2-(5,6-Dimethylbenzimidazol-2-yl)-3-(5-nitrothiophen-2-yl)acrylonitrile

ID: ALA486866

PubChem CID: 25111346

Max Phase: Preclinical

Molecular Formula: C16H12N4O2S

Molecular Weight: 324.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2nc(/C(C#N)=C/c3ccc([N+](=O)[O-])s3)[nH]c2cc1C

Standard InChI:  InChI=1S/C16H12N4O2S/c1-9-5-13-14(6-10(9)2)19-16(18-13)11(8-17)7-12-3-4-15(23-12)20(21)22/h3-7H,1-2H3,(H,18,19)/b11-7+

Standard InChI Key:  VEJMIJMHLHRAOI-YRNVUSSQSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    4.4861    1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4849    0.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1997    0.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979    2.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9133    1.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9136    0.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7040    0.6285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1924    1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7036    1.9732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0174    1.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4301    0.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4296    2.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8375    2.7333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2551    0.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7361   -0.0817    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.5206    0.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5204    0.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7356    1.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1903   -0.3136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9438    0.0222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1043   -1.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715    2.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701    0.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  8 10  1  0
  1 22  1  0
  5  6  1  0
  2 23  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA486866

   (E)-2-(5,6-dimethyl-1H-benzimidazol-2-yl)-3-(5-nitrothiophen-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: 324.37

Molecular Weight (Monoisotopic): 324.0681

AlogP: 4.21

#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: 10.98

CX Basic pKa: 4.26

CX LogP: 4.74

CX LogD: 4.74

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.44

Np Likeness Score: -2.14

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