Record Information
Version1.0
Creation date2010-04-08 22:15:06 UTC
Update date2019-11-26 03:19:06 UTC
Primary IDFDB020543
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Fucose
DescriptionA constituent of the polysaccharides obtained from gum tragacanthand is) also found in glycoproteins obtained from milk Fucose is a hexose deoxy sugar with the chemical formula C6H12O5. It is found on N-linked glycans on the mammalian, insect and plant cell surface, and is the fundamental sub-unit of the fucoidan polysaccharide. Alpha1?3 linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy.; Fucose is a hexose sugar with the chemical formula C6H12O5. It is found on N-linked glycans on the mammalian and plant cell surface. Fucose is secreted in urine when the liver is damaged. Alpha1->3 linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy. Two structural features distinguish fucose from other six-carbon sugars present in mammals: the lack of a hydroxyl group on the carbon at the 6-position (C-6) and the L-configuration. In fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars.
CAS Number2438-80-4
Structure
Thumb
Synonyms
SynonymSource
6-Deoxy-L-galactoseChEBI
(-)-FucoseHMDB
(-)-L-FucoseHMDB
6-Deoxy-L-galactopyranoseHMDB
6-DesoxygalactoseHMDB
6-Methyloxane-2,3,4,5-tetrolHMDB
6-Methyltetrahydropyran-2,3,4,5-tetraolHMDB
FucoseHMDB
IsodulcitHMDB
L-(-)-FucoseHMDB
L-FucopyranoseHMDB
L-GalactomethyloseHMDB
RhodeoseHMDB
alpha FucoseHMDB
alpha-FucoseHMDB
DeoxygalactoseHMDB
(-)-fucosebiospider
(-)-l-fucosebiospider
6-Deoxy-beta-galactosebiospider
6-Deoxy-D-galactopyranosebiospider
6-Deoxy-delta-galactopyranosebiospider
6-Deoxy-L-beta-galactosebiospider
6-methyloxane-2,3,4,5-tetrolbiospider
6-methyltetrahydropyran-2,3,4,5-tetraolbiospider
D-threo-aldosebiospider
FUCbiospider
Fucopyranose, L- (7CI)biospider
Fucose, l-biospider
L-(-)-fucosebiospider
L-fucopyranosebiospider
L-fucosebiospider
L-galactomethylosebiospider
L-galactopyranose, 6-deoxy-biospider
L-Galactopyranose, 6-deoxy- (9CI)biospider
L-Galactose, 6-deoxy-biospider
Predicted Properties
PropertyValueSource
logP-1.9ChemAxon
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.38 m³·mol⁻¹ChemAxon
Polarizability15.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H36O15
IUPAC name(3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol
InChI IdentifierInChI=1S/3C6H12O5/c1-2(7)5-3(8)4(9)6(10)11-5;1-2-3(7)4(8)5(9)6(10)11-2;1-3(8)5(10)6(11)4(9)2-7/h2*2-10H,1H3;2-6,8-11H,1H3
InChI KeyLSOFIIQFGYOXNZ-UHFFFAOYSA-N
Isomeric SMILESCC(O)C(O)C(O)C(O)C=O.CC(O)C1OC(O)C(O)C1O.CC1OC(O)C(O)C(O)C1O
Average Molecular Weight492.4694
Monoisotopic Molecular Weight492.205420482
Classification
Description Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 43.90%; H 7.37%; O 48.73%DFC
Melting PointMp 145° (140-141°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]17D -124 -> -76 (c, 2.0 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-ff79aee2e9ac3a4f53c8Spectrum
GC-MS, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-23d1bd654495aefbf615Spectrum
GC-MS, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-ff79aee2e9ac3a4f53c8Spectrum
GC-MS, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-23d1bd654495aefbf615Spectrum
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4j-9500000000-cfa9e0d8f1f20b29e5d8Spectrum
Predicted GC-MS, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002r-9346400000-7524daf3b04caf0c441aSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uxr-1900000000-78487d681dfa23efe227Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-c8f3e40cfff39fe7c419Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-6752b85bef2dc57dfb8eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-5daf054ff3eb9127d3caSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-f7729c93b964e01cb774Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-9000000000-2c46a67befe14c31d7a9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-86321b083a11f93bb55bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-5900000000-2accd457fe7b58b9b032Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-9e349c8fad042f6a3e99Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID16190
ChEMBL IDCHEMBL469449
KEGG Compound IDC01019
Pubchem Compound ID17106
Pubchem Substance IDNot Available
ChEBI ID18287
Phenol-Explorer IDNot Available
DrugBank IDDB03283
HMDB IDHMDB00174
CRC / DFC (Dictionary of Food Compounds) IDHCR06-X:MTL87-K
EAFUS IDNot Available
Dr. Duke IDFUCOSE
BIGG ID36636
KNApSAcK IDC00035100
HET ID1AH1
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDL-Fucose
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
AcetylcholinesteraseACHEP22303
Plasma alpha-L-fucosidaseFUCA2Q9BTY2
Tissue alpha-L-fucosidaseFUCA1P04066
L-fucose kinaseFUKQ8N0W3
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064 map00051
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.