2-(Benzimidazol-2-yl)-3-(pyridin-2-yl)acrylonitrile

ID: ALA447255

PubChem CID: 25111455

Max Phase: Preclinical

Molecular Formula: C15H10N4

Molecular Weight: 246.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1ccccn1)c1nc2ccccc2[nH]1

Standard InChI:  InChI=1S/C15H10N4/c16-10-11(9-12-5-3-4-8-17-12)15-18-13-6-1-2-7-14(13)19-15/h1-9H,(H,18,19)/b11-9+

Standard InChI Key:  UOIYATIRBXLMKX-PKNBQFBNSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   -4.8139   -7.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8151   -8.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1003   -9.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021   -7.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867   -7.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3864   -8.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5960   -8.8673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1076   -8.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -7.5227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2826   -8.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8699   -8.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8704   -7.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4625   -6.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0449   -8.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3651   -9.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1893   -9.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6024   -8.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1852   -8.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3623   -8.1972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  9  5  1  0
  4  1  1  0
  8 10  1  0
  5  6  1  0
 10 11  2  0
 10 12  1  0
  2  3  1  0
 12 13  3  0
  3  6  2  0
 11 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
M  END

Alternative Forms

1. Parent:

   

   ALA447255

   (E)-2-(1H-benzimidazol-2-yl)-3-pyridin-2-ylprop-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: 246.27

Molecular Weight (Monoisotopic): 246.0905

AlogP: 3.02

#Rotatable Bonds: 2

Polar Surface Area: 65.36

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.49

CX Basic pKa: 4.23

CX LogP: 2.71

CX LogD: 2.71

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.71

Np Likeness Score: -1.68

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