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

• ChemBase ID: 161356
• Molecular Formular: C21H31NO11
• Molecular Mass: 473.47094
• Monoisotopic Mass: 473.18971082
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)O[C@H]1[C@@H]([C@@H](O[C@@H]([C@H]1NC(=O)C)OCc1ccccc1)CO)O)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@H](OCc2ccccc2)[C@H]([C@H]([C@@H]1O)O[C@@H]1O[C@@H](CO)[C@@H]([C@@H]([C@@H]1O)O)O)NC(=O)C
• InChI: InChI=1S/C21H31NO11/c1-10(25)22-14-19(33-21-18(29)17(28)15(26)12(7-23)32-21)16(27)13(8-24)31-20(14)30-9-11-5-3-2-4-6-11/h2-6,12-21,23-24,26-29H,7-9H2,1H3,(H,22,25)/t12-,13-,14-,15+,16-,17+,18-,19-,20+,21+/m1/s1
• InChIKey: MYDRTQFLXCNCAG-DWFGKLAWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• Synonyms: Phenylmethyl 2-(Acetylamino)-2-deoxy-3-O-β-D-galactopyranosyl-α-D-glucopyranoside; Gal1-β-3GlcNAc-α-OBn; Benzyl 2-Acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-glucopyranoside

Database IDs

• CAS Number: 50692-66-5
• PubChem SID: 162255491
• PubChem CID: 71313747

CALCULATED PROPERTIES

• Acid pKa: 11.937178
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -2.6238108
• LogD (pH = 7.4): -2.6238225
• Log P: -2.6238105
• Molar Refractivity: 108.8018 cm^3
• Polarizability: 44.48356 Å^3
• Polar Surface Area: 187.4 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 222-228°C

Safety Information

• Storage Condition: -20°C Freezer

REFERENCES

• Gambert, U., et al.: Bioorg. Med. Chem., 5, 1285 (1997)