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

• ChemBase ID: 175943
• Molecular Formular: C16H29N2O8P
• Molecular Mass: 408.383821
• Monoisotopic Mass: 408.16615253
• SMILES: [C@@H]1([C@@H](CC(=C[C@@H]1OC(CC)CC)C(=O)OCC)N)NC(=O)C.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+;/m1./s1
• InChIKey: JBTFXCKJYNSRNQ-DSMRVHDJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: phosphoperoxol ethyl (3S,4S,5R)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
• IUPAC Traditional name: phosphoperoxol ethyl (3S,4S,5R)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
• Synonyms: (3S,4S,5R)-4-(Acetylamino)-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic Acid Ethyl Ester Phosphate; ent-Oseltamivir Phosphate

Database IDs

• CAS Number: 1035895-89-6
• PubChem SID: 164231853
• PubChem CID: 71751352

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

DETAILS

Toronto Research Chemicals - O701010

The enatiomer of the influenza neuraminidase inhibitor prodrug Oseltamivir Phosphate (O701010).

REFERENCES

• Zutter, U. et al.: J. Org. Chem., 73, 4895 (2008)