2-[(E)-1-Methyl-2-(5-nitro-thiophen-2-yl)-vinyl]-1H-benzoimidazole

ID: ALA117536

PubChem CID: 11185239

Max Phase: Preclinical

Molecular Formula: C14H11N3O2S

Molecular Weight: 285.33

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H11N3O2S/c1-9(8-10-6-7-13(20-10)17(18)19)14-15-11-4-2-3-5-12(11)16-14/h2-8H,1H3,(H,15,16)/b9-8+

Standard InChI Key:  MLDRKPBYJLUXKJ-CMDGGOBGSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    0.6875   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -0.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6875   -3.0667    0.0000 N   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
    3.2292   -2.8292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -1.7542    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
   -0.5833   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -1.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6000   -3.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417   -2.7292    0.0000 O   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
   -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   -1.8667    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  6  1  0
  3  1  2  0
  4  2  1  0
  5  1  1  0
  6  8  1  0
  7  1  1  0
  8  9  1  0
  9  7  2  0
 10 13  1  0
 11  3  1  0
 12  5  1  0
 13  8  2  0
 14  4  1  0
 15  4  2  0
 16  7  1  0
 17 11  1  0
 18 12  1  0
 19 18  2  0
 20 17  2  0
 12 11  2  0
 20 19  1  0
  2 10  2  0
M  CHG  2   4   1  14  -1
M  END

Alternative Forms

1. Parent:

   

   ALA117536

   2-[(E)-1-(5-nitrothiophen-2-yl)prop-1-en-2-yl]-1H-benzimidazole

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: 285.33

Molecular Weight (Monoisotopic): 285.0572

AlogP: 4.09

#Rotatable Bonds: 3

Polar Surface Area: 71.82

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.49

CX Basic pKa: 5.20

CX LogP: 4.30

CX LogD: 4.29

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.58

Np Likeness Score: -1.65

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