4-(2-{4-[(2R)-6,15-dibromo-13-chloro-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl]piperidin-1-yl}-2-oxoethyl)piperidine-1-carboxamide

• ChemBase ID: 128108
• Molecular Formular: C27H31Br2ClN4O2
• Molecular Mass: 638.82164
• Monoisotopic Mass: 636.05022793
• SMILES: O=C(N)N1CCC(CC(=O)N2CCC([C@@H]3c4c(Br)cc(Cl)cc4CCc4cc(Br)cnc34)CC2)CC1
• Canonical SMILES: Clc1cc(Br)c2c(c1)CCc1c([C@@H]2C2CCN(CC2)C(=O)CC2CCN(CC2)C(=O)N)ncc(c1)Br
• InChI: InChI=1S/C27H31Br2ClN4O2/c28-20-12-19-2-1-18-13-21(30)14-22(29)24(18)25(26(19)32-15-20)17-5-9-33(10-6-17)23(35)11-16-3-7-34(8-4-16)27(31)36/h12-17,25H,1-11H2,(H2,31,36)/t25-/m1/s1
• InChIKey: DHMTURDWPRKSOA-RUZDIDTESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-{4-[(2R)-6,15-dibromo-13-chloro-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl]piperidin-1-yl}-2-oxoethyl)piperidine-1-carboxamide; 4-(2-{4-[(2R)-6,15-dibromo-13-chloro-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl]piperidin-1-yl}-2-oxoethyl)piperidine-1-carboxamide
• IUPAC Traditional name: lonafarnib
• Synonyms: 4-[2-[4-[(11R)-3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl]-1-piperidinyl]-2-oxoethyl]-1-piperidinecarboxamide; Sarasar; Sch 66336; Lonafarnib

Database IDs

• CAS Number: 193275-84-2
• PubChem SID: 162222422
• PubChem CID: 148195
• CHEMBL: 298734
• Chemspider ID: 130645
• KEGG ID: D04768
• Wikipedia Title: Lonafarnib

CALCULATED PROPERTIES

• Acid pKa: 15.745956
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.7365685
• LogD (pH = 7.4): 4.7390666
• Log P: 4.7390985
• Molar Refractivity: 149.3146 cm^3
• Polarizability: 57.16543 Å^3
• Polar Surface Area: 79.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L469445

An orally bioavailable tricyclic inhibitor of farnesyl protein transferase. It inhibits Rheb farnesylation and mTOR signaling and enhances taxane and tamoxifen antitumor activity. Studies show that it induces CCAAT/enhancer-binding protein homologous prot

REFERENCES

• Liu, M. et al.: Cancer Res., 58, 4947 (1998)
• Basso, A. et al.: J. Biol. Chem., 280, 31101 (1998)
• Sun, S. et al.: J. Biol. Chem., 282, 18800 (1998)