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

• ChemBase ID: 91487
• Molecular Formular: C11H16NNaO8
• Molecular Mass: 313.23641
• Monoisotopic Mass: 313.07736076
• SMILES: O1C(=C[C@H]([C@H]([C@@H]1[C@@H]([C@H](CO)O)O)NC(=O)C)O)C(=O)[O-].[Na+]
• Canonical SMILES: OC[C@@H]([C@H]([C@@H]1OC(=C[C@H]([C@H]1NC(=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-;/m1./s1
• InChIKey: DQNKELIJSZBCBE-VOMLGCLUSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R,3R,4R)-3-acetamido-4-hydroxy-2-[(1R,2S)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• IUPAC Traditional name: sodium (4R,5R,6R)-5-acetamido-4-hydroxy-6-[(1R,2S)-1,2,3-trihydroxypropyl]-5,6-dihydro-4H-pyran-2-carboxylate
• Synonyms: N-Acetyl-2,3-dehydro-2-deoxyneuraminic acid sodium salt

Database IDs

• CAS Number: 209977-53-7
• MDL Number: MFCD00269867
• PubChem SID: 162078186
• PubChem CID: 71299569

CALCULATED PROPERTIES

• Acid pKa: 3.517408
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -5.7103395
• LogD (pH = 7.4): -7.0726504
• 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

• Melting Point: 227-228°C

Safety Information

• Storage Warning: Hygroscopic

DETAILS

Apollo Scientific Ltd - OR7220T

Inhibitor of bacterial, animal and viral sialidases.