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

ID: ALA4097791

PubChem CID: 137658990

Max Phase: Preclinical

Molecular Formula: C20H19Cl2N3O

Molecular Weight: 388.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(CN2CCC(NC(=O)c3ccc(Cl)cc3Cl)CC2)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)13-15-3-1-14(12-23)2-4-15/h1-6,11,17H,7-10,13H2,(H,24,26)

Standard InChI Key:  PAECAVHKWAMWMA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   28.5507  -16.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5496  -16.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2576  -17.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9673  -16.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9645  -16.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2559  -15.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2534  -14.9031    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.8416  -17.3567    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.6706  -15.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3799  -16.1202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6676  -14.8971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0861  -15.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7939  -16.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4980  -15.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4991  -14.8923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7900  -14.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0798  -14.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2068  -14.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9145  -14.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9095  -15.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6163  -16.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3250  -15.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3224  -14.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6150  -14.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0333  -16.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7451  -16.5266    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
 22 25  1  0
 25 26  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097791

   ---

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: 7.91

CX LogP: 3.86

CX LogD: 3.23

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.85

Np Likeness Score: -2.00

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