2,4-Dichloro-N-(1-(3,5-dimethoxybenzyl)piperidin-4-yl)benzamide

ID: ALA4083481

PubChem CID: 137646066

Max Phase: Preclinical

Molecular Formula: C21H24Cl2N2O3

Molecular Weight: 423.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CN2CCC(NC(=O)c3ccc(Cl)cc3Cl)CC2)cc(OC)c1

Standard InChI:  InChI=1S/C21H24Cl2N2O3/c1-27-17-9-14(10-18(12-17)28-2)13-25-7-5-16(6-8-25)24-21(26)19-4-3-15(22)11-20(19)23/h3-4,9-12,16H,5-8,13H2,1-2H3,(H,24,26)

Standard InChI Key:  ZHPMKYPXJOGYRU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   25.5255  -29.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5243  -30.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2324  -30.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9421  -30.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9392  -29.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2306  -28.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2282  -28.1144    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.8163  -30.5680    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.6454  -28.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3546  -29.3315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6423  -28.1084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0608  -28.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7686  -29.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4727  -28.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4738  -28.1035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7648  -27.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0545  -28.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1816  -27.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8893  -28.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8842  -28.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5911  -29.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2998  -28.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2972  -28.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5897  -27.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0034  -27.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5907  -30.1463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8828  -30.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0005  -26.8708    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
 21 26  1  0
 26 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4083481

   ---

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: 423.34

Molecular Weight (Monoisotopic): 422.1164

AlogP: 4.41

#Rotatable Bonds: 6

Polar Surface Area: 50.80

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: 7.69

CX LogP: 3.69

CX LogD: 3.22

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.75

Np Likeness Score: -1.46

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