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

ID: ALA4072046

PubChem CID: 137638838

Max Phase: Preclinical

Molecular Formula: C23H22Cl2N2O

Molecular Weight: 413.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1CCN(Cc2ccc3ccccc3c2)CC1)c1ccc(Cl)cc1Cl

Standard InChI:  InChI=1S/C23H22Cl2N2O/c24-19-7-8-21(22(25)14-19)23(28)26-20-9-11-27(12-10-20)15-16-5-6-17-3-1-2-4-18(17)13-16/h1-8,13-14,20H,9-12,15H2,(H,26,28)

Standard InChI Key:  DZEGOFZJGREHGY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   33.7139   -2.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7128   -3.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4249   -4.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1387   -3.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1359   -2.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4232   -2.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4207   -1.6630    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.0006   -4.1290    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.8462   -2.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5554   -2.8842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8431   -1.6570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2657   -2.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9777   -2.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6859   -2.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6870   -1.6521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.9738   -1.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2595   -1.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3989   -1.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1107   -1.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1056   -2.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8166   -2.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8153   -1.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5227   -1.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5215   -2.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2329   -2.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9459   -2.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9432   -1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2312   -1.2351    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 24  2  0
 23 22  2  0
 22 19  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4072046

   ---

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: 413.35

Molecular Weight (Monoisotopic): 412.1109

AlogP: 5.54

#Rotatable Bonds: 4

Polar Surface Area: 32.34

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.53

CX Basic pKa: 8.58

CX LogP: 5.00

CX LogD: 3.79

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -1.59

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