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

• ChemBase ID: 159089
• Molecular Formular: C11H17NO8
• Molecular Mass: 291.25458
• Monoisotopic Mass: 291.09541651
• SMILES: [C@H]1([C@@H]([C@@H](C=C(O1)C(=O)O)NC(=O)C)O)[C@@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@H]1OC(=C[C@H]([C@H]1O)NC(=O)C)C(=O)O)O)O
• InChI: InChI=1S/C11H17NO8/c1-4(14)12-5-2-7(11(18)19)20-10(8(5)16)9(17)6(15)3-13/h2,5-6,8-10,13,15-17H,3H2,1H3,(H,12,14)(H,18,19)/t5-,6-,8-,9-,10+/m1/s1
• InChIKey: OROCJNDGXWMTBX-MTKMREKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R)-4-acetamido-3-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• IUPAC Traditional name: (4R,5R,6S)-4-acetamido-5-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-5,6-dihydro-4H-pyran-2-carboxylic acid
• Synonyms: 4-Acetylamino-Kdn2en, iso-Neu4Ac2en; 4-Acetylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-non-2-enoic Acid

Database IDs

• CAS Number: 263155-11-9
• PubChem SID: 162253224
• PubChem CID: 40634975

CALCULATED PROPERTIES

• Acid pKa: 3.5019774
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -5.7063785
• LogD (pH = 7.4): -7.0715303
• Log P: -3.688152
• Molar Refractivity: 64.1107 cm^3
• Polarizability: 25.284155 Å^3
• Polar Surface Area: 156.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: 189-191°C

DETAILS

Toronto Research Chemicals - A168160

A potential inhibitor of virus sialidase.

REFERENCES

• Sun, X-L, et al.: Carbohydrate Research, 323, 1 (2000)