2,4-Dichloro-N-(1-(2-cyanobenzyl)piperidin-4-yl)benzamide

ID: ALA4091409

PubChem CID: 137654858

Max Phase: Preclinical

Molecular Formula: C20H19Cl2N3O

Molecular Weight: 388.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccccc1CN1CCC(NC(=O)c2ccc(Cl)cc2Cl)CC1

Standard InChI:  InChI=1S/C20H19Cl2N3O/c21-16-5-6-18(19(22)11-16)20(26)24-17-7-9-25(10-8-17)13-15-4-2-1-3-14(15)12-23/h1-6,11,17H,7-10,13H2,(H,24,26)

Standard InChI Key:  PNVHAOFCDKXBDN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   20.0899  -17.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0888  -17.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7968  -18.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5065  -17.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5037  -16.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7950  -16.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7926  -15.7740    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.3808  -18.2276    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.2098  -16.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9191  -16.9911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2067  -15.7680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6252  -16.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3331  -16.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0371  -16.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0383  -15.7631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3292  -15.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6190  -15.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7460  -15.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4537  -15.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4486  -16.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1555  -16.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8642  -16.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8616  -15.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1541  -15.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1504  -14.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1472  -13.7178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  2  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 24 25  1  0
 25 26  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091409

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 388.30

Molecular Weight (Monoisotopic): 387.0905

AlogP: 4.26

#Rotatable Bonds: 4

Polar Surface Area: 56.13

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: 7.12

CX LogP: 3.86

CX LogD: 3.68

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.85

Np Likeness Score: -2.08

References

1. Jørgensen L, Al-Khawaja A, Kickinger S, Vogensen SB, Skovgaard-Petersen J, Rosenthal E, Borkar N, Löffler R, Madsen KK, Bräuner-Osborne H, Schousboe A, Ecker GF, Wellendorph P, Clausen RP..  (2017)  Structure-Activity Relationship, Pharmacological Characterization, and Molecular Modeling of Noncompetitive Inhibitors of the Betaine/γ-Aminobutyric Acid Transporter 1 (BGT1).,  60  (21): [PMID:28991462] [10.1021/acs.jmedchem.7b00924]

Source

Source(1):

• Scientific Literature