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

ID: ALA4069761

PubChem CID: 47058964

Max Phase: Preclinical

Molecular Formula: C18H19Cl2N3O

Molecular Weight: 364.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1CCN(Cc2ccccn2)CC1)c1ccc(Cl)cc1Cl

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

Standard InChI Key:  HAUZEROVTILWJN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    1.5069   -2.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5058   -3.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205   -4.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9370   -3.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9342   -2.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2188   -2.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2163   -1.7122    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7910   -4.1893    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6470   -2.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3631   -2.9410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440   -1.7062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0760   -2.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7906   -2.9383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5015   -2.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5026   -1.7013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7867   -1.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0697   -1.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2171   -1.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9315   -1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9265   -2.5261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6400   -2.9385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3555   -2.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3529   -1.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6387   -1.2880    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:

   

   ALA4069761

   2,4-dichloro-N-[1-(pyridin-2-ylmethyl)piperidin-4-yl]benzamide

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: 7.61

CX LogP: 2.87

CX LogD: 2.45

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.90

Np Likeness Score: -2.27

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