N-[(4aR,6S,7R,8R,8aR)-6-(benzyloxy)-2-phenyl-8-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]acetamide

• ChemBase ID: 161354
• Molecular Formular: C28H35NO11
• Molecular Mass: 561.5776
• Monoisotopic Mass: 561.22101095
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)O[C@H]1[C@@H]2[C@H](O[C@@H]([C@H]1NC(=O)C)OCc1ccccc1)COC(O2)c1ccccc1)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](O[C@H]2[C@H]3OC(OC[C@H]3O[C@@H]([C@H]2NC(=O)C)OCc2ccccc2)c2ccccc2)[C@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C28H35NO11/c1-15(31)29-20-25(40-28-23(34)22(33)21(32)18(12-30)37-28)24-19(14-36-26(39-24)17-10-6-3-7-11-17)38-27(20)35-13-16-8-4-2-5-9-16/h2-11,18-28,30,32-34H,12-14H2,1H3,(H,29,31)/t18-,19-,20-,21+,22+,23-,24+,25-,26?,27+,28+/m1/s1
• InChIKey: QXRLFXLKFXJEJD-ONYJJJNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(4aR,6S,7R,8R,8aR)-6-(benzyloxy)-2-phenyl-8-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• IUPAC Traditional name: N-[(4aR,6S,7R,8R,8aR)-6-(benzyloxy)-2-phenyl-8-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• Synonyms: Phenylmethyl 2-(Acetylamino)-2-deoxy-3-O-β-D-galactopyranosyl-4,6-O-(phenylmethylene)-α-D-galactopyranoside; Benzyl 2-Acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-4,6-benzylidene-α-D-galactoside

Database IDs

• CAS Number: 90754-58-8
• PubChem SID: 162255489
• PubChem CID: 57369910

CALCULATED PROPERTIES

• Acid pKa: 11.983987
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 0.54126847
• LogD (pH = 7.4): 0.54125804
• Log P: 0.5412688
• Molar Refractivity: 135.6854 cm^3
• Polarizability: 55.203575 Å^3
• Polar Surface Area: 165.4 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Water
• Apperance: Pale-Brown Solid

REFERENCES

• Xia, J., et al.: Bioorg. Med. Chem., 10, 3673 (2002)