(Z)-5-(4-bromobenzylidene)-3-((phenylsulfonyl)methyl)-2-thioxothiazolidin-4-one

ID: ALA5272023

Max Phase: Preclinical

Molecular Formula: C17H12BrNO3S3

Molecular Weight: 454.39

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccc(Br)cc2)SC(=S)N1CS(=O)(=O)c1ccccc1

Standard InChI:  InChI=1S/C17H12BrNO3S3/c18-13-8-6-12(7-9-13)10-15-16(20)19(17(23)24-15)11-25(21,22)14-4-2-1-3-5-14/h1-10H,11H2/b15-10-

Standard InChI Key:  HQZSZCAEPUQWBO-GDNBJRDFSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    2.2224   -0.6916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8122    0.0242    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3973   -0.6890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6746   -0.4654    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542   -0.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122    0.3222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2601    0.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283    0.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2613    1.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6408   -1.1367    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2009    0.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7167    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3326    0.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1202    0.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7356   -0.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5631   -1.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7698   -1.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577   -0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1783   -1.6402    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.6050    0.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2161   -0.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042   -0.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1783    0.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5580    1.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7724    1.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  7  9  2  0
  5 10  2  0
  6 11  1  0
 11  2  1  0
  8 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
  2 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5272023

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 454.39

Molecular Weight (Monoisotopic): 452.9163

AlogP: 4.08

#Rotatable Bonds: 4

Polar Surface Area: 54.45

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.89

CX Basic pKa: ┄

CX LogP: 4.48

CX LogD: 4.48

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: -1.76

References

1. Kaminskyy D, Kryshchyshyn A, Lesyk R..  (2017)  5-Ene-4-thiazolidinones - An efficient tool in medicinal chemistry.,  140  [PMID:28987611] [10.1016/j.ejmech.2017.09.031]

Source

Source(1):

• Scientific Literature