N-(5,6-dihydroxy-1-oxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]hexan-2-yl)acetamide

• ChemBase ID: 131083
• Molecular Formular: C20H35NO15
• Molecular Mass: 529.4896
• Monoisotopic Mass: 529.20066943
• SMILES: CC1C(C(C(C(O1)OC(C(C=O)NC(=O)C)C(C(CO)O)OC1C(C(C(C(O1)CO)O)O)O)O)O)O
• Canonical SMILES: O=CC(C(C(C(CO)O)OC1OC(CO)C(C(C1O)O)O)OC1OC(C)C(C(C1O)O)O)NC(=O)C
• InChI: 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)
• InChIKey: ZAFUNKXZZPSTLA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(5,6-dihydroxy-1-oxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]hexan-2-yl)acetamide
• IUPAC Traditional name: N-(5,6-dihydroxy-1-oxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]hexan-2-yl)acetamide
• Synonyms: α-L-Fuc-(1→3)-[β-D-Gal-(1→4)]-D-GlcNAc; Lex Trisaccharide; Lewis-X trisaccharide

Database IDs

• CAS Number: 71208-06-5
• MDL Number: MFCD00214084
• PubChem SID: 162225361
• PubChem CID: 4169156

CALCULATED PROPERTIES

• Acid pKa: 11.3070545
• H Acceptors: 15
• H Donor: 10
• LogD (pH = 5.5): -6.3511577
• LogD (pH = 7.4): -6.3512096
• Log P: -6.351157
• Molar Refractivity: 111.7298 cm^3
• Polarizability: 46.409077 Å^3
• Polar Surface Area: 265.16 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - L5152

Biochem/physiol Actions
Lewis-X is a developmentally regulated antigen and has been suggested to be a tumor marker. At high concentrations, it inhibits P-selectin-mediated adhesion.
Other Notes
Lewis-X is the trisaccharide part of the sialyl-Lewis-X tetrasaccharide, the suggested ligand for P- and E-selectins.