N-[(2S,3R,4R,5S,6R)-6-(hydroxymethyl)-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]-5-{[(2S,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}oxan-3-yl]acetamide

• ChemBase ID: 172295
• Molecular Formular: C30H41NO17
• Molecular Mass: 687.64304
• Monoisotopic Mass: 687.23744886
• SMILES: O(c1ccc2c(c1)oc(=O)cc2C)[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)CO)O[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)CO)O)O)O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C)O)O)O)NC(=O)C
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3C)[C@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](CO)[C@@H]([C@@H]([C@@H]1O)O)O)O[C@@H]1O[C@@H](C)[C@H]([C@@H]([C@@H]1O)O)O)NC(=O)C
• InChI: InChI=1S/C30H41NO17/c1-10-6-18(35)44-15-7-13(4-5-14(10)15)43-28-19(31-12(3)34)27(48-29-24(40)22(38)20(36)11(2)42-29)26(17(9-33)46-28)47-30-25(41)23(39)21(37)16(8-32)45-30/h4-7,11,16-17,19-30,32-33,36-41H,8-9H2,1-3H3,(H,31,34)/t11-,16+,17+,19+,20+,21-,22+,23-,24-,25+,26+,27+,28+,29-,30-/m0/s1
• InChIKey: PVUZBLNDARHJPS-FIVSWNKTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-6-(hydroxymethyl)-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]-5-{[(2S,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}oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-6-(hydroxymethyl)-2-[(4-methyl-2-oxochromen-7-yl)oxy]-5-{[(2S,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}oxan-3-yl]acetamide
• Synonyms: 4-Methylumbelliferyl 2-Acetamido-2-deoxy-3-O-(α-L-fucopyranosyl)-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside; Gal1-b-4[Fuc1-α-3]GlcNAc-4-MU; Lewis X Trisaccharide, 4-Methylumbelliferyl Glycoside

Database IDs

• CAS Number: 359436-57-0
• PubChem SID: 164228205
• PubChem CID: 71749783

CALCULATED PROPERTIES

• Acid pKa: 11.685347
• H Acceptors: 16
• H Donor: 9
• LogD (pH = 5.5): -3.271676
• LogD (pH = 7.4): -3.271697
• Log P: -3.2716758
• Molar Refractivity: 154.3401 cm^3
• Polarizability: 63.025414 Å^3
• Polar Surface Area: 272.62 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Grey Solid
• Melting Point: >170°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - L395600

Lewis x and related compounds are ligands for P- and E-selectins. Lewis x is a developmentally regulated antigen and has been suggested to be a tumor marker. These compounds may also act as anti-inflammatory agents.

REFERENCES

• Lasky, L.A.: Science, 258, 964 (1992)
• Mulligan, M.S., et al.: Nature, 364, 149 (1992)
• Mulligan, M.S., et al.: J. Exp. Med., 178, 623 (1992)
• Travis, J.: Science, 260, 906 (1993)