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

ID: ALA4097124

PubChem CID: 137659917

Max Phase: Preclinical

Molecular Formula: C22H21Cl2N3O

Molecular Weight: 414.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1CCN(Cc2ccc3ccccc3n2)CC1)c1ccc(Cl)cc1Cl

Standard InChI:  InChI=1S/C22H21Cl2N3O/c23-16-6-8-19(20(24)13-16)22(28)26-17-9-11-27(12-10-17)14-18-7-5-15-3-1-2-4-21(15)25-18/h1-8,13,17H,9-12,14H2,(H,26,28)

Standard InChI Key:  AIGYYZQYCLTLQL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.6206   -6.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194   -7.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3316   -8.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -7.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0426   -6.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3298   -6.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3274   -5.7324    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9073   -8.1984    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7529   -6.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4621   -6.9537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7498   -5.7264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1724   -6.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844   -6.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5926   -6.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5937   -5.7216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8805   -5.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1661   -5.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3055   -5.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0174   -5.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0123   -6.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7233   -6.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7219   -5.3081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4294   -5.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4282   -6.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1395   -6.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8526   -6.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8498   -5.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1379   -5.3046    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:

   

   ALA4097124

   ---

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: 414.34

Molecular Weight (Monoisotopic): 413.1062

AlogP: 4.94

#Rotatable Bonds: 4

Polar Surface Area: 45.23

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: 7.93

CX LogP: 4.25

CX LogD: 3.61

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.66

Np Likeness Score: -1.74

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