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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:36 UTC
Update Date2018-05-20 06:50:22 UTC
HMDB IDHMDB0002098
Secondary Accession Numbers
  • HMDB02098
Metabolite Identification
Common Name2-Fucosyllactose
Description2-Fucosyllactose (Fuc-a( 1->2)Galb(1->4)Glc) is an oligosaccharide first found in milk in the 1950s, and a well established isolation technique was found in 1972 (PMID: 5012321 ). It has been used as an acceptor substrate in assays of the blood group A and B gene specified glycosyltransferases since. (PMID 6894927 ).
Structure
Thumb
Synonyms
ValueSource
2'-FucosyllactoseMeSH
Chemical FormulaC18H32O15
Average Molecular Weight488.4377
Monoisotopic Molecular Weight488.174120354
IUPAC Name(2R,3R,4R,5R)-4-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2,3,5,6-tetrahydroxyhexanal
Traditional Name2-fucosyllactose
CAS Registry Number41263-94-9
SMILES
C[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@H](CO)[C@H](O)[C@@H]2O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C18H32O15/c1-5-9(24)12(27)14(29)17(30-5)33-16-13(28)11(26)8(4-21)31-18(16)32-15(7(23)3-20)10(25)6(22)2-19/h2,5-18,20-29H,3-4H2,1H3/t5-,6-,7+,8+,9+,10+,11-,12+,13-,14-,15+,16+,17-,18-/m0/s1
InChI KeyHWHQUWQCBPAQQH-BWRPKUOHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • Fatty acyl glycoside
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty alcohol
  • Beta-hydroxy aldehyde
  • Fatty acyl
  • Oxane
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Aldehyde
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility240 g/LALOGPS
logP-2.5ALOGPS
logP-6.1ChemAxon
logS-0.31ALOGPS
pKa (Strongest Acidic)11.61ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area256.29 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity100.63 m³·mol⁻¹ChemAxon
Polarizability45.41 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-076r-9103800000-bf203ba7cac67dfe883dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-9100136000-b95c034be8720992a749View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-020r-0907600000-03fe090eca1ada6cf5f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gi-3915000000-7500b0190da9d69087e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-6931000000-f206622ecfe42d8880c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-6419800000-a1898b2ba544b6b677e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-4914100000-e80269c3ceed657132ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-7911000000-4f26b060a48ff6151bf1View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Breast Milk
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified2500 +/- 1700 uMAdult (>18 years old)Female
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019340
KNApSAcK IDNot Available
Chemspider ID149055
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound170484
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceAlbermann C; Piepersberg W; Wehmeier U F Synthesis of the milk oligosaccharide 2'-fucosyllactose using recombinant bacterial enzymes. Carbohydrate research (2001), 334(2), 97-103.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kobata A, Ginsburg V: Oligosaccharides of human milk. 3. Isolation and characterization of a new hexasaccharide, lacto-N-hexaose. J Biol Chem. 1972 Mar 10;247(5):1525-9. [PubMed:5012321 ]
  2. Anderson A, Donald AS: Improved method for the isolation of 2' fucosyllactose from human milk. J Chromatogr. 1981 Jun 26;211(1):170-4. [PubMed:6894927 ]