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

• ChemBase ID: 172292
• Molecular Formular: C49H61NO15
• Molecular Mass: 904.00634
• Monoisotopic Mass: 903.40412026
• SMILES: [C@H]1([C@@H](O[C@H]([C@H]([C@H]1OCc1ccccc1)OCc1ccccc1)O[C@H]1[C@@H]([C@@H](C(O[C@H]1COCc1ccccc1)OC)NC(=O)C)O[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)CO)O)O)O)C)OCc1ccccc1
• Canonical SMILES: COC1O[C@@H](COCc2ccccc2)[C@H]([C@@H]([C@@H]1NC(=O)C)O[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]1OCc1ccccc1)OCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C49H61NO15/c1-30-42(58-26-33-18-10-5-11-19-33)45(59-27-34-20-12-6-13-21-34)46(60-28-35-22-14-7-15-23-35)49(61-30)64-43-37(29-57-25-32-16-8-4-9-17-32)63-47(56-3)38(50-31(2)52)44(43)65-48-41(55)40(54)39(53)36(24-51)62-48/h4-23,30,36-49,51,53-55H,24-29H2,1-3H3,(H,50,52)/t30-,36+,37+,38+,39-,40-,41+,42+,43+,44+,45+,46-,47?,48-,49-/m0/s1
• InChIKey: PRRHDWGPDCOFAR-ZNPYIMQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S,6R)-6-[(benzyloxy)methyl]-2-methoxy-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(3R,4R,5S,6R)-6-[(benzyloxy)methyl]-2-methoxy-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide
• Synonyms: Methyl 2-Acetamido-6-O-benzyl-2-deoxy-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-3-O-(b-D- galactopyranosyl)-b-D-glucopyranoside, Gal1-b-3[Fuc-2,3,4-bn-1-α-4]GlcNAc-6-bn-1-b-O-Me; Lewis A Trisaccharide, Methyl Glycoside Tetrabenzylether

Database IDs

• PubChem SID: 164228202
• PubChem CID: 71749782

CALCULATED PROPERTIES

• Acid pKa: 11.915661
• H Acceptors: 15
• H Donor: 5
• LogD (pH = 5.5): 4.398189
• LogD (pH = 7.4): 4.3981767
• Log P: 4.398189
• Molar Refractivity: 232.514 cm^3
• Polarizability: 93.652115 Å^3
• Polar Surface Area: 202.32 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 115-118°C

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)