(E)-2,4-Dichloro-N-(1-cinnamylpiperidin-4-yl)benzamide

ID: ALA4071982

PubChem CID: 137638836

Max Phase: Preclinical

Molecular Formula: C21H22Cl2N2O

Molecular Weight: 389.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1CCN(C/C=C/c2ccccc2)CC1)c1ccc(Cl)cc1Cl

Standard InChI:  InChI=1S/C21H22Cl2N2O/c22-17-8-9-19(20(23)15-17)21(26)24-18-10-13-25(14-11-18)12-4-7-16-5-2-1-3-6-16/h1-9,15,18H,10-14H2,(H,24,26)/b7-4+

Standard InChI Key:  BXIRJEUENUYXJG-QPJJXVBHSA-N

Molfile:  

     RDKit          2D

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   22.6694   -2.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6683   -3.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3763   -4.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0860   -3.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0832   -2.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3746   -2.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3721   -1.5763    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.9603   -4.0299    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.7893   -2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4986   -2.7934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7863   -1.5703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2048   -2.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9126   -2.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6167   -2.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6178   -1.5655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9087   -1.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1985   -1.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3255   -1.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0332   -1.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7409   -1.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4486   -1.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4438   -2.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1507   -2.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8594   -2.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8567   -1.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1493   -1.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  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
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 20 21  1  0
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 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:

   

   ALA4071982

   ---

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: 389.33

Molecular Weight (Monoisotopic): 388.1109

AlogP: 4.90

#Rotatable Bonds: 5

Polar Surface Area: 32.34

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: 8.05

CX LogP: 4.62

CX LogD: 3.88

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.79

Np Likeness Score: -1.41

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