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

ID: ALA114935

PubChem CID: 5286534

Max Phase: Preclinical

Molecular Formula: C16H10N4O2

Molecular Weight: 290.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1cccc([N+](=O)[O-])c1)c1nc2ccccc2[nH]1

Standard InChI:  InChI=1S/C16H10N4O2/c17-10-12(8-11-4-3-5-13(9-11)20(21)22)16-18-14-6-1-2-7-15(14)19-16/h1-9H,(H,18,19)/b12-8+

Standard InChI Key:  BMVPYKZTAYDWTM-XYOKQWHBSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    0.6875   -1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -0.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000   -3.5875    0.0000 N   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
    1.9250   -2.1542    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
    3.9792   -2.8667    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
    3.9917   -4.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -3.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750   -1.4375    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
    3.1542   -1.4417    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
   -2.0083   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4 10  1  0
  5  1  1  0
  6  3  2  0
  7  2  1  0
  8  3  1  0
  9  5  1  0
 10 15  1  0
 11  8  3  0
 12  4  1  0
 13  4  2  0
 14  6  1  0
 15 14  2  0
 16 17  1  0
 17 20  2  0
 18  7  1  0
 19  9  1  0
 20 14  1  0
 21 18  2  0
 22 19  2  0
  9  7  2  0
 21 22  1  0
 10 16  2  0
M  CHG  2   4   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA114935

   2-(1H-Benzoimidazol-2-yl)-3-(3-nitro-phenyl)-acrylonitrile

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: 290.28

Molecular Weight (Monoisotopic): 290.0804

AlogP: 3.54

#Rotatable Bonds: 3

Polar Surface Area: 95.61

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.53

CX Basic pKa: 3.64

CX LogP: 3.63

CX LogD: 3.63

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.45

Np Likeness Score: -1.81

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