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

• ChemBase ID: 158903
• Molecular Formular: C14H25NO11
• Molecular Mass: 383.3484
• Monoisotopic Mass: 383.14276063
• SMILES: [C@H]1([C@@H]([C@@H](C(O[C@H]1CO)O)O)O)O[C@H]1O[C@H]([C@H]([C@@H]([C@@H]1NC(=O)C)O)O)CO
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@H]([C@H]1O[C@H]1O[C@@H](CO)[C@H]([C@@H]([C@@H]1NC(=O)C)O)O)O)O
• InChI: InChI=1S/C14H25NO11/c1-4(18)15-7-9(20)8(19)5(2-16)25-14(7)26-12-6(3-17)24-13(23)11(22)10(12)21/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8-,9-,10-,11-,12+,13?,14-/m1/s1
• InChIKey: DRHGSSXSNNHAAL-VXTIANRJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2R,3R,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2R,3R,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]acetamide
• Synonyms: 4-O-[2-(Acetylamino)-2-deoxy-α-D-glucopyranosyl]-D-galactose; α-D-GlcNAc-α-(1-4)-D-Gal; GlcNAc-α-(1-4)-Gal; 4-O-(2-Acetamido-2-deoxy-α-D-glucopyranosyl)-D-galactose

Database IDs

• CAS Number: 76909-76-7
• PubChem SID: 162253038
• PubChem CID: 71312733

CALCULATED PROPERTIES

• Acid pKa: 11.242464
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.9914107
• LogD (pH = 7.4): -4.991472
• Log P: -4.9914103
• Molar Refractivity: 79.438 cm^3
• Polarizability: 33.212086 Å^3
• Polar Surface Area: 198.4 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A157280

An N-acetylglucosamine derivative as antibacterial against Helicobacter pylori.

REFERENCES

• Hatheway, C., et al.: Clin. Microbiol. Rev., 3, 66 (1990)
• Borriello, S., et al.: Clin. Infect. Dis., 20, S242 (1990)
• Ishihara, K., et al.: Biochem. J., 318, 409 (1990)