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

• ChemBase ID: 160737
• Molecular Formular: C23H27Cl2N3O4
• Molecular Mass: 480.38418
• Monoisotopic Mass: 479.13786172
• SMILES: c1ccc(c(c1[N+]1(CC[N+](CC1)(CCCCOc1ccc2c(c1)NC(=O)CC2)[O-])[O-])Cl)Cl
• Canonical SMILES: O=C1CCc2c(N1)cc(cc2)OCCCC[N+]1([O-])CC[N+](CC1)([O-])c1cccc(c1Cl)Cl
• InChI: InChI=1S/C23H27Cl2N3O4/c24-19-4-3-5-21(23(19)25)28(31)13-11-27(30,12-14-28)10-1-2-15-32-18-8-6-17-7-9-22(29)26-20(17)16-18/h3-6,8,16H,1-2,7,9-15H2,(H,26,29)
• InChIKey: QMMBGUILKWQHOA-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}piperazine-1,4-diium-1,4-bis(olate)
• IUPAC Traditional name: 4-(2,3-dichlorophenyl)-1-{4-[(2-oxo-3,4-dihydro-1H-quinolin-7-yl)oxy]butyl}piperazine-1,4-diium-1,4-bis(olate)
• Synonyms: 7-[4-[4-(2,3-Dichlorophenyl)-1,4-dioxido-1-piperazinyl]butoxy]-3,4-dihydro-2(1H)-quinolinone; Aripiprazole N,N-Dioxide

Database IDs

• CAS Number: 573691-13-1
• PubChem SID: 162254872
• PubChem CID: 10217465

CALCULATED PROPERTIES

• Acid pKa: 13.512101
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.537629
• LogD (pH = 7.4): -0.5376007
• Log P: -0.5376
• Molar Refractivity: 137.3202 cm^3
• Polarizability: 47.75894 Å^3
• Polar Surface Area: 92.09 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A771010

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

REFERENCES

• Oshiro, Y., et al.: J. Med. Chem., 41, 658 (1998)
• Rowley, M., et al.: J. Med. Chem., 44, 477 (1998)
• McGavin, J., et al.: CNS Drugs, 16, 779 (1998)