2-[5-(5-Chlorobenzo[b]thiophen-3-ylmethylene)-4oxo-2-thioxothiazolidin-3-yl]-acetic acid

ID: ALA2062756

PubChem CID: 70682241

Max Phase: Preclinical

Molecular Formula: C14H8ClNO3S3

Molecular Weight: 369.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CN1C(=O)/C(=C/c2csc3ccc(Cl)cc23)SC1=S

Standard InChI:  InChI=1S/C14H8ClNO3S3/c15-8-1-2-10-9(4-8)7(6-21-10)3-11-13(19)16(5-12(17)18)14(20)22-11/h1-4,6H,5H2,(H,17,18)/b11-3-

Standard InChI Key:  MLUFAPWPCYDSJX-JYOAFUTRSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -1.1914  -19.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6001  -18.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4251  -18.8922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9032  -18.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6887  -18.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6936  -19.2956    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9103  -19.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6589  -20.3404    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422  -17.4372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4072  -18.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1175  -18.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7680  -19.6507    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0197  -19.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3371  -19.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9268  -18.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3514  -17.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1770  -17.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5762  -18.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1503  -19.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6029  -16.9243    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6077  -20.3255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3664  -19.6176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 15  1  0
  4  5  1  0
  5  6  1  0
 14 12  1  0
 12 13  1  0
 13 11  2  0
  6  7  1  0
  7  3  1  0
 14 15  2  0
  1  2  1  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
 17 18  1  0
  4  9  2  0
 18 19  2  0
 19 14  1  0
  2  3  1  0
 17 20  1  0
  5 10  2  0
  1 21  2  0
  3  4  1  0
  1 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2062756

   2-[(5Z)-5-[(5-chloro-1-benzothiophen-3-yl)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: 369.88

Molecular Weight (Monoisotopic): 368.9355

AlogP: 3.84

#Rotatable Bonds: 3

Polar Surface Area: 57.61

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.11

CX Basic pKa: ┄

CX LogP: 3.92

CX LogD: 0.83

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.66

Np Likeness Score: -1.99

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