2,4-Dichloro-N-(1-(pyridin-3-ylmethyl)piperidin-4-yl)benzamide

ID: ALA4063054

PubChem CID: 137637846

Max Phase: Preclinical

Molecular Formula: C18H19Cl2N3O

Molecular Weight: 364.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1CCN(Cc2cccnc2)CC1)c1ccc(Cl)cc1Cl

Standard InChI:  InChI=1S/C18H19Cl2N3O/c19-14-3-4-16(17(20)10-14)18(24)22-15-5-8-23(9-6-15)12-13-2-1-7-21-11-13/h1-4,7,10-11,15H,5-6,8-9,12H2,(H,22,24)

Standard InChI Key:  NWKBWLRCTWSXEI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   12.5436   -2.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5424   -3.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2573   -4.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9736   -3.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9708   -2.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2554   -2.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2529   -1.7371    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.8277   -4.2140    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.6837   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3996   -2.9658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6805   -1.7311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1125   -2.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8270   -2.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5378   -2.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5389   -1.7261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8231   -1.3142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1061   -1.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2533   -1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9677   -1.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9627   -2.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6763   -2.9634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3916   -2.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3890   -1.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6749   -1.3129    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  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
M  END

Alternative Forms

1. Parent:

   

   ALA4063054

   ---

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: 364.28

Molecular Weight (Monoisotopic): 363.0905

AlogP: 3.78

#Rotatable Bonds: 4

Polar Surface Area: 45.23

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: 7.62

CX LogP: 2.79

CX LogD: 2.36

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.90

Np Likeness Score: -2.02

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