(E)-2-(1H-Benzoimidazol-2-yl)-3-(5-nitro-thiophen-2-yl)-acrylonitrile

ID: ALA440896

PubChem CID: 5473285

Max Phase: Preclinical

Molecular Formula: C14H8N4O2S

Molecular Weight: 296.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1ccc([N+](=O)[O-])s1)c1nc2ccccc2[nH]1

Standard InChI:  InChI=1S/C14H8N4O2S/c15-8-9(7-10-5-6-13(21-10)18(19)20)14-16-11-3-1-2-4-12(11)17-14/h1-7H,(H,16,17)/b9-7+

Standard InChI Key:  DBRVASJJQYDOPP-VQHVLOKHSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -5.3098    1.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3109    1.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5961    0.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5979    2.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8825    1.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823    1.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0918    0.8744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6035    1.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0922    2.2190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7785    1.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657    0.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3662    2.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583    2.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5407    0.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0597    0.1642    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7248    0.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245    1.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944   -0.0678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1480    0.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3085   -0.8883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 14 15  1  0
  1  2  2  0
  5  4  2  0
  6  7  1  0
  7  8  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 14  2  0
  8  9  2  0
  9  5  1  0
  4  1  1  0
 19 20  2  0
 19 21  1  0
 16 19  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA440896

   2-(2-Benzimidazolyl)-3-(5-nitro-2-thienyl)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: 296.31

Molecular Weight (Monoisotopic): 296.0368

AlogP: 3.60

#Rotatable Bonds: 3

Polar Surface Area: 95.61

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.51

CX Basic pKa: 3.62

CX LogP: 3.71

CX LogD: 3.71

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.45

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. 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