N-methyl-N-{3-[(2E)-9-oxatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl}acetamide

• ChemBase ID: 159221
• Molecular Formular: C20H21NO2
• Molecular Mass: 307.38624
• Monoisotopic Mass: 307.15722892
• SMILES: O1Cc2c(/C(=C\CCN(C)C(=O)C)/c3c1cccc3)cccc2
• Canonical SMILES: CN(C(=O)C)CC/C=C\1/c2ccccc2OCc2c1cccc2
• InChI: InChI=1S/C20H21NO2/c1-15(22)21(2)13-7-11-18-17-9-4-3-8-16(17)14-23-20-12-6-5-10-19(18)20/h3-6,8-12H,7,13-14H2,1-2H3/b18-11+
• InChIKey: BFOHVOUMOVZBKO-WOJGMQOQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-methyl-N-{3-[(2E)-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl}acetamide
• IUPAC Traditional name: N-methyl-N-{3-[(2E)-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl}acetamide
• Synonyms: N-[(3E)-3-Dibenz[b,e]oxepin-11(6H)-ylidenepropyl]-N-methylacetamide; (E)-N-Acetyl-N-desmethyl Doxepin

Database IDs

• CAS Number: 250331-54-5
• PubChem SID: 162253356
• PubChem CID: 59023614

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.0668678
• LogD (pH = 7.4): 3.0668683
• Log P: 3.0668683
• Molar Refractivity: 102.516 cm^3
• Polarizability: 35.648727 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A173545

Doxepin (D550000) metabolite.

REFERENCES

• Moody, J., et al.: Drug Metab. Disposition, 27, 1157 (1999)