(E)-2-(1H-Benzoimidazol-2-yl)-3-thiophen-2-yl-acrylonitrile

ID: ALA116569

Cas Number: 104030-31-1

PubChem CID: 5334847

Max Phase: Preclinical

Molecular Formula: C14H9N3S

Molecular Weight: 251.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1cccs1)c1nc2ccccc2[nH]1

Standard InChI:  InChI=1S/C14H9N3S/c15-9-10(8-11-4-3-7-18-11)14-16-12-5-1-2-6-13(12)17-14/h1-8H,(H,16,17)/b10-8+

Standard InChI Key:  MDVSLHGZTWHJMW-CSKARUKUSA-N

Molfile:  

     RDKit          2D

 18 20  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
    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
    2.3417   -0.0125    0.0000 N   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
    3.3667   -2.7042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792   -2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -1.4792    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   -1.0417    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  1  1  0
  5  3  2  0
  6  2  1  0
  7  3  1  0
  8  4  1  0
  9  7  3  0
 10  5  1  0
 11 10  1  0
 12 11  1  0
 13 10  2  0
 14 13  1  0
 15  6  1  0
 16  8  1  0
 17 15  2  0
 18 16  2  0
  8  6  2  0
 17 18  1  0
 12 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA116569

   (2E)-2-(1H-1,3-benzodiazol-2-yl)-3-(thiophen-2-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: 251.31

Molecular Weight (Monoisotopic): 251.0517

AlogP: 3.69

#Rotatable Bonds: 2

Polar Surface Area: 52.47

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.51

CX Basic pKa: 3.62

CX LogP: 3.61

CX LogD: 3.61

Aromatic Rings: 3

Heavy Atoms: 18

QED Weighted: 0.71

Np Likeness Score: -2.24

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]

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, 

4. Li B, Cardinale SC, Butler MM, Pai R, Nuss JE, Peet NP, Bavari S, Bowlin TL..  (2011)  Time-dependent botulinum neurotoxin serotype A metalloprotease inhibitors.,  19  (24): [PMID:22082667] [10.1016/j.bmc.2011.10.062]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays