N-[(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-2-methoxy-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide

• ChemBase ID: 172291
• Molecular Formular: C21H37NO15
• Molecular Mass: 543.51618
• Monoisotopic Mass: 543.21631949
• SMILES: [C@H]1(C(O[C@H]([C@H]([C@H]1O)O)O[C@H]1[C@@H]([C@@H]([C@@H](O[C@H]1CO)OC)NC(=O)C)O[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)CO)O)O)O)C)O
• Canonical SMILES: OC[C@@H]1O[C@@H](OC)[C@H]([C@H]([C@@H]1O[C@@H]1OC(C)[C@H]([C@@H]([C@@H]1O)O)O)O[C@@H]1O[C@@H](CO)[C@@H]([C@@H]([C@@H]1O)O)O)NC(=O)C
• InChI: InChI=1S/C21H37NO15/c1-6-11(26)13(28)15(30)20(33-6)36-17-9(5-24)35-19(32-3)10(22-7(2)25)18(17)37-21-16(31)14(29)12(27)8(4-23)34-21/h6,8-21,23-24,26-31H,4-5H2,1-3H3,(H,22,25)/t6?,8-,9-,10-,11-,12+,13-,14+,15+,16-,17-,18-,19-,20+,21+/m1/s1
• InChIKey: GGCROZRVVJQWNN-QITCBKQVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-2-methoxy-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-2-methoxy-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide
• Synonyms: Methyl 2-Acetamido-2-deoxy-4-O-(α-L-fucopyranosyl)-3-O-(b-D- galactopyranosyl)-b-D-glucopyranoside, Gal1-b-3[Fuc1-α-4]GlcNAc1-b-O-Me; Lewis A Trisaccharide, Methyl Glycoside

Database IDs

• CAS Number: 186315-40-2
• PubChem SID: 164228201
• PubChem CID: 71749781

CALCULATED PROPERTIES

• Acid pKa: 11.7458315
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): -5.0722094
• LogD (pH = 7.4): -5.072228
• Log P: -5.0722094
• Molar Refractivity: 115.0588 cm^3
• Polarizability: 48.17995 Å^3
• Polar Surface Area: 246.32 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Colourless Solid
• Melting Point: 177-180°C dec.

Safety Information

• Storage Condition: -20°C Freezer

REFERENCES

• Dabelsteen, E., et al.: Cancer Research, 48, 181 (1988)
• Lasky, L.A.: Science, 258, 964 (1988)
• Mulligan, M.S., et al.: Nature, 364, 149 (1988)
• Mulligan, M.S., et al.: J. Exp. Med., 178, 623 (1988)
• Travis, J.: Science, 260, 906 (1993)