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

• ChemBase ID: 158907
• Molecular Formular: C14H25NO11
• Molecular Mass: 383.3484
• Monoisotopic Mass: 383.14276063
• SMILES: O1C([C@H]([C@H]([C@@H]([C@@H]1CO)O)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1NC(=O)C)O)O)CO)O
• Canonical SMILES: OC[C@@H]1OC(O)[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/C14H25NO11/c1-4(18)15-7-10(21)8(19)6(3-17)25-14(7)26-12-11(22)9(20)5(2-16)24-13(12)23/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: KGSIOYQZUFTKHO-DLDFRZNISA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 34621-73-3
• PubChem SID: 162253042
• PubChem CID: 10221549

CALCULATED PROPERTIES

• Acid pKa: 11.255271
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.9914107
• LogD (pH = 7.4): -4.99147
• 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

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 141-143°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A158175

A common oligosaccharide that inhibits the adherence of typical and atypical respiratory pathogens.

REFERENCES

• Bryan, R., et al.: J. Infect. Dis., 179, 1449 (1999)
• Chiu, C., et al.: Microbiology, 147, 2651 (1999)
• Ahmed, K., et al.: Med. Microbiol. Immunol., 191, 5 (1999)
• Ariel, N., et al.: Infect. Immun., 71, 4563 (1999)