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

ID: ALA455419

PubChem CID: 25111454

Max Phase: Preclinical

Molecular Formula: C14H8BrN3S

Molecular Weight: 330.21

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H8BrN3S/c15-13-6-9(8-19-13)5-10(7-16)14-17-11-3-1-2-4-12(11)18-14/h1-6,8H,(H,17,18)/b10-5+

Standard InChI Key:  WGYDWSQCRFHYGF-BJMVGYQFSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   10.4569   -3.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4557   -3.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1706   -4.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1688   -2.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8841   -3.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8844   -3.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6749   -4.2048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1632   -3.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6744   -2.8602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9882   -3.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4009   -4.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4004   -2.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8083   -2.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2259   -4.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7069   -4.9150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4915   -4.6598    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.4912   -3.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7065   -3.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1584   -3.3495    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  9  5  1  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  2  0
  1  2  2  0
  5  4  2  0
  6  7  1  0
  7  8  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 14  1  0
  8  9  2  0
 17 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA455419

   (E)-2-(1H-benzimidazol-2-yl)-3-(5-bromothiophen-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: 330.21

Molecular Weight (Monoisotopic): 328.9622

AlogP: 4.45

#Rotatable Bonds: 2

Polar Surface Area: 52.47

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.53

CX Basic pKa: 3.64

CX LogP: 4.41

CX LogD: 4.41

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.71

Np Likeness Score: -1.94

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