(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R)-6-oxo-2-(2-phenylethyl)-2-propyl-5-[(1R)-1-{3-[5-(trifluoromethyl)pyridine-2-sulfonamido]phenyl}propyl]-3,6-dihydro-2H-pyran-4-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 178671
• Molecular Formular: C37H41F3N2O11S
• Molecular Mass: 778.7884496
• Monoisotopic Mass: 778.2383158
• SMILES: c1(cccc(c1)NS(=O)(=O)c1ccc(cn1)C(F)(F)F)[C@H](C1=C(C[C@](OC1=O)(CCc1ccccc1)CCC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)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[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C37H41F3N2O11S/c1-3-16-36(17-15-21-9-6-5-7-10-21)19-26(51-35-31(45)29(43)30(44)32(52-35)33(46)47)28(34(48)53-36)25(4-2)22-11-8-12-24(18-22)42-54(49,50)27-14-13-23(20-41-27)37(38,39)40/h5-14,18,20,25,29-32,35,42-45H,3-4,15-17,19H2,1-2H3,(H,46,47)/t25-,29+,30+,31-,32+,35-,36-/m1/s1
• InChIKey: ODSCYUCOVFARRF-YFHPYYSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R)-6-oxo-2-(2-phenylethyl)-2-propyl-5-[(1R)-1-{3-[5-(trifluoromethyl)pyridine-2-sulfonamido]phenyl}propyl]-3,6-dihydro-2H-pyran-4-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R)-6-oxo-2-(2-phenylethyl)-2-propyl-5-[(1R)-1-{3-[5-(trifluoromethyl)pyridine-2-sulfonamido]phenyl}propyl]-3H-pyran-4-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (2R)-3,6-Dihydro-6-oxo-2-(2-phenylethyl)-2-propyl-5-[(1R)-1-[3-[[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]amino]phenyl]propyl]-2H-pyran-4-yl β-D-Glucopyranosiduronic Acid; Tipranavir Glucuronide; Tipranavir β-D-Glucuronide

Database IDs

• CAS Number: 947408-14-2
• PubChem SID: 164234581
• PubChem CID: 71752587

CALCULATED PROPERTIES

• Acid pKa: 3.3035207
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 2.8670492
• LogD (pH = 7.4): 0.89453167
• Log P: 5.157816
• Molar Refractivity: 186.853 cm^3
• Polarizability: 72.99237 Å^3
• Polar Surface Area: 201.81 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T444910

A metabolite of Tipranavir when coadministered with Ritonavir.

REFERENCES

• Koudriakova, T., et al.: Drug Metab. Dispos., 26, 552 (1998)
• Turner, S., et al.: J. Med. Chem., 41, 3467 (1998)
• Back, N., et al.: AIDS, 14, 101 (1998)
• Mukwaya, G., et al.: Antimicrob. Agents Chemother., 49, 4903 (1998)