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

ID: ALA4077256

PubChem CID: 137649763

Max Phase: Preclinical

Molecular Formula: C20H22Cl2N2O2

Molecular Weight: 393.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(CN2CCC(NC(=O)c3ccc(Cl)cc3Cl)CC2)c1

Standard InChI:  InChI=1S/C20H22Cl2N2O2/c1-26-17-4-2-3-14(11-17)13-24-9-7-16(8-10-24)23-20(25)18-6-5-15(21)12-19(18)22/h2-6,11-12,16H,7-10,13H2,1H3,(H,23,25)

Standard InChI Key:  QNXVXZVRMUWQDO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   24.8899  -25.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8888  -26.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5968  -26.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3065  -26.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3036  -25.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5950  -25.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5926  -24.2967    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.1807  -26.7503    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.0098  -25.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7190  -25.5138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0067  -24.2907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4252  -25.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1331  -25.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8371  -25.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8383  -24.2859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1292  -23.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4189  -24.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5460  -23.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2537  -24.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2486  -25.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9555  -25.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6642  -25.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6616  -24.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9541  -23.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3678  -23.8703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0770  -24.2764    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
 23 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4077256

   ---

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: 393.31

Molecular Weight (Monoisotopic): 392.1058

AlogP: 4.40

#Rotatable Bonds: 5

Polar Surface Area: 41.57

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: 8.05

CX LogP: 3.85

CX LogD: 3.12

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.82

Np Likeness Score: -1.79

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