5-(5-chloro-2-hydroxybenzylidene)-3-(3-nitrobenzyl)thiazolidine-2,4-dione

ID: ALA2011396

PubChem CID: 2284978

Max Phase: Preclinical

Molecular Formula: C17H11ClN2O5S

Molecular Weight: 390.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1S/C(=C\c2cc(Cl)ccc2O)C(=O)N1Cc1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C17H11ClN2O5S/c18-12-4-5-14(21)11(7-12)8-15-16(22)19(17(23)26-15)9-10-2-1-3-13(6-10)20(24)25/h1-8,21H,9H2/b15-8-

Standard InChI Key:  BBRNHDJYYOJNPV-NVNXTCNLSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    8.2736  -20.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2724  -21.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9872  -21.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7037  -21.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7008  -20.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9854  -19.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4137  -19.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1294  -20.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1475  -21.0697    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9377  -21.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4074  -20.6284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9073  -19.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -19.1826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2321  -20.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6608  -21.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2605  -22.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6885  -22.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5142  -22.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9100  -21.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4798  -21.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7392  -21.9711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1328  -21.2461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1703  -22.6745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9830  -19.0122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9870  -22.3152    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.2104  -22.0854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 10 26  2  0
  5  7  1  0
 11 14  1  0
  3  4  2  0
 14 15  1  0
  7  8  2  0
 15 16  2  0
  8  9  1  0
 16 17  1  0
 17 18  2  0
  4  5  1  0
 18 19  1  0
  2  3  1  0
 19 20  2  0
 20 15  1  0
  5  6  2  0
  9 10  1  0
 10 11  1  0
 21 22  2  0
 21 23  1  0
 19 21  1  0
 11 12  1  0
  6 24  1  0
 12  8  1  0
  3 25  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2011396

   (5Z)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-[(3-nitrophenyl)methyl]-1,3-thiazolidine-2,4-dione

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: 390.80

Molecular Weight (Monoisotopic): 390.0077

AlogP: 4.19

#Rotatable Bonds: 4

Polar Surface Area: 100.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.57

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 4.01

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.48

Np Likeness Score: -1.97

References

1. Brvar M, Perdih A, Hodnik V, Renko M, Anderluh G, Jerala R, Solmajer T..  (2012)  In silico discovery and biophysical evaluation of novel 5-(2-hydroxybenzylidene) rhodanine inhibitors of DNA gyrase B.,  20  (8): [PMID:22444877] [10.1016/j.bmc.2012.02.052]

2. Al-Asri J, Fazekas E, Lehoczki G, Perdih A, Görick C, Melzig MF, Gyémánt G, Wolber G, Mortier J..  (2015)  From carbohydrates to drug-like fragments: Rational development of novel α-amylase inhibitors.,  23  (20): [PMID:26395057] [10.1016/j.bmc.2015.09.007]

Source

Source(1):

• Scientific Literature