methyl (2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate

• ChemBase ID: 159098
• Molecular Formular: C12H19NO8
• Molecular Mass: 305.28116
• Monoisotopic Mass: 305.11106657
• SMILES: C1=C(O[C@H]([C@@H]([C@@H]1O)NC(=O)C)[C@H]([C@@H](CO)O)O)C(=O)OC
• Canonical SMILES: OC[C@H]([C@@H]([C@@H]1OC(=C[C@H]([C@H]1NC(=O)C)O)C(=O)OC)O)O
• InChI: InChI=1S/C12H19NO8/c1-5(15)13-9-6(16)3-8(12(19)20-2)21-11(9)10(18)7(17)4-14/h3,6-7,9-11,14,16-18H,4H2,1-2H3,(H,13,15)/t6-,7+,9+,10+,11+/m0/s1
• InChIKey: SPILYXOSOLBQAQ-CNYIRLTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• IUPAC Traditional name: methyl (4S,5R,6R)-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-5,6-dihydro-4H-pyran-2-carboxylate
• Synonyms: D-glycero-D-galacto-Non-2-enonic acid, 5-(acetylamino)-2,6-anhydro-3,5-dideoxy-, methyl ester; 2,3-Dehydro-N-acetylneuraminic acid methyl ester; N-Acetyl-2,3-dehydro-2-deoxyneuraminic Acid Methyl Ester

Database IDs

• CAS Number: 25875-99-4
• PubChem SID: 162253233
• PubChem CID: 10935625

CALCULATED PROPERTIES

• Acid pKa: 12.529093
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -3.3089252
• LogD (pH = 7.4): -3.3089275
• Log P: -3.3089247
• Molar Refractivity: 68.8798 cm^3
• Polarizability: 27.317547 Å^3
• Polar Surface Area: 145.55 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Crystalline Solid
• Melting Point: 215-217°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A172190

Inhibitor of bacterial, animal and viral sialidases.

REFERENCES

• Schauer, R.: Adv. Carbohydr. Chem. Biochem., 40, 131 (1982)
• Schreiner, E. & Schauer, R.: Carbohydrate Res., 216, 61 (1991)