4-(4-{[2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-N-(4-{[(2R)-4-[(2H8)morpholin-4-yl]-1-(phenylsulfanyl)butan-2-yl]amino}-3-trifluoromethanesulfonylbenzenesulfonyl)benzamide

• ChemBase ID: 158820
• Molecular Formular: C47H55ClF3N5O6S3
• Molecular Mass: 974.6127096
• Monoisotopic Mass: 973.29550985
• SMILES: C1CC(=C(CC1(C)C)CN1CCN(CC1)c1ccc(cc1)C(=O)NS(=O)(=O)c1cc(c(cc1)N[C@H](CCN1CCOCC1)CSc1ccccc1)S(=O)(=O)C(F)(F)F)c1ccc(cc1)Cl
• Canonical SMILES: Clc1ccc(cc1)C1=C(CN2CCN(CC2)c2ccc(cc2)C(=O)NS(=O)(=O)c2ccc(c(c2)S(=O)(=O)C(F)(F)F)N[C@@H](CSc2ccccc2)CCN2CCOCC2)CC(CC1)(C)C
• InChI: InChI=1S/C47H55ClF3N5O6S3/c1-46(2)20-18-42(34-8-12-37(48)13-9-34)36(31-46)32-55-22-24-56(25-23-55)39-14-10-35(11-15-39)45(57)53-65(60,61)41-16-17-43(44(30-41)64(58,59)47(49,50)51)52-38(19-21-54-26-28-62-29-27-54)33-63-40-6-4-3-5-7-40/h3-17,30,38,52H,18-29,31-33H2,1-2H3,(H,53,57)/t38-/m1/s1
• InChIKey: JLYAXFNOILIKPP-KXQOOQHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(4-{[2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-N-(4-{[(2R)-4-[(^2H₈)morpholin-4-yl]-1-(phenylsulfanyl)butan-2-yl]amino}-3-trifluoromethanesulfonylbenzenesulfonyl)benzamide
• IUPAC Traditional name: 4-(4-{[2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-N-(4-{[(2R)-4-[(^2H₈)morpholin-4-yl]-1-(phenylsulfanyl)butan-2-yl]amino}-3-trifluoromethanesulfonylbenzenesulfonyl)benzamide
• Synonyms: 4-[4-[[2-(4-Chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-N-[[4-[[(1R)-3-(4-morpholinyl)-1-[(phenylthio)methyl]propyl]amino]-3-[(trifluoromethyl)sulfonyl]phenyl]sulfonyl]benzamide-d8; ABT 263-d8

Database IDs

• PubChem SID: 162252955
• PubChem CID: 46779840

CALCULATED PROPERTIES

• Acid pKa: 4.227588
• H Acceptors: 10
• H Donor: 2
• LogD (pH = 5.5): 7.765684
• LogD (pH = 7.4): 8.10442
• Log P: 8.059313
• Molar Refractivity: 256.3622 cm^3
• Polarizability: 98.489815 Å^3
• Polar Surface Area: 128.36 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Pale Yellow Solid
• Melting Point: 102-107°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A112502

A novel inhibitor of antiapoptotic BCL-2 proteins; a new promising anticancer drug candidate.

REFERENCES

• Adams, J., et al.: Science, 281, 1322 (1998)
• Degterev, A., et al.: Nat. Cell. Biol., 3, 173 (1998)
• Kitada, S., et al.: J. Med. Chem., 46, 4259 (1998)
• Danial, N., et al.: Clin. Cancer Res., 13, 7254 (1998)