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

ID: ALA334049

PubChem CID: 11162259

Max Phase: Preclinical

Molecular Formula: C14H8N4O2S

Molecular Weight: 296.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1csc([N+](=O)[O-])c1)c1nc2ccccc2[nH]1

Standard InChI:  InChI=1S/C14H8N4O2S/c15-7-10(5-9-6-13(18(19)20)21-8-9)14-16-11-3-1-2-4-12(11)17-14/h1-6,8H,(H,16,17)/b10-5+

Standard InChI Key:  MQESBEJZCRFYQA-BJMVGYQFSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    6.2750   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6167   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -3.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3042   -4.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -4.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5875   -5.4000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.5125   -4.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3292   -4.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5125   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -4.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292   -2.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7917   -5.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0417   -4.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2500   -3.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -3.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -5.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -4.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  2  0
  3  1  2  0
  4  1  1  0
  5  2  1  0
  6  1  1  0
  7 15  1  0
  8  4  2  0
  9 10  1  0
 10  8  1  0
 11  3  1  0
 12  4  1  0
 13  6  1  0
 14 12  3  0
 15 10  2  0
 16  5  1  0
 17  5  2  0
 18 11  1  0
 19 13  1  0
 20 19  2  0
 21 18  2  0
 13 11  2  0
 21 20  1  0
  7  2  1  0
M  CHG  2   5   1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA334049

   (E)-2-(1H-benzimidazol-2-yl)-3-(5-nitrothiophen-3-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: 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: 10.53

CX Basic pKa: 3.64

CX LogP: 3.58

CX LogD: 3.58

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.45

Np Likeness Score: -2.06

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]

Source

Source(1):

• Scientific Literature