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

• ChemBase ID: 160741
• Molecular Formular: C23H27Cl2N3O3
• Molecular Mass: 464.38478
• Monoisotopic Mass: 463.1429471
• SMILES: c1ccc(c(c1[N+]1(CCN(CC1)CCCCOc1ccc2c(c1)NC(=O)CC2)[O-])Cl)Cl
• Canonical SMILES: O=C1CCc2c(N1)cc(cc2)OCCCCN1CC[N+](CC1)([O-])c1cccc(c1Cl)Cl
• InChI: InChI=1S/C23H27Cl2N3O3/c24-19-4-3-5-21(23(19)25)28(30)13-11-27(12-14-28)10-1-2-15-31-18-8-6-17-7-9-22(29)26-20(17)16-18/h3-6,8,16H,1-2,7,9-15H2,(H,26,29)
• InChIKey: FDTVYHFBHZGERN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2,3-dichlorophenyl)-4-{4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy]butyl}piperazin-1-ium-1-olate
• IUPAC Traditional name: 1-(2,3-dichlorophenyl)-4-{4-[(2-oxo-3,4-dihydro-1H-quinolin-7-yl)oxy]butyl}piperazin-1-ium-1-olate
• Synonyms: 7-[4-[4-(2,3-Dichlorophenyl)-4-oxido-1-piperazinyl]butoxy]-3,4-dihydro-2(1H)-quinolinone; Aripiprazole N4-Oxide

Database IDs

• CAS Number: 573691-11-9
• PubChem SID: 162254876
• PubChem CID: 10195368

CALCULATED PROPERTIES

• Acid pKa: 13.512107
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.75467813
• LogD (pH = 7.4): 0.039250072
• Log P: 0.0692
• Molar Refractivity: 135.2753 cm^3
• Polarizability: 47.57633 Å^3
• Polar Surface Area: 68.45 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A771020

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