Lewis x Trisaccharide
Basic information
- CAS
71208-06-5- Standard SMILES
CC(=O)N[C@@H](C=O)[C@@H](O[C@@H]1O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]1O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)CO- InChIKey
ZAFUNKXZZPSTLA-MBKDEEHCSA-N- Molecular formula
- C20H35NO15
- Average molar mass
- 529.5 g/mol
- Monoisotopic mass
- 529.20066941
Names & identifiers
- Preferred name
- Lewis x Trisaccharide
- IUPAC
- 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]oxyhexan-2-yl]acetamide
- English name
- LEWIS X TRISACCHARIDE
- Molecular formula
- C20H35NO15
- Molecular weight
- 529.49
Names & synonyms
Lewis x Trisaccharide71208-06-5N-[(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]oxyhexan-2-yl]acetamideLex triLexN-((2R,3R,4R,5R)-5,6-Dihydroxy-1-oxo-4-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)hexan-2-yl)acetamideCD 15 antigenLEWISXWR4ZB0LRW93-Fucosyl-N-acetylactosamineSCHEMBL29130815DTXSID80991523
Show more names
Lex TrisaccharideLewis X (LeX) triaoseGalβ1-4(Fucα1-3)GlcNAcLewis X (LeX) SSEA-1/CD15Lewis x (Lex) triose (>90% NMR)
HY-N10534GAL1-B-4[FUC1-A-3]GLCNACGal|?1, 4(Fuc| cent1, 3)GlcNAcGAL-BETA1,4(FUC-ALPHA1,3)GLCNACCS-0610609NS00127111F77805Lex Trisaccharide, alpha-L-Fuc-(1-3)-[beta-D-Gal-(1-4)]-D-GlcNAc
Properties
Computed structural properties
- XLogP
- -6.1
- Topological polar surface area
- 265 Ų
- Hydrogen bond donors
- 10
- Hydrogen bond acceptors
- 15
- Rotatable bonds
- 11
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 715
Experimental & physicochemical properties
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 155 · 155-156°C
- Boiling point
- 977.193 · 977.193±65.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.606 · 1.606±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- White solid
- pka
- 12.825 · 12.825±0.70(predicted)
- color
- Off-White to Pale Yellow
- Water Solubility
- 5 mg/mL · water: 5mg/mL
- Stability
- Hygroscopic
- InChIKey
- ZAFUNKXZZPSTLA-MBKDEEHCSA-N
- UNSPSC Code
- 12352201 · 12352201
- Symbol(GHS)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Applications
UsesLewis X and related compounds bind to the selectins and act as anti-inflammatory agents.
UsesLewisx tumor-associated trisaccharide antigen, E- and P-selectin ligand, anti-inflammatory agent
General DescriptionEnzymatically prepared trisaccharide. Shown to act as an anti-inflammatory agent by competitive binding to selectins.
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Compound notes
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