3-[5-(3,5-Dichloro-benzylidene)-4-oxo-2-thioxothiazolidin-3-yl]-propionic acid

ID: ALA2062771

PubChem CID: 60150579

Max Phase: Preclinical

Molecular Formula: C13H9Cl2NO3S2

Molecular Weight: 362.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCN1C(=O)/C(=C/c2cc(Cl)cc(Cl)c2)SC1=S

Standard InChI:  InChI=1S/C13H9Cl2NO3S2/c14-8-3-7(4-9(15)6-8)5-10-12(19)16(13(20)21-10)2-1-11(17)18/h3-6H,1-2H2,(H,17,18)/b10-5-

Standard InChI Key:  FHEDZVAFVVEWMU-YHYXMXQVSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   12.6388  -15.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4580  -15.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2301  -14.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4050  -14.7101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9269  -14.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1412  -14.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1364  -15.1135    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.9198  -15.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1711  -16.1584    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.1879  -13.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4227  -13.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7123  -14.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9946  -13.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2847  -14.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2923  -15.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0158  -15.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7229  -15.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5663  -13.9082    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.0269  -16.3702    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.8678  -16.1502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8731  -14.7212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0
  6 11  2  0
  2  1  1  0
 11 12  1  0
  3  4  1  0
 12 13  2  0
  5  6  1  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
  7  8  1  0
 15 16  1  0
  8  4  1  0
 16 17  2  0
 17 12  1  0
  4  5  1  0
 14 18  1  0
  8  9  2  0
 16 19  1  0
  2 20  1  0
  5 10  2  0
  2 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2062771

   3-[(5Z)-5-[(3,5-dichlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic 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: 362.26

Molecular Weight (Monoisotopic): 360.9401

AlogP: 3.67

#Rotatable Bonds: 4

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: 3.83

CX Basic pKa: ┄

CX LogP: 3.89

CX LogD: 0.64

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.65

Np Likeness Score: -1.80

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