3-(2-Chloropyridin-4-yl)-3-(4-methoxyphenyl)-N-phenethylacrylamide

ID: ALA2272428

PubChem CID: 76319815

Max Phase: Preclinical

Molecular Formula: C23H21ClN2O2

Molecular Weight: 392.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C(=C/C(=O)NCCc2ccccc2)c2ccnc(Cl)c2)cc1

Standard InChI:  InChI=1S/C23H21ClN2O2/c1-28-20-9-7-18(8-10-20)21(19-12-14-25-22(24)15-19)16-23(27)26-13-11-17-5-3-2-4-6-17/h2-10,12,14-16H,11,13H2,1H3,(H,26,27)/b21-16-

Standard InChI Key:  HAFKGHJTPATLQR-PGMHBOJBSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   14.3215   -0.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3204   -0.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0340   -1.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7493   -0.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7465   -0.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0322    0.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4582    0.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1732   -0.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8849    0.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5998   -0.1229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8818    1.1115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4551    1.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1687    1.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1659    2.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4506    2.7524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7364    2.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7427    1.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3115    0.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0264   -0.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7381    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4503   -0.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1615    0.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1588    1.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4390    1.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7306    1.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0201    2.7397    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.6067   -1.3745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6060   -2.1982    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
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 10 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 16 26  1  0
  2 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2272428

   (Z)-3-(2-chloropyridin-4-yl)-3-(4-methoxyphenyl)-N-(2-phenylethyl)prop-2-enamide

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: 392.89

Molecular Weight (Monoisotopic): 392.1292

AlogP: 4.53

#Rotatable Bonds: 7

Polar Surface Area: 51.22

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.89

CX LogP: 4.45

CX LogD: 4.45

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -0.66

References

1. Xiao Y, Yang X, Li B, Yuan H, Wan S, Xu Y, Qin Z..  (2011)  Design, synthesis and antifungal/insecticidal evaluation of novel cinnamide derivatives.,  16  (11): [PMID:22027951] [10.3390/molecules16118945]

Source

Source(1):

• Scientific Literature