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

• ChemBase ID: 161379
• 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)OCc1ccccc1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)CO)O)O)NC(=O)C)O)O
• Canonical SMILES: OC[C@@H]1O[C@H](OCc2ccccc2)[C@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](CO)[C@H]([C@@H]([C@@H]1NC(=O)C)O)O
• InChI: InChI=1S/C21H31NO11/c1-10(25)22-14-17(28)15(26)12(7-23)31-20(14)33-19-18(29)16(27)13(8-24)32-21(19)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: DMMHDVIDPISODO-DUDXSYDCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-2-{[(2S,3S,4S,5S,6R)-2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-2-{[(2S,3S,4S,5S,6R)-2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: GlcNAc(β1-2)Man(α1-)O-benzyl; Phenylmethyl 2-O-[2-(Acetylamino)-2-deoxy-D-glucopyranosyl]-α-D-mannopyranoside; Benzyl 2-O-[2-(Acetylamino)-2-deoxy-β-D-glucopyranosyl]-α-D-mannopyranoside

Database IDs

• CAS Number: 436853-00-8
• PubChem SID: 162255514
• PubChem CID: 71313759

CALCULATED PROPERTIES

• Acid pKa: 12.052651
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -2.6238108
• LogD (pH = 7.4): -2.6238194
• 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

DETAILS

Toronto Research Chemicals - B223150

A product formed from Benzyl α-D-mannopyranoside (B282000) by α-3-D-mannoside by the enzyme UDP-GlcNAc:α-3-D-mannoside β1,2-N-acetylglucosaminyltransferase I.2 in humans.

REFERENCES

• Zhang, W. et al.: Biochem. J., 361, 153 (2002)