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

• ChemBase ID: 171378
• Molecular Formular: C31H33F3N2O6S
• Molecular Mass: 618.6637296
• Monoisotopic Mass: 618.20114245
• SMILES: c1(cccc(c1)N(S(=O)(=O)c1ccc(cn1)C(F)(F)F)O)[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)N(S(=O)(=O)c1ccc(cn1)C(F)(F)F)O)CC)O
• InChI: InChI=1S/C31H33F3N2O6S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)42-30)25(4-2)22-11-8-12-24(18-22)36(39)43(40,41)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,37,39H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1
• InChIKey: YEVFABAGWJZFRK-FYBSXPHGSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 1141510-06-6
• PubChem SID: 164227288
• PubChem CID: 71749379

CALCULATED PROPERTIES

• Acid pKa: 6.854857
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 7.116728
• LogD (pH = 7.4): 6.481892
• Log P: 7.135494
• Molar Refractivity: 156.3369 cm^3
• Polarizability: 59.930466 Å^3
• Polar Surface Area: 117.03 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H965500

A potential metabolite of Tipranavir.

REFERENCES

• Wu, J.C., Biochemistry, 30, 2022 (1991)
• Mehandru, S., et al.: Expert Opin. Invest. Drugs, 12, 1821 (1991)