(2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 173228
• Molecular Formular: C12H21NO9
• Molecular Mass: 323.29644
• Monoisotopic Mass: 323.12163126
• SMILES: [C@@H]1([C@@H]([C@@H](C[C@@](O1)(C(=O)O)OC)O)NC(=O)C)[C@@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@](OC)(C[C@H]([C@H]1NC(=O)C)O)C(=O)O)O)O
• InChI: InChI=1S/C12H21NO9/c1-5(15)13-8-6(16)3-12(21-2,11(19)20)22-10(8)9(18)7(17)4-14/h6-10,14,16-18H,3-4H2,1-2H3,(H,13,15)(H,19,20)/t6-,7+,8+,9+,10+,12+/m0/s1
• InChIKey: NJRVVFURCKKXOD-MIDKXNQYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: N-Acetyl-2-O-methyl-α-neuraminic Acid; 2-O-Methyl-N-acetyl-α-neuraminic Acid; N-Acetyl-α-neuraminic Methyl Glycoside; 2α-Methoxysialic Acid; 2-O-Methyl-α-D-N-acetylneuraminic Acid

Database IDs

• CAS Number: 50930-22-8
• PubChem SID: 164229138
• PubChem CID: 446069

CALCULATED PROPERTIES

• Acid pKa: 3.0656354
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -5.3233356
• LogD (pH = 7.4): -6.387094
• Log P: -2.920811
• Molar Refractivity: 68.5326 cm^3
• Polarizability: 28.118418 Å^3
• Polar Surface Area: 165.78 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 113-115°C

Safety Information

• Storage Condition: Hygroscopic, Store under Inert atmosphere -20°C Freezer
• Storage Warning: Moisture, Temperature Sensitive

DETAILS

Toronto Research Chemicals - M275400

A model compound for studies of binding of influenza virus hemagglutinin and metal ions.

REFERENCES

• Sauter, N.K., et al.: Biochemistry, 28, 8388 (1989)
• Sharon, N., et al.: Science, 246, 227 (1989)
• Nagy, J.O., et al.: J. Med. Chem., 35 (1989)
• (1989)
• Knibbs, R.N., et al.: J. Biol. Chem., 268 (1989)
• 18524 (1993)