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

ID: ALA4069676

PubChem CID: 137638595

Max Phase: Preclinical

Molecular Formula: C19H19Cl2N3O3

Molecular Weight: 408.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1CCN(Cc2ccc([N+](=O)[O-])cc2)CC1)c1ccc(Cl)cc1Cl

Standard InChI:  InChI=1S/C19H19Cl2N3O3/c20-14-3-6-17(18(21)11-14)19(25)22-15-7-9-23(10-8-15)12-13-1-4-16(5-2-13)24(26)27/h1-6,11,15H,7-10,12H2,(H,22,25)

Standard InChI Key:  FRCMFWOHRKPGFG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    9.6934  -17.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6923  -18.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4003  -18.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1100  -18.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1072  -17.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3986  -16.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3961  -15.9556    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.9843  -18.4092    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.8133  -16.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5226  -17.1727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8103  -15.9496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2287  -16.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9366  -17.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6407  -16.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6418  -15.9447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9327  -15.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2225  -15.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3495  -15.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0572  -15.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0522  -16.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7590  -17.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4677  -16.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4651  -15.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7577  -15.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1760  -17.1693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1791  -17.9829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8852  -16.7562    0.0000 O   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
 22 25  1  0
 25 26  1  0
 25 27  2  0
M  CHG  2  25   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4069676

   ---

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: 408.29

Molecular Weight (Monoisotopic): 407.0803

AlogP: 4.30

#Rotatable Bonds: 5

Polar Surface Area: 75.48

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: 7.55

CX LogP: 3.95

CX LogD: 3.57

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.59

Np Likeness Score: -1.94

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