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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-24 10:32:53 UTC
Update Date2021-09-14 15:18:17 UTC
HMDB IDHMDB0006568
Secondary Accession Numbers
  • HMDB06568
Metabolite Identification
Common NameLewis X trisaccharide
DescriptionLewis X trisaccharide is a common oligosaccharide involved in the terminal glycosylation of oligosaccharide chains of glycoconjugates and as such play a major role in the antigenic properties of cell surfaces and in the changing carbohydrates profiles that occur on cell maturation and in malignancy. Lewis X present in human milk can bind to DC-specific ICAM3-grabbing non-integrin and thereby prevent the capture and subsequent transfer of HIV-1 to CD4+ T lymphocytes. The presence of such a DC-specific ICAM3-grabbing non-integrin-binding molecule in human milk may both influence antigenic presentation and interfere with pathogen transfer in breastfed infants. Lewis X is a promising urine marker for bladder cancer surveillance in urothelial cell carcinoma patients. (PMID: 11278542 ; 11300757; 15184372; 15242599; 15845541; 16239964; 16773661; 9490204, 16217395).
Structure
Data?1582752392
Synonyms
ValueSource
3-Fucosyl-N-acetyllactosamineHMDB
FALHMDB
Lewis XHMDB
LexHMDB
Lex triHMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[beta-D-galactopyranosyl-(1->4)]-2-(acetylamino)-2-deoxy-D-glucoseHMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[beta-delta-galactopyranosyl-(1->4)]-2-(acetylamino)-2-deoxy-delta-glucoseHMDB
N-[(2R,3R,4R,5R)-5,6-Dihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]ethanimidateGenerator, HMDB
Chemical FormulaC20H35NO15
Average Molecular Weight529.4896
Monoisotopic Molecular Weight529.200669455
IUPAC NameN-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(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-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide
CAS Registry Number71208-06-5
SMILES
[H][C@@](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)([C@H](O)CO)[C@]([H])(O[C@@H]1O[C@@H](C)[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)35-17(8(3-22)21-7(2)25)18(9(26)4-23)36-20-16(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 KeyZAFUNKXZZPSTLA-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 LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023976
KNApSAcK IDNot Available
Chemspider ID2299860
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3035680
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceJacquinet, Jean Claude; Sinay, Pierre. Synthesis of blood-group substances. Part 7. Synthesis of the branched trisaccharide O-a-L-fucopyranosyl-(1®3)-[O-b-D-galactopyranosyl-(1®4)]-2-acetamido-2-deoxy-D-glucopyranose. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1979), (2), 314-18.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Cao Z, Zhao Z, Mohan R, Alroy J, Stanley P, Panjwani N: Role of the Lewis(x) glycan determinant in corneal epithelial cell adhesion and differentiation. J Biol Chem. 2001 Jun 15;276(24):21714-23. Epub 2001 Mar 15. [PubMed:11278542 ]

Enzymes

General function:
Involved in sugar binding
Specific function:
Scavenger receptor that displays several functions associated with host defense. Promotes binding and phagocytosis of Gram-positive, Gram-negative bacteria and yeast. Mediates the recognition, internalization and degradation of oxidatively modified low density lipoprotein (oxLDL) by vascular endothelial cells. Binds to several carbohydrates including Gal-type ligands, D-galactose, L- and D-fucose, GalNAc, T and Tn antigens in a calcium-dependent manner and internalizes specifically GalNAc in nurse-like cells. Binds also to sialyl Lewis X or a trisaccharide and asialo-orosomucoid (ASOR). May also play a role in the clearance of amyloid beta in Alzheimer disease
Gene Name:
COLEC12
Uniprot ID:
Q5KU26
Molecular weight:
81514.7