2-(benzimidazol-1-yl)-3-(4-nitrophenyl)-acrylonitrile

ID: ALA508642

PubChem CID: 25111569

Max Phase: Preclinical

Molecular Formula: C16H10N4O2

Molecular Weight: 290.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1ccc([N+](=O)[O-])cc1)n1cnc2ccccc21

Standard InChI:  InChI=1S/C16H10N4O2/c17-10-14(9-12-5-7-13(8-6-12)20(21)22)19-11-18-15-3-1-2-4-16(15)19/h1-9,11H/b14-9+

Standard InChI Key:  PIIXNERAOFGISI-NTEUORMPSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -5.4098  -23.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4109  -24.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6961  -25.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6979  -23.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9825  -23.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776  -24.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1858  -25.0046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7012  -24.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1937  -23.6600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9263  -25.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4747  -26.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1183  -25.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0233  -27.0205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588  -26.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096  -27.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1507  -28.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3419  -28.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7926  -27.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0545  -26.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799  -29.0889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717  -29.2547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6275  -29.7060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 10 11  1  0
 10 12  2  0
  2  3  1  0
 11 13  3  0
  3  6  2  0
 12 14  1  0
  1  2  2  0
 14 15  2  0
  5  4  2  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
 19 14  1  0
  9  5  1  0
  4  1  1  0
  7 10  1  0
 20 21  2  0
 20 22  1  0
 17 20  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA508642

   (E)-2-(benzimidazol-1-yl)-3-(4-nitrophenyl)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: 290.28

Molecular Weight (Monoisotopic): 290.0804

AlogP: 3.47

#Rotatable Bonds: 3

Polar Surface Area: 84.75

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.77

CX LogP: 3.25

CX LogD: 3.25

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.42

Np Likeness Score: -1.35

References

1. Saczewski F, Stencel A, Bieńczak AM, Langowska KA, Michaelis M, Werel W, Hałasa R, Reszka P, Bednarski PJ..  (2008)  Structure-activity relationships of novel heteroaryl-acrylonitriles as cytotoxic and antibacterial agents.,  43  (9): [PMID:18187237] [10.1016/j.ejmech.2007.11.017]

Source

Source(1):

• Scientific Literature