phosphoperoxol ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate hydrogen

• ChemBase ID: 73264
• Molecular Formular: C16H29N2O8P
• Molecular Mass: 408.383821
• Monoisotopic Mass: 408.16615253
• SMILES: [C@@H]1([C@@H]([C@H](CC(=C1)C(=O)OCC)N)NC(=O)C)OC(CC)CC.P(=O)(=O)OO
• Canonical SMILES: OOP(=O)=O.CCOC(=O)C1=C[C@H]([C@@H]([C@H](C1)N)NC(=O)C)OC(CC)CC
• InChI: InChI=1S/C16H28N2O4.HO4P/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19;1-4-5(2)3/h9,12-15H,5-8,17H2,1-4H3,(H,18,19);1H/t13-,14+,15+;/m0./s1
• InChIKey: JBTFXCKJYNSRNQ-ONAKXNSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: phosphoperoxol ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate hydrogen
• IUPAC Traditional name: oseltamivir phosphoperoxol hydrogen(.)
• Synonyms: Tamiflu; Oseltamivir phosphate

Database IDs

• CAS Number: 204255-11-8
• PubChem SID: 162038184
• PubChem CID: 56971652

CALCULATED PROPERTIES

• Acid pKa: 14.033634
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.8032612
• LogD (pH = 7.4): -0.7199175
• Log P: 1.1625985
• Molar Refractivity: 84.2034 cm^3
• Polarizability: 33.440342 Å^3
• Polar Surface Area: 90.65 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: phosphate

DETAILS

Selleck Chemicals - S2597

Research Area: Infection
Biological Activity:
Oseltamivir phosphate (Tamiflu) is a competitive neuraminidase inhibitor. The prodrug oseltamivir phosphate (Tamiflu) is itself not virally effective; however, once in the liver, it is converted by natural chemical processes, hydrolysed hepatically to its active metabolite, the free carboxylate of oseltamivir (GS4071). Oseltamivir phosphate (Tamiflu) serves as a competitive inhibitor towards sialic acid, found on the surface proteins of normal host cells. By blocking the activity of the viral neuraminidase enzyme, oseltamivir phosphate (Tamiflu) prevents new viral particles from being released by infected cells. Oseltamivir phosphate (Tamiflu) is an antiviral drug that slows the spread of influenza (flu) virus between cells in the body by stopping the virus from chemically cutting ties with its host cell. [1][2][3] References on Oseltamivir phosphate (Tamiflu)[1] http://en.wikipedia.org/wiki/Oseltamivir, , [2] PLoS Comput Biol., 2010 Sep 23, 6(9)[3] Microbes Infect., 2010 Sep, 12(10):778-83

REFERENCES

• Le L et al. PLoS Comput Biol. 2010 Sep 23; 6(9).