3-(4-Amino-phenyl)-2-(5-benzyl-1H-[1,2,4]triazol-3-yl)-acrylonitrile

ID: ALA117195

PubChem CID: 5869917

Max Phase: Preclinical

Molecular Formula: C20H19N5

Molecular Weight: 329.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(/C=C(\C#N)c2n[nH]c(Cc3ccccc3)n2)cc1

Standard InChI:  InChI=1S/C20H19N5/c1-25(2)18-10-8-16(9-11-18)12-17(14-21)20-22-19(23-24-20)13-15-6-4-3-5-7-15/h3-12H,13H2,1-2H3,(H,22,23,24)/b17-12+

Standard InChI Key:  DNVANFZUADSUPK-SFQUDFHCSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.2917   -3.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -4.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1125   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7292   -3.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -4.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -3.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917   -4.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4667   -2.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167   -2.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0625   -4.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8792   -3.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542   -4.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -4.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7167   -4.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5792   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7542   -3.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8917   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667   -4.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3625   -4.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2250   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -5.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7250   -3.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  2  0
  5  2  2  0
  6  4  1  0
  7  3  2  0
  8  3  1  0
  9  8  3  0
 10 14  2  0
 11 10  1  0
 12  5  1  0
 13  7  1  0
 14 17  1  0
 15 16  2  0
 16 13  1  0
 17 13  2  0
 18 12  1  0
 19 11  1  0
 20 11  1  0
 21 18  2  0
 22 18  1  0
 23 22  2  0
 24 21  1  0
 25 23  1  0
  6  5  1  0
 15 10  1  0
 24 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA117195

   (E)-2-(5-benzyl-1H-1,2,4-triazol-3-yl)-3-[4-(dimethylamino)phenyl]prop-2-enenitrile

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: 329.41

Molecular Weight (Monoisotopic): 329.1640

AlogP: 3.53

#Rotatable Bonds: 5

Polar Surface Area: 68.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.85

CX Basic pKa: 4.51

CX LogP: 4.93

CX LogD: 4.93

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: -1.33

References

1. Saczewski F, Reszka P, Gdaniec M, Grünert R, Bednarski PJ..  (2004)  Synthesis, X-ray crystal structures, stabilities, and in vitro cytotoxic activities of new heteroarylacrylonitriles.,  47  (13): [PMID:15189040] [10.1021/jm0311036]

Source

Source(1):

• Scientific Literature