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

• ChemBase ID: 173230
• Molecular Formular: C13H23NO9
• Molecular Mass: 337.32302
• Monoisotopic Mass: 337.13728132
• SMILES: [C@@H]1(C([C@@H](C[C@](O1)(C(=O)OC)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](C1NC(=O)C)O)C(=O)OC)O)O
• InChI: InChI=1S/C13H23NO9/c1-6(16)14-9-7(17)4-13(22-3,12(20)21-2)23-11(9)10(19)8(18)5-15/h7-11,15,17-19H,4-5H2,1-3H3,(H,14,16)/t7-,8+,9?,10+,11+,13-/m0/s1
• InChIKey: JKTJXQQVMKZKQA-IIFQRTFMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,4S,6R)-5-acetamido-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,4S,6R)-5-acetamido-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• Synonyms: 2-O-Methyl-β-D-N-acetylneuraminic Acid, Methyl Ester

Database IDs

• CAS Number: 6730-43-4
• PubChem SID: 164229140
• PubChem CID: 71750170

CALCULATED PROPERTIES

• Acid pKa: 12.620022
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.7749176
• LogD (pH = 7.4): -2.7749195
• Log P: -2.774917
• Molar Refractivity: 73.3017 cm^3
• Polarizability: 30.149857 Å^3
• Polar Surface Area: 154.78 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Hot Methanol
• Apperance: White Solid
• Melting Point: 115-125°C

DETAILS

Toronto Research Chemicals - M275410

A model compound for studies of binding of influenza virus hemaglutinin 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)