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

ID: ALA4079046

PubChem CID: 137650102

Max Phase: Preclinical

Molecular Formula: C18H19Cl2N3O

Molecular Weight: 364.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1CCN(Cc2ccncc2)CC1)c1ccc(Cl)cc1Cl

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

Standard InChI Key:  FSRHDIICVIWMDM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   38.0145  -28.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0133  -29.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7214  -30.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4310  -29.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4282  -28.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7196  -28.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7172  -27.7471    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   37.3053  -30.2007    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   40.1344  -28.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8436  -28.9642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.1313  -27.7411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.5498  -28.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2576  -28.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9617  -28.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9628  -27.7362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.2537  -27.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5435  -27.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6706  -27.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3783  -27.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3732  -28.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0801  -28.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7888  -28.5531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.7861  -27.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0787  -27.3269    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:

   

   ALA4079046

   ---

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: 7.72

CX LogP: 2.79

CX LogD: 2.30

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.90

Np Likeness Score: -1.88

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