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

• ChemBase ID: 171443
• Molecular Formular: C13H13N3O
• Molecular Mass: 227.26182
• Monoisotopic Mass: 227.10586205
• SMILES: c12c(ncc(n1)O)cc1c(c2)C2CNCC1C2
• Canonical SMILES: Oc1cnc2c(n1)cc1c(c2)C2CC1CNC2
• InChI: InChI=1S/C13H13N3O/c17-13-6-15-11-2-9-7-1-8(5-14-4-7)10(9)3-12(11)16-13/h2-3,6-8,14H,1,4-5H2,(H,16,17)
• InChIKey: GKJIHIDMYKLTHW-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-6-ol
• IUPAC Traditional name: 5,8,14-triazatetracyclo[10.3.1.0^2,^1^1.0^4,^9]hexadeca-2,4,6,8,10-pentaen-6-ol
• Synonyms: 1,6,7,8,9,10-Hexahydro-6,10-methano-2H-pyrazino[2,3-h][3]benzazepin-2-one; Hydroxy Varenicline

Database IDs

• CAS Number: 357424-21-6
• PubChem SID: 164227353
• PubChem CID: 9877932

CALCULATED PROPERTIES

• Acid pKa: 11.919109
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.8988156
• LogD (pH = 7.4): -0.96255726
• Log P: 1.2985202
• Molar Refractivity: 63.5974 cm^3
• Polarizability: 25.783472 Å^3
• Polar Surface Area: 58.04 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Acid; DMSO
• Apperance: Pale Yellow Solid
• Melting Point: 292-294°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H995600

A metabolite of Varenicline. Metabolite M3b.

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)