N-{3-[(1R)-1-[(6R)-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-[(1,1,2,2-2H4)propyl]-5,6-dihydro-2H-pyran-3-yl]propyl]phenyl}-5-(trifluoromethyl)pyridine-2-sulfonamide

• ChemBase ID: 178670
• Molecular Formular: C31H33F3N2O5S
• Molecular Mass: 602.6643296
• Monoisotopic Mass: 602.20622783
• SMILES: c1(cccc(c1)NS(=O)(=O)c1ccc(cn1)C(F)(F)F)[C@H](C1=C(C[C@](OC1=O)(CCc1ccccc1)CCC)O)CC
• Canonical SMILES: CCC[C@@]1(CCc2ccccc2)CC(=C(C(=O)O1)[C@@H](c1cccc(c1)NS(=O)(=O)c1ccc(cn1)C(F)(F)F)CC)O
• InChI: InChI=1S/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1
• InChIKey: SUJUHGSWHZTSEU-FYBSXPHGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{3-[(1R)-1-[(6R)-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-[(1,1,2,2-^2H₄)propyl]-5,6-dihydro-2H-pyran-3-yl]propyl]phenyl}-5-(trifluoromethyl)pyridine-2-sulfonamide
• IUPAC Traditional name: N-{3-[(1R)-1-[(6R)-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-[(1,1,2,2-^2H₄)propyl]-5H-pyran-3-yl]propyl]phenyl}-5-(trifluoromethyl)pyridine-2-sulfonamide
• Synonyms: N-[3-[(1R)-1-[(6R)-5,6-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide-d4; PNU-140690-d4; Aptivus-d4; Tipranavir-d4

Database IDs

• PubChem SID: 164234580
• PubChem CID: 57369425

CALCULATED PROPERTIES

• Acid pKa: 5.9181542
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 7.0104623
• LogD (pH = 7.4): 5.6637807
• Log P: 7.138676
• Molar Refractivity: 154.5723 cm^3
• Polarizability: 59.273716 Å^3
• Polar Surface Area: 105.59 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 65-69°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T444902

Nonpeptidic HIV protease inhibitor (NPPI). Antiviral.

REFERENCES

• Poppe, S.M., et al.: Antimicrob. Agents Chemother., 41, 1058 (1997)
• McGregor, T.R., et al.: HIV Clin. Trials, 5, 371 (1997)
• Boffito, M., et al.: J. Clin. Pharmacol., 46, 130 (1997)