1-(benzo[b]thiophen-3-yl)-4-(4-bromophenyl)-5-methylene-1H-pyrrol-2(5H)-one

ID: ALA4549124

PubChem CID: 155549502

Max Phase: Preclinical

Molecular Formula: C19H12BrNOS

Molecular Weight: 382.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1C(c2ccc(Br)cc2)=CC(=O)N1c1csc2ccccc12

Standard InChI:  InChI=1S/C19H12BrNOS/c1-12-16(13-6-8-14(20)9-7-13)10-19(22)21(12)17-11-23-18-5-3-2-4-15(17)18/h2-11H,1H2

Standard InChI Key:  UKSAKSFAZUZYKW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   44.3415   -9.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3404  -10.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0484  -10.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7581  -10.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7553   -9.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0466   -9.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6324  -10.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8906  -10.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3433  -11.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7514  -11.8251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.5508  -11.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5307  -11.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.1592  -12.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.4614   -9.2015    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   42.4226  -12.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2835  -13.8900    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   42.8306  -13.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5372  -13.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6256  -12.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9683  -12.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2222  -12.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1374  -13.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7956  -13.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
  9 12  2  0
 11 13  2  0
  5 14  1  0
 15 19  1  0
 18 16  1  0
 16 17  1  0
 17 15  2  0
 10 15  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4549124

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 382.28

Molecular Weight (Monoisotopic): 380.9823

AlogP: 5.61

#Rotatable Bonds: 2

Polar Surface Area: 20.31

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.84

CX LogD: 4.84

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.56

Np Likeness Score: -0.56

References

1. Almohaywi B, Yu TT, Iskander G, Chan DSH, Ho KKK, Rice S, Black DS, Griffith R, Kumar N..  (2019)  Dihydropyrrolones as bacterial quorum sensing inhibitors.,  29  (9): [PMID:30857746] [10.1016/j.bmcl.2019.03.004]

Source

Source(1):

• Scientific Literature