(2E)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-ol

• ChemBase ID: 170419
• Molecular Formular: C19H21NO2
• Molecular Mass: 295.37554
• Monoisotopic Mass: 295.15722892
• SMILES: O1Cc2c(/C(=C\CCN(C)C)/c3c1ccc(c3)O)cccc2
• Canonical SMILES: CN(CC/C=C\1/c2cc(O)ccc2OCc2c1cccc2)C
• InChI: InChI=1S/C19H21NO2/c1-20(2)11-5-8-17-16-7-4-3-6-14(16)13-22-19-10-9-15(21)12-18(17)19/h3-4,6-10,12,21H,5,11,13H2,1-2H3/b17-8+
• InChIKey: GRQPGTWGEQWMMM-CAOOACKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-ol
• IUPAC Traditional name: (2E)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-ol
• Synonyms: (11E)-11-[3-(Dimethylamino)propylidene]-6,11-dihydrodibenz[b,e]oxepin-2-ol; (E)-2-Hydroxy Doxepin

Database IDs

• CAS Number: 131523-90-5
• PubChem SID: 164226329
• PubChem CID: 59023617

CALCULATED PROPERTIES

• Acid pKa: 10.074889
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.106770426
• LogD (pH = 7.4): 1.2154865
• Log P: 2.9351845
• Molar Refractivity: 100.2257 cm^3
• Polarizability: 34.738605 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H941785

A metabolite of Doxepin (D550000).

REFERENCES

• Pinder, R., et al.: Drugs, 13, 161 (1977)
• Ghabrial, H., et al.: Drug Metab. Dispos., 19, 596 (1977)
• Midha, K., et al.: Eur. J. Clin. Pharmacol., 42, 539 (1977)