(3R)-1-azabicyclo[2.2.2]octan-3-yl (1S,4R)-4-hydroxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

• ChemBase ID: 171305
• Molecular Formular: C23H26N2O3
• Molecular Mass: 378.46414
• Monoisotopic Mass: 378.1943427
• SMILES: c12c([C@H](CN([C@H]1c1ccccc1)C(=O)O[C@H]1CN3CCC1CC3)O)cccc2
• Canonical SMILES: O=C(N1C[C@H](O)c2c([C@@H]1c1ccccc1)cccc2)O[C@H]1CN2CCC1CC2
• InChI: InChI=1S/C23H26N2O3/c26-20-14-25(23(27)28-21-15-24-12-10-16(21)11-13-24)22(17-6-2-1-3-7-17)19-9-5-4-8-18(19)20/h1-9,16,20-22,26H,10-15H2/t20-,21-,22-/m0/s1
• InChIKey: LRNNBJBAUXSVMH-FKBYEOEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-1-azabicyclo[2.2.2]octan-3-yl (1S,4R)-4-hydroxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate
• IUPAC Traditional name: (3R)-1-azabicyclo[2.2.2]octan-3-yl (1S,4R)-4-hydroxy-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate
• Synonyms: rel-(1S,4R)-3,4-Dihydro-4-hydroxy-1-phenyl-2(1H)-isoquinolinecarboxylic Acid (3R)-1-Azabicyclo[2.2.2]oct-3-yl Ester; cis-Hydroxy Solifenacin (Mixture of Diastereomers)

Database IDs

• PubChem SID: 164227215
• PubChem CID: 71749342

CALCULATED PROPERTIES

• Acid pKa: 14.016676
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.09602847
• LogD (pH = 7.4): 1.5481704
• Log P: 3.0416095
• Molar Refractivity: 107.2657 cm^3
• Polarizability: 42.02533 Å^3
• Polar Surface Area: 53.01 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H953525

Solifenacin (S676700) metabolite.

REFERENCES

• Naito, R., et al.: J. Med. Chem., 48, 6597 (2005)
• Krauwinkel, W., et al.: Int. J. Clin. Pharmacol. Ther., 43, 227 (2005)