2-(Benzimidazol-2-yl)-3-(pyridin-4-yl)acrylonitrile

ID: ALA452337

PubChem CID: 5291138

Max Phase: Preclinical

Molecular Formula: C15H10N4

Molecular Weight: 246.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1ccncc1)c1nc2ccccc2[nH]1

Standard InChI:  InChI=1S/C15H10N4/c16-10-12(9-11-5-7-17-8-6-11)15-18-13-3-1-2-4-14(13)19-15/h1-9H,(H,18,19)/b12-9+

Standard InChI Key:  UAYSGZKWDMQVHC-FMIVXFBMSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   10.5986   -7.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5974   -8.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3122   -8.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3104   -7.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0258   -7.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0261   -8.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8165   -8.7173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3049   -8.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8161   -7.3727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1299   -8.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5426   -8.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5421   -7.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9500   -6.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3676   -8.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7776   -9.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6018   -9.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0149   -8.7604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5977   -8.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7748   -8.0472    0.0000 C   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:

   

   ALA452337

   (2E)-2-(1H-1,3-Benzodiazol-2-YL)-3-(pyridin-4-YL)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: 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: 10.53

CX Basic pKa: 4.82

CX LogP: 2.47

CX LogD: 2.47

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.71

Np Likeness Score: -1.57

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]

2. Hranjec M, Pavlović G, Marjanović M, Kralj M, Karminski-Zamola G..  (2010)  Benzimidazole derivatives related to 2,3-acrylonitriles, benzimidazo[1,2-a]quinolines and fluorenes: synthesis, antitumor evaluation in vitro and crystal structure determination.,  45  (6): [PMID:20207049] [10.1016/j.ejmech.2010.02.022]

3. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays