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

• ChemBase ID: 159099
• Molecular Formular: C11H16NNaO8
• Molecular Mass: 313.23641
• Monoisotopic Mass: 313.07736076
• SMILES: C1=C(O[C@H](C([C@@H]1O)NC(=O)C)[C@@H]([C@@H](CO)O)O)C(=O)[O-].[Na+]
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1OC(=C[C@H](C1NC(=O)C)O)C(=O)[O-])O)O.[Na+]
• InChI: InChI=1S/C11H17NO8.Na/c1-4(14)12-8-5(15)2-7(11(18)19)20-10(8)9(17)6(16)3-13;/h2,5-6,8-10,13,15-17H,3H2,1H3,(H,12,14)(H,18,19);/q;+1/p-1/t5-,6+,8?,9+,10+;/m0./s1
• InChIKey: DQNKELIJSZBCBE-JSCDIZMHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• IUPAC Traditional name: sodium (4S,6R)-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-5,6-dihydro-4H-pyran-2-carboxylate
• Synonyms: 2,3-Dehydro-2-deoxy-N-acetylneuraminic Acid; N-Acetyl-2,3-dehydro-2-deoxyneuraminic Acid Sodium Salt

Database IDs

• CAS Number: 209977-53-7
• PubChem SID: 162253234
• PubChem CID: 71312795

CALCULATED PROPERTIES

• Acid pKa: 3.4996006
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -5.7101603
• LogD (pH = 7.4): -7.0726485
• Log P: -3.688152
• Molar Refractivity: 74.9478 cm^3
• Polarizability: 25.166344 Å^3
• Polar Surface Area: 159.38 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White-to-Off-White Solid
• Melting Point: >140°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A172200

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)