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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:36 UTC
Update Date2022-09-22 18:34:16 UTC
HMDB IDHMDB0002094
Secondary Accession Numbers
  • HMDB02094
Metabolite Identification
Common Name3-Fucosyllactose
Description3-Fucosyllactose is a milk oligosaccharide isolated in 1958 (PMID: 13546862 ), and that was also isolated for the first time from the urine of a blood group O, nonsecretor, woman during pregnancy and lactation in 1977 (PMID: 838696 ). Is resistant to enzymic hydrolysis in the gastrointestinal tract of the infant; it is postulated that they reach the large intestine where they serve as substrates for bacterial metabolism. (PMID 10837303 ).
Structure
Thumb
Synonyms
ValueSource
3-O-FucosyllactoseMeSH
3'-FucosyllactoseHMDB, MeSH
O-6-Deoxy-a-L-galactopyranosyl-(1->3)-O-[b-D-galactopyranosyl-(1->4)]- D-glucoseHMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[b-D-galactopyranosyl-(1->4)]- D-glucoseHMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[b-delta-galactopyranosyl-(1->4)]- D-glucoseHMDB
Chemical FormulaC18H32O15
Average Molecular Weight488.4377
Monoisotopic Molecular Weight488.174120354
IUPAC Name(2S,3S,4R,5S,6S)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-6-methyloxane-3,4,5-triol
Traditional Name3-fucosyllactose
CAS Registry Number41312-47-4
SMILES
C[C@@H]1O[C@@H](O[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)[C@@H]2O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C18H32O15/c1-4-7(21)9(23)12(26)17(29-4)33-15-8(22)5(2-19)31-18(13(15)27)32-14-6(3-20)30-16(28)11(25)10(14)24/h4-28H,2-3H2,1H3/t4-,5+,6+,7+,8-,9+,10+,11+,12-,13+,14+,15-,16?,17-,18-/m0/s1
InChI KeyAUNPEJDACLEKSC-ZAYDSPBTSA-N
Chemical Taxonomy
Description 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
  • O-glycosyl compound
  • Glycosyl compound
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Breast Milk
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified2100 +/- 1200 uMAdult (>18 years old)Female
Normal
details
Breast MilkDetected and Quantified2702.494(102.367-8025.588) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022842
KNApSAcK IDNot Available
Chemspider ID141824
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound161460
PDB IDNot Available
ChEBI ID90065
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Engfer MB, Stahl B, Finke B, Sawatzki G, Daniel H: Human milk oligosaccharides are resistant to enzymatic hydrolysis in the upper gastrointestinal tract. Am J Clin Nutr. 2000 Jun;71(6):1589-96. [PubMed:10837303 ]
  2. Hallgren P, Lindberg BS, Lundblad A: Quantitation of some urinary oligosaccharides during pregnancy and lactation. J Biol Chem. 1977 Feb 10;252(3):1034-40. [PubMed:838696 ]
  3. KUHN R: [Oligosaccharides of milk]. Bull Soc Chim Biol (Paris). 1958;40(2-3):297-314. [PubMed:13546862 ]