10-hydroxyamitriptyline

ID: ALA5201360

Cas Number: 1159-82-6

PubChem CID: 155720

Max Phase: Preclinical

Molecular Formula: C20H23NO

Molecular Weight: 293.41

Names and Identifiers

Canonical SMILES:  CN(C)CCC=C1c2ccccc2CC(O)c2ccccc21

Standard InChI:  InChI=1S/C20H23NO/c1-21(2)13-7-12-17-16-9-4-3-8-15(16)14-20(22)19-11-6-5-10-18(17)19/h3-6,8-12,20,22H,7,13-14H2,1-2H3

Standard InChI Key:  GHWBJXOKAFHZAI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    0.9332    1.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660    0.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139    0.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7660    0.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9332    1.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4039    2.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4039    2.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218    2.9529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7411    1.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3540    1.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1589    0.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3789    0.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139   -0.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103   -0.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103   -1.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4347   -2.1172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4347   -2.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1589   -1.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789    0.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1589    0.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3540    1.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7411    1.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  1  1  0
  6  8  1  0
  9  5  1  0
 10  9  2  0
 11 10  1  0
 12 11  2  0
  4 12  1  0
  3 13  2  3
 13 14  1  0
 15 14  1  0
 16 15  1  0
 16 17  1  0
 16 18  1  0
 19  2  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
  1 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5201360

   10-Hydroxyamitriptyline

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 293.41

Molecular Weight (Monoisotopic): 293.1780

AlogP: 3.66

#Rotatable Bonds: 3

Polar Surface Area: 23.47

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.76

CX LogP: 3.58

CX LogD: 1.25

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.93

Np Likeness Score: 0.46

References

1. Gebauer L, Jensen O, Brockmöller J, Dücker C..  (2022)  Substrates and Inhibitors of the Organic Cation Transporter 3 and Comparison with OCT1 and OCT2.,  65  (18.0): [PMID:36067397] [10.1021/acs.jmedchem.2c01075]

Source

Source(1):

• Scientific Literature