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

ID: ALA117966

Cas Number: 6448-59-5

PubChem CID: 5904441

Max Phase: Preclinical

Molecular Formula: C14H8N4O3

Molecular Weight: 280.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1ccc([N+](=O)[O-])o1)c1nc2ccccc2[nH]1

Standard InChI:  InChI=1S/C14H8N4O3/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:  LISLUXJODLGWGJ-VQHVLOKHSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    0.8000   -0.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -0.2792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6250   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8125   -2.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -1.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -2.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542    0.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7292   -3.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -2.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1833   -0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1833   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  7  1  0
  5  4  1  0
  6  1  1  0
  7  9  1  0
  8  3  2  0
  9  8  1  0
 10 15  1  0
 11  2  1  0
 12  3  1  0
 13  6  1  0
 14 12  3  0
 15  9  2  0
 16  5  1  0
 17  5  2  0
 18 11  1  0
 19 13  1  0
 20 18  2  0
 21 19  2  0
 13 11  2  0
 20 21  1  0
  4 10  2  0
M  CHG  2   5   1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA117966

   alpha-((5-Nitro-2-furanyl)methylene)-1H-benzimidazole-2-acetonitrile

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: 280.24

Molecular Weight (Monoisotopic): 280.0596

AlogP: 3.13

#Rotatable Bonds: 3

Polar Surface Area: 108.75

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.47

CX Basic pKa: 3.60

CX LogP: 2.78

CX LogD: 2.78

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.45

Np Likeness Score: -1.89

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. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays