ID: ALA1628227

Max Phase: Approved

First Approval: 1969

Molecular Formula: C19H21NO

Molecular Weight: 279.38

Molecule Type: Small molecule

Representations

Synonyms (3): Doxepin | Zonalon | P-3693A
Synonyms from Alternative Forms(3):

Trade Names(2): Sinepin | Sinequan

Canonical SMILES:  CN(C)CCC=C1c2ccccc2COc2ccccc21

Standard InChI:  InChI=1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3

Standard InChI Key:  ODQWQRRAPPTVAG-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 279.38

Molecular Weight (Monoisotopic): 279.1623

AlogP: 3.96

#Rotatable Bonds: 3

Polar Surface Area: 12.47

Molecular Species: BASE

HBA: 2

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.76

CX LogP: 3.84

CX LogD: 1.51

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.84

Np Likeness Score: -0.05

References

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27. Unpublished dataset, 

28. Unpublished dataset, 

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43. Unpublished dataset, 

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Source

Source(12):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• Open TG-GATEs
• DrugMatrix
• TP-search Transporter Database
• Gene Expression Atlas Compounds
• AstraZeneca Deposited Data
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• Zimmerman Lab Biotransformation data Dec 2023