5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaen-13-one

• ChemBase ID: 179470
• Molecular Formular: C13H11N3O
• Molecular Mass: 225.24594
• Monoisotopic Mass: 225.09021199
• SMILES: c12c(nccn1)cc1c(c2)C2C(=O)NCC1C2
• Canonical SMILES: O=C1NCC2CC1c1cc3nccnc3cc21
• InChI: InChI=1S/C13H11N3O/c17-13-10-3-7(6-16-13)8-4-11-12(5-9(8)10)15-2-1-14-11/h1-2,4-5,7,10H,3,6H2,(H,16,17)
• InChIKey: MQEPJJGUAJITEU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,8,14-triazatetracyclo[10.3.1.0^2,^1^1.0^4,^9]hexadeca-2,4,6,8,10-pentaen-13-one
• IUPAC Traditional name: 5,8,14-triazatetracyclo[10.3.1.0^2,^1^1.0^4,^9]hexadeca-2,4,6,8,10-pentaen-13-one
• Synonyms: 6,8,9,10-Tetrahydro-6,10-methano-7H-pyrazino[2,3-h][3]benzazepin-7-one; Varenicline Lactam

Database IDs

• CAS Number: 873302-30-8
• PubChem SID: 164235380
• PubChem CID: 46783236

CALCULATED PROPERTIES

• Acid pKa: 13.9386635
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.39307207
• LogD (pH = 7.4): 0.39311254
• Log P: 0.39311317
• Molar Refractivity: 61.4294 cm^3
• Polarizability: 25.007385 Å^3
• Polar Surface Area: 54.88 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - V098500

A metabolite of Varenicline. Metabolites M3c and M3d.

REFERENCES

• Dow, J., et al.: Drug Metab. Dispos., 22, 738 (1994)
• Toide, K., et al.: Biochem. Pharmacol., 67, 1269 (1994)
• Coe, J., et al.: J. Med. Chem., 48, 3474 (1994)
• Doll, R., et al.: Br. J. Cancer, 92, 426 (1994)