3-O-alpha-L-Fucopyranosyl-D-glucose (CHEM036199)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:18:43 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036199
Identification
Common Name3-O-alpha-L-Fucopyranosyl-D-glucose
ClassSmall Molecule
Description3-O-alpha-L-Fucopyranosyl-D-glucose is a fucosylated oligosaccharide specific to human milk that form part of the innate immune system. contributing to the protection by breast-feeding of the newborn against enteric diseases through the mechanism of preventing the attachment of pathogenic bacteria to the duodenual epithelium. (PMID 1579031).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-O-(6-Deoxy-alpha-L-galactopyranosyl)- D-glucoseHMDB
3-O-alpha-L-Fucopyranosyl-D-glucoseHMDB
3-O-alpha-L-Fucopyranosyl-delta-glucoseHMDB
3-O-a-L-Fucopyranosyl-D-glucoseGenerator
3-O-Α-L-fucopyranosyl-D-glucoseGenerator
Chemical FormulaC12H22O10
Average Molecular Mass326.297 g/mol
Monoisotopic Mass326.121 g/mol
CAS Registry Number56822-52-7
IUPAC Name(2R,4R)-2,4,5,6-tetrahydroxy-3-{[(2S,3S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexanal
Traditional Name(2R,4R)-2,4,5,6-tetrahydroxy-3-{[(2S,3S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexanal
SMILESCC1O[C@@H](OC([C@@H](O)C=O)[C@H](O)C(O)CO)[C@@H](O)C(O)C1O
InChI IdentifierInChI=1S/C12H22O10/c1-4-7(17)9(19)10(20)12(21-4)22-11(6(16)3-14)8(18)5(15)2-13/h3-13,15-20H,2H2,1H3/t4?,5?,6-,7?,8+,9?,10-,11?,12-/m0/s1
InChI KeyWFLGVJKIXANXQV-CJVZSHCUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Disaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Fatty alcohol
  • Oxane
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aldehyde
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility216 g/LALOGPS
logP-2.2ALOGPS
logP-4.3ChemAxon
logS-0.18ALOGPS
pKa (Strongest Acidic)11.63ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity68.22 m³·mol⁻¹ChemAxon
Polarizability30.38 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aos-9273000000-ec95f81eaa9248e3d40dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00di-4101029000-db63e7852c62da20a8abSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bw9-1916000000-39416eeae50a13a70f0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08gi-5900000000-4aed1c81e58e01f174dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-9600000000-530d0e079e50a204c5bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0cg3-7793000000-5cf8354c214843d41cf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-5931000000-99f88726f4243f3661b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-9700000000-34215cca6c597371175eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004m-4389000000-91932607a5c34ee76a2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vn-6921000000-0cf03aef522636b140a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9100000000-1ffeca759e99ece2b9a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bt9-0935000000-2046baf2d5abcb317f61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022c-8900000000-22a35255a2741c1c6fbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9400000000-8fbcd220a856ecada0a3Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006701
FooDB IDFDB024033
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35016017
ChEBI ID168871
PubChem Compound ID53477882
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Ajisaka, Katsumi; Shirakabe, Mayumi. Regioselective synthesis of a-L-fucosyl-containing disaccharides by use of a-L-fucosidases of various origins. Carbohydrate Research (1992), 224 291-9.
2. DiCioccio RA, Barlow JJ, Matta KL: Substrate specificity and other properties of alpha-L-fucosidase from human serum. J Biol Chem. 1982 Jan 25;257(2):714-8.
3. Bachner M, Alain T: [Future of psychiatry--a medical specialty or an interdisciplinary activity?]. Lakartidningen. 1992 May 6;89(19):1652-3; discussion 1653-4.