2-(Benzimidazol-2-yl)-3-(5-methoxythiopen-2-yl)acrylonitrile

ID: ALA519890

PubChem CID: 25111347

Max Phase: Preclinical

Molecular Formula: C15H11N3OS

Molecular Weight: 281.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C(\C#N)c2nc3ccccc3[nH]2)s1

Standard InChI:  InChI=1S/C15H11N3OS/c1-19-14-7-6-11(20-14)8-10(9-16)15-17-12-4-2-3-5-13(12)18-15/h2-8H,1H3,(H,17,18)/b10-8+

Standard InChI Key:  XVUNWYWWSXGZHM-CSKARUKUSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -4.4681   -3.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4693   -3.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7544   -4.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7562   -2.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0409   -3.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0406   -3.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2501   -4.0881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618   -3.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2506   -2.7435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9368   -3.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5241   -4.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5246   -2.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1167   -1.9833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3009   -4.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7819   -4.7983    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5665   -4.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5662   -3.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7815   -3.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2341   -5.0278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -5.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  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
 16 19  1  0
  9  5  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA519890

   (E)-2-(1H-benzimidazol-2-yl)-3-(5-methoxythiophen-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: 281.34

Molecular Weight (Monoisotopic): 281.0623

AlogP: 3.70

#Rotatable Bonds: 3

Polar Surface Area: 61.70

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

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: 20

QED Weighted: 0.74

Np Likeness Score: -1.44

References

1. 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