(Z)-5-(3-bromo-2-hydroxy-5-nitrobenzylidene)-2-thioxo-3-m-tolylthiazolidin-4-one

ID: ALA593310

PubChem CID: 2258834

Max Phase: Preclinical

Molecular Formula: C17H11BrN2O4S2

Molecular Weight: 451.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(N2C(=O)/C(=C/c3cc([N+](=O)[O-])cc(Br)c3O)SC2=S)c1

Standard InChI:  InChI=1S/C17H11BrN2O4S2/c1-9-3-2-4-11(5-9)19-16(22)14(26-17(19)25)7-10-6-12(20(23)24)8-13(18)15(10)21/h2-8,21H,1H3/b14-7-

Standard InChI Key:  QVRWXCIPARSBJT-AUWJEWJLSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   10.2986   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2974   -5.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0122   -5.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7287   -5.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7258   -4.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0104   -4.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4403   -5.7733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6890   -6.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5140   -6.5664    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.7753   -5.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1115   -5.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1988   -7.2235    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1180   -4.4687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4949   -5.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2041   -5.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1911   -6.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8994   -7.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6201   -6.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6280   -5.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9190   -5.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9269   -4.5739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3462   -5.4107    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.8906   -7.8774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5995   -8.2993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1707   -8.2804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0080   -3.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
 11 13  2  0
  7  8  1  0
 10 14  2  0
  1  2  2  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
 16 17  1  0
  4  5  1  0
 17 18  2  0
  2  3  1  0
 18 19  1  0
  8  9  1  0
 19 20  2  0
 20 15  1  0
  9 10  1  0
 20 21  1  0
 10 11  1  0
 19 22  1  0
 11  7  1  0
  4  7  1  0
  5  6  2  0
 23 24  2  0
 23 25  1  0
 17 23  1  0
  8 12  2  0
  6 26  1  0
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA593310

   Rhodanine, 1-2

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: 451.32

Molecular Weight (Monoisotopic): 449.9344

AlogP: 4.78

#Rotatable Bonds: 3

Polar Surface Area: 83.68

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.43

CX Basic pKa: ┄

CX LogP: 5.54

CX LogD: 3.83

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.31

Np Likeness Score: -2.07

References

1. Suree N, Yi SW, Thieu W, Marohn M, Damoiseaux R, Chan A, Jung ME, Clubb RT..  (2009)  Discovery and structure-activity relationship analysis of Staphylococcus aureus sortase A inhibitors.,  17  (20): [PMID:19781950] [10.1016/j.bmc.2009.08.067]

2.  (2017)  Arf6 inhibitors and methods of synthesis and use thereof, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data