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

ID: ALA2062766

PubChem CID: 70696885

Max Phase: Preclinical

Molecular Formula: C15H10ClNO3S3

Molecular Weight: 383.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCN1C(=O)/C(=C/c2csc3ccc(Cl)cc23)SC1=S

Standard InChI:  InChI=1S/C15H10ClNO3S3/c16-9-1-2-11-10(6-9)8(7-22-11)5-12-14(20)17(15(21)23-12)4-3-13(18)19/h1-2,5-7H,3-4H2,(H,18,19)/b12-5-

Standard InChI Key:  GDPMGNBUYVVMDO-XGICHPGQSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   18.9514   -4.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7710   -4.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5426   -3.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7172   -3.8066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2388   -3.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4529   -3.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4481   -4.2102    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.2316   -4.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4832   -5.2555    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.4999   -2.3509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7340   -2.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0234   -3.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3725   -4.5655    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.1212   -4.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8107   -3.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2137   -3.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7917   -2.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9668   -2.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5658   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9901   -3.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5425   -1.8377    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.1810   -5.2474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1863   -3.8177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
 11 12  1  0
 12 16  1  0
  3  4  1  0
  5  6  1  0
 15 13  1  0
 13 14  1  0
 14 12  2  0
  6  7  1  0
  7  8  1  0
 15 16  2  0
  8  4  1  0
 16 17  1  0
  4  5  1  0
 17 18  2  0
  8  9  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  5 10  2  0
 18 21  1  0
  1  3  1  0
  2 22  1  0
  6 11  2  0
  2 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2062766

   3-[(5Z)-5-[(5-chloro-1-benzothiophen-3-yl)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: 383.90

Molecular Weight (Monoisotopic): 382.9511

AlogP: 4.23

#Rotatable Bonds: 4

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: 4.67

CX Basic pKa: ┄

CX LogP: 4.16

CX LogD: 1.49

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.63

Np Likeness Score: -1.95

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