4-(2,3-dichlorophenyl)-1-{4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy]butyl}piperazin-1-ium-1-olate

• ChemBase ID: 160739
• Molecular Formular: C23H27Cl2N3O3
• Molecular Mass: 464.38478
• Monoisotopic Mass: 463.1429471
• SMILES: c1ccc(c(c1N1CC[N+](CC1)(CCCCOc1ccc2c(c1)NC(=O)CC2)[O-])Cl)Cl
• Canonical SMILES: O=C1CCc2c(N1)cc(cc2)OCCCC[N+]1([O-])CCN(CC1)c1cccc(c1Cl)Cl
• InChI: InChI=1S/C23H27Cl2N3O3/c24-19-4-3-5-21(23(19)25)27-10-13-28(30,14-11-27)12-1-2-15-31-18-8-6-17-7-9-22(29)26-20(17)16-18/h3-6,8,16H,1-2,7,9-15H2,(H,26,29)
• InChIKey: ZNYNDJDSFMRJPS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2,3-dichlorophenyl)-1-{4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy]butyl}piperazin-1-ium-1-olate
• IUPAC Traditional name: 4-(2,3-dichlorophenyl)-1-{4-[(2-oxo-3,4-dihydro-1H-quinolin-7-yl)oxy]butyl}piperazin-1-ium-1-olate
• Synonyms: 7-[4-[4-(2,3-Dichlorophenyl)-1-oxido-1-piperazinyl]butoxy]-3,4-dihydro-2(1H)-quinolinone; Aripiprazole N1-Oxide

Database IDs

• CAS Number: 573691-09-5
• PubChem SID: 162254874
• PubChem CID: 10288582

CALCULATED PROPERTIES

• Acid pKa: 13.512108
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.7768295
• LogD (pH = 7.4): 3.7768676
• Log P: 3.7768686
• Molar Refractivity: 126.3813 cm^3
• Polarizability: 47.204037 Å^3
• Polar Surface Area: 68.45 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A771015

A metabolite of anti-psychotic drug, Aripiprazole (A771000).

REFERENCES

• Rowley, M., et al.: J. Med. Chem., 44, 477 ( 2001), Ozdemir, V., et al.: Curr. Opin. Invest Drugs 2002, 3, 113,,,4) Jordan, S; European Journal Pharmacol 2002, 441, 137