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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-24 12:52:32 UTC
Update Date2022-09-22 18:34:19 UTC
HMDB IDHMDB0006582
Secondary Accession Numbers
  • HMDB06582
Metabolite Identification
Common NameLewis a trisaccharide
DescriptionLewis a trisaccharide is a fucosyloligosaccharide present in human milk and colostrum. Human colostrum is known to be important for the protection of infants against infection by pathogenic microorganisms. This protection is thought to be due, partially, to various neutral and acidic oligosaccharides that are present in colostrum and milk. Moderate-to-severe diarrhea of all causes occurs less often in infants whose milk contains high levels of total 2-linked fucosyloligosaccharides as a percent of milk oligosaccharide. The trisaccharide Lewis a trisaccharide is identical with the structure for the specific determinant in Lea substance, and strongly inhibits the agglutination of Lea erythrocytes by a human anti-Lea serum. (PMID: 15343178 , 17375110 , 12568665 , 2503806 ; 3809884; 6809837; 6880139; 7701811; 8662894; 8914840; 8943285).
Structure
Data?1582752393
Synonyms
Chemical FormulaC20H35NO15
Average Molecular Weight529.4896
Monoisotopic Molecular Weight529.200669455
IUPAC NameN-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide
Traditional NameN-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide
CAS Registry Number56570-03-7
SMILES
[H][C@@](O[C@@H]1O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]1O)([C@H](O)CO)[C@]([H])(O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@@H](NC(C)=O)C=O
InChI Identifier
InChI=1S/C20H35NO15/c1-6-11(27)13(29)15(31)19(33-6)36-18(9(26)4-23)17(8(3-22)21-7(2)25)35-20-16(32)14(30)12(28)10(5-24)34-20/h3,6,8-20,23-24,26-32H,4-5H2,1-2H3,(H,21,25)/t6-,8-,9+,10+,11+,12-,13+,14-,15-,16+,17+,18+,19-,20-/m0/s1
InChI KeyHHQLEBOUBWWITP-MBKDEEHCSA-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
  • Glycosyl compound
  • O-glycosyl compound
  • Amino saccharide
  • Monosaccharide
  • Oxane
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Acetal
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Carboxylic acid derivative
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aldehyde
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
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
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 IDFDB023984
KNApSAcK IDNot Available
Chemspider ID30776578
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477858
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMakimura, Yutaka; Ishida, Hideharu; Kiso, Makoto; Hasegawa, Akira. Synthetic studies of sialoglycoconjugates. 93. Synthetic studies on tumor-associated antigens: efficient syntheses of Lea and sialyl-Lea oligosaccharides, and their deaminated analogs. ChemInform 28(35) · August 2010
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Morrow AL, Ruiz-Palacios GM, Altaye M, Jiang X, Guerrero ML, Meinzen-Derr JK, Farkas T, Chaturvedi P, Pickering LK, Newburg DS: Human milk oligosaccharides are associated with protection against diarrhea in breast-fed infants. J Pediatr. 2004 Sep;145(3):297-303. [PubMed:15343178 ]
  2. Asakuma S, Urashima T, Akahori M, Obayashi H, Nakamura T, Kimura K, Watanabe Y, Arai I, Sanai Y: Variation of major neutral oligosaccharides levels in human colostrum. Eur J Clin Nutr. 2008 Apr;62(4):488-94. Epub 2007 Mar 21. [PubMed:17375110 ]
  3. Sumiyoshi W, Urashima T, Nakamura T, Arai I, Saito T, Tsumura N, Wang B, Brand-Miller J, Watanabe Y, Kimura K: Determination of each neutral oligosaccharide in the milk of Japanese women during the course of lactation. Br J Nutr. 2003 Jan;89(1):61-9. [PubMed:12568665 ]
  4. Ford DS, Condon JA, Bacon J, Richards VL, Kronenberg H: A family exhibiting the cis-AB genotype. Pathology. 1989 Jan;21(1):23-6. [PubMed:2503806 ]