6-fluoro-2-{4-[(methylamino)methyl]phenyl}-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-one; phosphoperoxol

• ChemBase ID: 159595
• Molecular Formular: C19H19FN3O5P
• Molecular Mass: 419.3434242
• Monoisotopic Mass: 419.10463557
• SMILES: c12c3cc(cc1[nH]c(c2CCNC3=O)c1ccc(cc1)CNC)F.P(=O)(=O)OO
• Canonical SMILES: OOP(=O)=O.CNCc1ccc(cc1)c1[nH]c2c3c1CCNC(=O)c3cc(c2)F
• InChI: InChI=1S/C19H18FN3O.HO4P/c1-21-10-11-2-4-12(5-3-11)18-14-6-7-22-19(24)15-8-13(20)9-16(23-18)17(14)15;1-4-5(2)3/h2-5,8-9,21,23H,6-7,10H2,1H3,(H,22,24);1H
• InChIKey: VYBWMSCJCWNGIV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-fluoro-2-{4-[(methylamino)methyl]phenyl}-3,10-diazatricyclo[6.4.1.0^4,^1^3]trideca-1,4,6,8(13)-tetraen-9-one; phosphoperoxol
• IUPAC Traditional name: phosphoperoxol; rucaparib
• Synonyms: 8-Fluoro-1,3,4,5-tetrahydro-2-[4-[(methylamino)methyl]phenyl]-6H-pyrrolo[4,3,2-ef][2]benzazepin-6-one Phosphate; AG 014699; AG 14699

Database IDs

• CAS Number: 459868-92-9
• PubChem SID: 162253730
• PubChem CID: 71313055

CALCULATED PROPERTIES

• Acid pKa: 13.156606
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): -0.7323592
• LogD (pH = 7.4): 0.28046802
• Log P: 2.45449
• Molar Refractivity: 92.9073 cm^3
• Polarizability: 37.137505 Å^3
• Polar Surface Area: 56.92 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A425500

PARP inhibitor oncolytic.

REFERENCES

• Friedman, H., et al.: J. Clin. Oncol., 16, 3851 (1998)
• Nakajima, H., et al.: J. Pharmacol. Exp. Ther., 312, 472 (1998)
• Gajewski, T., et al.: Clin. Cancer Res., 11, 7861 (1998)