3-Benzyl-5-(3,5-dichlorobenzylidene)-2-thioxothiazolidin-4-one

ID: ALA2062723

PubChem CID: 70690644

Max Phase: Preclinical

Molecular Formula: C17H11Cl2NOS2

Molecular Weight: 380.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2cc(Cl)cc(Cl)c2)SC(=S)N1Cc1ccccc1

Standard InChI:  InChI=1S/C17H11Cl2NOS2/c18-13-6-12(7-14(19)9-13)8-15-16(21)20(17(22)23-15)10-11-4-2-1-3-5-11/h1-9H,10H2/b15-8-

Standard InChI Key:  YWNOYEVDAMMRJP-NVNXTCNLSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   12.8756  -15.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4586  -15.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8655  -16.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6895  -16.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1047  -15.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6953  -15.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4667  -14.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6411  -14.2810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1626  -13.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3766  -13.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3718  -14.6847    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.1555  -14.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4071  -15.7302    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.4238  -12.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6576  -13.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9467  -13.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2286  -13.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5183  -13.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5260  -14.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2499  -15.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9573  -14.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7995  -13.4787    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.2610  -15.9422    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
  9 14  2  0
  1  7  1  0
 10 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
  8  9  1  0
 17 18  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  2  3  1  0
 20 21  2  0
 21 16  1  0
  5  6  2  0
 18 22  1  0
  9 10  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2062723

   (5Z)-3-benzyl-5-[(3,5-dichlorophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one

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: 380.32

Molecular Weight (Monoisotopic): 378.9659

AlogP: 5.39

#Rotatable Bonds: 3

Polar Surface Area: 20.31

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.90

CX LogD: 5.90

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.53

Np Likeness Score: -1.88

References

1. Robertson MJ, Hadzic G, Ambrus J, Pomè DY, Hyde E, Whiting A, Mariana A, von Kleist L, Chau N, Haucke V, Robinson PJ, McCluskey A..  (2012)  The Rhodadyns, a New Class of Small Molecule Inhibitors of Dynamin GTPase Activity.,  3  (5): [PMID:24900478] [10.1021/ml200284s]

Source

Source(1):

• Scientific Literature