2-({1-[(2H5)benzyl]piperidin-4-yl}methyl)-6-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one

• ChemBase ID: 166495
• Molecular Formular: C23H27NO3
• Molecular Mass: 365.46538
• Monoisotopic Mass: 365.19909373
• SMILES: c1(c(cc2c(c1)C(=O)C(C2)CC1CCN(CC1)Cc1ccccc1)OC)O
• Canonical SMILES: COc1cc2CC(C(=O)c2cc1O)CC1CCN(CC1)Cc1ccccc1
• InChI: InChI=1S/C23H27NO3/c1-27-22-13-18-12-19(23(26)20(18)14-21(22)25)11-16-7-9-24(10-8-16)15-17-5-3-2-4-6-17/h2-6,13-14,16,19,25H,7-12,15H2,1H3
• InChIKey: DJRBBQJREIMIEU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({1-[(^2H₅)benzyl]piperidin-4-yl}methyl)-6-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one
• IUPAC Traditional name: 2-({1-[(^2H₅)benzyl]piperidin-4-yl}methyl)-6-hydroxy-5-methoxy-2,3-dihydroinden-1-one
• Synonyms: 1-(Benzyl-d5)-4-[(6-hydroxy-5-methoxy-1-oxo-indan-2-yl)methylpiperidine; 6-O-Desmethyl Donepezil-d5

Database IDs

• CAS Number: 1189443-74-0
• PubChem SID: 162260628
• PubChem CID: 45038883

CALCULATED PROPERTIES

• Acid pKa: 9.405273
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.091991
• LogD (pH = 7.4): 2.813271
• Log P: 3.7470021
• Molar Refractivity: 107.6324 cm^3
• Polarizability: 41.605095 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Off-White to Pale-Yellow Solid
• Melting Point: 54-56°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D292017

A labelled metabolite of Donepezil (D531750), an inhibitor of acetylcholinesterase.

REFERENCES

• De Vos, F., et al.: Nuc. Med. Biol., 27, 745 (2000)
• Okereke, C., et al.: Brit. J. Clin. Pharmacol., 58, 41 (2000)