(3R,4R)-4-(4-amino-5-chloro-2-methoxybenzamido)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-1-ium-1-olate

• ChemBase ID: 164787
• Molecular Formular: C23H29ClFN3O5
• Molecular Mass: 481.9448632
• Monoisotopic Mass: 481.17797694
• SMILES: c1cc(ccc1OCCC[N+]1(C[C@H]([C@@H](CC1)NC(=O)c1c(cc(c(c1)Cl)N)OC)OC)[O-])F
• Canonical SMILES: CO[C@@H]1C[N+]([O-])(CCCOc2ccc(cc2)F)CC[C@H]1NC(=O)c1cc(Cl)c(cc1OC)N
• InChI: InChI=1S/C23H29ClFN3O5/c1-31-21-13-19(26)18(24)12-17(21)23(29)27-20-8-10-28(30,14-22(20)32-2)9-3-11-33-16-6-4-15(25)5-7-16/h4-7,12-13,20,22H,3,8-11,14,26H2,1-2H3,(H,27,29)/t20-,22-,28?/m1/s1
• InChIKey: CUZUZCKCMMWXEA-UJFFOEJGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-4-(4-amino-5-chloro-2-methoxybenzamido)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-1-ium-1-olate
• IUPAC Traditional name: (3R,4R)-4-(4-amino-5-chloro-2-methoxybenzamido)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-1-ium-1-olate
• Synonyms: rel-4-Amino-5-chloro-N-[(3R,4S)-1-[3-(4-fluorophenoxy)propyl]-3-methoxy-1-oxido-4-piperidinyl]-2-methoxybenzamide; (3α,4α)-(+/-)-4-Amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide N-Oxide; Cisapride N-Oxide

Database IDs

• CAS Number: 86718-75-4
• PubChem SID: 162258922
• PubChem CID: 71314875

CALCULATED PROPERTIES

• Acid pKa: 14.575129
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.3669049
• LogD (pH = 7.4): 1.3669827
• Log P: 1.3669837
• Molar Refractivity: 124.9798 cm^3
• Polarizability: 46.951912 Å^3
• Polar Surface Area: 109.69 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C496410

A metabolite of Cisapride; a biotransformation produced by human cytochrome P 450 enzymes.

REFERENCES

• Wiseman, L., et al.: Drugs, 47, 116 (1994)
• Clarke, S., et al.: Xenobiotica, 28, 1167 (1994)
• Bohets, H., et al.: Br. J. Pharmacol., 129, 1655 (1994)
• Desta, Z., et al.: Drug Metab. Disp., 28, 789 (1994)