(E)-2-(1H-Benzoimidazol-2-yl)-3-(4-trifluoromethyl-phenyl)-acrylonitrile

ID: ALA118079

PubChem CID: 5886529

Max Phase: Preclinical

Molecular Formula: C17H10F3N3

Molecular Weight: 313.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1ccc(C(F)(F)F)cc1)c1nc2ccccc2[nH]1

Standard InChI:  InChI=1S/C17H10F3N3/c18-17(19,20)13-7-5-11(6-8-13)9-12(10-21)16-22-14-3-1-2-4-15(14)23-16/h1-9H,(H,22,23)/b12-9+

Standard InChI Key:  AAVUPDCCFWKWEO-FMIVXFBMSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    0.6875   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -0.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -2.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -0.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -2.1625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -2.9875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -1.3375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2958   -0.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2958   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  5 11  1  0
  6  3  2  0
  7  2  1  0
  8  3  1  0
  9  4  1  0
 10  8  3  0
 11 17  1  0
 12  5  1  0
 13  5  1  0
 14  5  1  0
 15  6  1  0
 16 18  1  0
 17 19  2  0
 18 15  2  0
 19 15  1  0
 20  7  1  0
 21  9  1  0
 22 21  2  0
 23 20  2  0
  9  7  2  0
 23 22  1  0
 16 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA118079

   (E)-2-(1H-benzimidazol-2-yl)-3-[4-(trifluoromethyl)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: 313.28

Molecular Weight (Monoisotopic): 313.0827

AlogP: 4.65

#Rotatable Bonds: 2

Polar Surface Area: 52.47

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.53

CX Basic pKa: 3.64

CX LogP: 4.57

CX LogD: 4.57

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: -1.56

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