2-{1-[2-(3-hydroxy-2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamide

• ChemBase ID: 170181
• Molecular Formular: C28H30N2O3
• Molecular Mass: 442.5494
• Monoisotopic Mass: 442.22564283
• SMILES: C(Cc1cc2c(cc1)OCC2O)N1CC(CC1)C(c1ccccc1)(c1ccccc1)C(=O)N
• Canonical SMILES: NC(=O)C(c1ccccc1)(c1ccccc1)C1CCN(C1)CCc1ccc2c(c1)C(O)CO2
• InChI: InChI=1S/C28H30N2O3/c29-27(32)28(21-7-3-1-4-8-21,22-9-5-2-6-10-22)23-14-16-30(18-23)15-13-20-11-12-26-24(17-20)25(31)19-33-26/h1-12,17,23,25,31H,13-16,18-19H2,(H2,29,32)
• InChIKey: MQEQBFMESJKUBQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{1-[2-(3-hydroxy-2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamide
• IUPAC Traditional name: 2-{1-[2-(3-hydroxy-2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamide
• Synonyms: 1-[2-(2,3-Dihydro-3-hydroxy-5-benzofuranyl)ethyl]-α,α-diphenyl-3-pyrrolidineacetamide; UK 148993; 3-Hydroxy Darifenacin(Mixture of Diastereomers)

Database IDs

• CAS Number: 1285875-62-8
• PubChem SID: 164226091
• PubChem CID: 71748849

CALCULATED PROPERTIES

• Acid pKa: 13.44359
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.1588343
• LogD (pH = 7.4): 1.0459231
• Log P: 3.621288
• Molar Refractivity: 129.5822 cm^3
• Polarizability: 50.427326 Å^3
• Polar Surface Area: 75.79 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Orange Solid
• Melting Point: 90-95°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H825190

The hydroxylated metabolite of Darifenacin (D193400).

REFERENCES

• Soudijn, W., et al.: Eur. J. Pharmacol., 1, 47 (1967)
• John, B., et al.: Xenobiotica, 22, 1339 (1967)
• Franz, P., et al.: Drug Metab. Dispos., 21, 249 (1967)