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

• ChemBase ID: 179623
• Molecular Formular: C11H18N2O7
• Molecular Mass: 290.26982
• Monoisotopic Mass: 290.11140093
• SMILES: C1=C(O[C@H]([C@@H]([C@H]1N)NC(=O)C)[C@@H]([C@@H](CO)O)O)C(=O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1OC(=C[C@@H]([C@H]1NC(=O)C)N)C(=O)O)O)O
• InChI: InChI=1S/C11H18N2O7/c1-4(15)13-8-5(12)2-7(11(18)19)20-10(8)9(17)6(16)3-14/h2,5-6,8-10,14,16-17H,3,12H2,1H3,(H,13,15)(H,18,19)/t5-,6+,8+,9+,10+/m0/s1
• InChIKey: NKENBBIXEGPQLS-UFGQHTETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S)-4-amino-3-acetamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• IUPAC Traditional name: (4S,5R,6R)-4-amino-5-acetamido-6-[(1R,2R)-1,2,3-trihydroxypropyl]-5,6-dihydro-4H-pyran-2-carboxylic acid
• Synonyms: 5-(Acetylamino)-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic Acid; Zanamivir Amine

Database IDs

• CAS Number: 130525-62-1
• PubChem SID: 164235533
• PubChem CID: 445533

CALCULATED PROPERTIES

• Acid pKa: 3.3003387
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -6.059817
• LogD (pH = 7.4): -6.09289
• Log P: -6.0592656
• Molar Refractivity: 65.7682 cm^3
• Polarizability: 26.099392 Å^3
• Polar Surface Area: 162.34 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - Z148005

A synthetic precursor of Zanamivir.

REFERENCES

• Gonzalez-Diaz, H., et al.: Bioorg. Med. Chem. Lett., 15, 1651 (2005)
• Bergmann, R., et al.: J. Med. Chem., 50, 2708 (2005)
• Lue, W., et al.: Eur. J. Med. Chem., 43, 569 (2005)