5-(3-bromo-4-phenethoxybenzylidene)thiazolidine-2,4-dione

ID: ALA3403240

PubChem CID: 118729656

Max Phase: Preclinical

Molecular Formula: C18H14BrNO3S

Molecular Weight: 404.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)/C(=C/c2ccc(OCCc3ccccc3)c(Br)c2)S1

Standard InChI:  InChI=1S/C18H14BrNO3S/c19-14-10-13(11-16-17(21)20-18(22)24-16)6-7-15(14)23-9-8-12-4-2-1-3-5-12/h1-7,10-11H,8-9H2,(H,20,21,22)/b16-11-

Standard InChI Key:  SIFWHILFECGYHK-WJDWOHSUSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4939   -0.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7903   -1.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0919   -0.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0971    0.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8007    1.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8049    2.6864    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  -10.3906   -1.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6919   -0.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8298    0.7083    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2970    1.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0470   -0.2789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0433   -1.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2859   -2.5688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7851    2.1164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 15 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 22 23  2  0
 20 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3403240

   ---

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: 404.29

Molecular Weight (Monoisotopic): 402.9878

AlogP: 4.39

#Rotatable Bonds: 5

Polar Surface Area: 55.40

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.35

CX Basic pKa: ┄

CX LogP: 4.47

CX LogD: 3.44

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.75

Np Likeness Score: -0.93

References

1. Piao YL, Ram Song A, Cho H..  (2015)  Cell-based biological evaluations of 5-(3-bromo-4-phenethoxybenzylidene)thiazolidine-2,4-dione as promising wound healing agent.,  23  (9): [PMID:25801150] [10.1016/j.bmc.2015.03.010]

Source

Source(1):

• Scientific Literature