(2S,3S,4S,5R,6S)-6-({2-[(1-benzylpiperidin-4-yl)methyl]-6-methoxy-3-oxo-2,3-dihydro-1H-inden-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 166496
• Molecular Formular: C29H35NO9
• Molecular Mass: 541.5895
• Monoisotopic Mass: 541.23118171
• SMILES: c1(c(cc2c(c1)C(=O)C(C2)CC1CCN(CC1)Cc1ccccc1)OC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: COc1cc2CC(C(=O)c2cc1O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)CC1CCN(CC1)Cc1ccccc1
• InChI: InChI=1S/C29H35NO9/c1-37-21-13-18-12-19(11-16-7-9-30(10-8-16)15-17-5-3-2-4-6-17)23(31)20(18)14-22(21)38-29-26(34)24(32)25(33)27(39-29)28(35)36/h2-6,13-14,16,19,24-27,29,32-34H,7-12,15H2,1H3,(H,35,36)/t19?,24-,25-,26+,27-,29+/m0/s1
• InChIKey: GUJDLRRGLWFUSI-XDBQMMMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({2-[(1-benzylpiperidin-4-yl)methyl]-6-methoxy-3-oxo-2,3-dihydro-1H-inden-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({2-[(1-benzylpiperidin-4-yl)methyl]-6-methoxy-3-oxo-1,2-dihydroinden-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2,3-Dihydro-6-methoxy-3-oxo-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-inden-5-yl β-D-Glucopyranosiduronic Acid; 6-O-Desmethyl Donepezil Glucuronide; 6-O-Desmethyl Donepezil β-D-Glucuronide

Database IDs

• CAS Number: 220170-73-0
• PubChem SID: 162260629
• PubChem CID: 71315758

CALCULATED PROPERTIES

• Acid pKa: 2.5779707
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -0.61711115
• LogD (pH = 7.4): -0.63746685
• Log P: -0.6174081
• Molar Refractivity: 139.6442 cm^3
• Polarizability: 55.113995 Å^3
• Polar Surface Area: 145.99 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D292018

A 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)