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

ID: ALA4070193

PubChem CID: 137638617

Max Phase: Preclinical

Molecular Formula: C20H20Cl2N2O2

Molecular Weight: 391.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN1CCC(NC(=O)c2ccc(Cl)cc2Cl)CC1)c1ccccc1

Standard InChI:  InChI=1S/C20H20Cl2N2O2/c21-15-6-7-17(18(22)12-15)20(26)23-16-8-10-24(11-9-16)13-19(25)14-4-2-1-3-5-14/h1-7,12,16H,8-11,13H2,(H,23,26)

Standard InChI Key:  FHULZJDOOVPBCW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   11.9263   -6.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9251   -7.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6332   -8.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3428   -7.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3400   -6.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6314   -6.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6289   -5.6994    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.2171   -8.1530    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.0462   -6.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7554   -6.9165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0431   -5.6934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4616   -6.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1694   -6.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8735   -6.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8746   -5.6886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1655   -5.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4553   -5.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5823   -5.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2900   -5.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2900   -6.5058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9978   -5.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7038   -5.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4111   -5.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4115   -4.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6988   -4.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9945   -4.4668    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
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4070193

   ---

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: 391.30

Molecular Weight (Monoisotopic): 390.0902

AlogP: 4.07

#Rotatable Bonds: 5

Polar Surface Area: 49.41

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: 6.32

CX LogP: 3.51

CX LogD: 3.48

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.78

Np Likeness Score: -1.75

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