation date2015-05-07 20:23:46 UTC
Update date2025-11-19 03:02:20 UTC
Primary IDFDB030882
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGDP-β-L-fucose
DescriptionGDP-L-fucose, also known as GDP fucose or GDP-beta-L-fucose, 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-L-fucose is a moderately basic compound (based on its pKa). GDP-L-fucose exists in all living organisms, ranging from bacteria to humans. Within humans, GDP-L-fucose participates in a number of enzymatic reactions. In particular, GDP-L-fucose can be converted into GDP-4-dehydro-6-deoxy-D-mannose through its interaction with the enzyme GDP-L-fucose synthase. In addition, GDP-L-fucose can be biosynthesized from fucose 1-phosphate through its interaction with the enzyme fucose-1-phosphate guanylyltransferase. In humans, GDP-L-fucose is involved in fructose intolerance, hereditary. Outside of the human body, GDP-L-fucose has been detected, but not quantified in, several different foods, such as wheats, rocket salad (ssp.), sacred lotus, macadamia nuts, and winter savories. This could make GDP-L-fucose a potential biomarker for the consumption of these foods.
CAS Number15839-70-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(6-Deoxy-beta-L-galactopyranosyl) esterHMDB
GDP FucoseHMDB
GDP-beta-L-FucoseHMDB
Guanosine diphosphate fucoseHMDB
Guanosine diphosphofucoseHMDB
Diphosphate fucose, guanosineHMDB
Diphosphofucose, guanosineHMDB
Fucose, GDPHMDB
Fucose, guanosine diphosphateHMDB
GDP-FucoseHMDB
GDP-Β-L-fucoseHMDB
Guanosine 5'-diphosphate L-fucoseHMDB
Guanosine 5'-diphospho-fucoseHMDB
Guanosine 5'-diphosphofucoseHMDB
Guanosine 5’-diphosphate L-fucoseHMDB
Guanosine 5’-diphospho-fucoseHMDB
Guanosine 5’-diphosphofucoseHMDB
GDP-L-fucoseHMDB
Predicted Properties
PropertyValueSource
Water Solubility7.04 g/LALOGPS
logP-1.7ALOGPS
logP-4.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area307.2 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity116.97 m³·mol⁻¹ChemAxon
Polarizability48.22 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC16H25N5O15P2
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]({[(3S,4R,5S,6S)-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)/t4-,5+,7+,8+,9+,10+,11-,14+,15?/m0/s1
InChI KeyLQEBEXMHBLQMDB-QIXZNPMTSA-N
Isomeric SMILESC[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@H](O)[C@@H]1O
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 Descriptors
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGDP-β-L-fucose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05bf-6985780000-f2b6a0fdececb1ffd409Spectrum
Predicted GC-MSGDP-β-L-fucose, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-6173159000-1cf7c64a7a19bbd73e28Spectrum
Predicted GC-MSGDP-β-L-fucose, "GDP-L-fucose,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGDP-β-L-fucose, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0910420000-6f2823064a15be7fc9a82015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0910000000-866d48af83abebf463392015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-8b884fd821ce0574d9f12015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ukl-2801490000-f519f8992a1d7307dde62015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1901000000-5004fbddcfb22c8ecd5f2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdl-3900000000-4c564cfa5a166417a5fa2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-2f459a27134486d5a1ca2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00c9-9401260000-e8773e96d7afecfae8152021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1501900000-343d428ef047e49497952021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0100090000-a6f771b381799c776be62021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-5922540000-c4c21e0fb882f03ef8632021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7x-9740000000-e90684222b98c6e2cd5a2021-09-23View Spectrum
NMRNot 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 IDHMDB0001095
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference