2-[5-(3,5-Dichlorobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl]-acetic acid

ID: ALA2062761

PubChem CID: 22695691

Max Phase: Preclinical

Molecular Formula: C12H7Cl2NO3S2

Molecular Weight: 348.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CN1C(=O)/C(=C/c2cc(Cl)cc(Cl)c2)SC1=S

Standard InChI:  InChI=1S/C12H7Cl2NO3S2/c13-7-1-6(2-8(14)4-7)3-9-11(18)15(5-10(16)17)12(19)20-9/h1-4H,5H2,(H,16,17)/b9-3-

Standard InChI Key:  AHFDRXAXMGHASC-OQFOIZHKSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   17.6140  -23.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2052  -23.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3802  -23.0437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9021  -22.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1164  -22.6218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1116  -23.4472    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.8950  -23.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1463  -24.4920    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.1631  -21.5886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3980  -22.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6875  -22.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9699  -22.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2599  -22.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2675  -23.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9911  -23.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6981  -23.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5416  -22.2420    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.0022  -24.7039    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.1976  -24.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4390  -23.7693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5 10  2  0
  3  4  1  0
 10 11  1  0
  4  5  1  0
 11 12  2  0
  5  6  1  0
 12 13  1  0
  6  7  1  0
 13 14  2  0
  7  3  1  0
 14 15  1  0
  1  2  1  0
 15 16  2  0
 16 11  1  0
  7  8  2  0
 13 17  1  0
 15 18  1  0
  4  9  2  0
  1 19  2  0
  2  3  1  0
  1 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2062761

   2-[(5Z)-5-[(3,5-dichlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid

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: 348.23

Molecular Weight (Monoisotopic): 346.9244

AlogP: 3.28

#Rotatable Bonds: 3

Polar Surface Area: 57.61

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.37

CX Basic pKa: ┄

CX LogP: 3.65

CX LogD: 0.24

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.67

Np Likeness Score: -1.83

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