3-(2-(dimethylamino)ethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

ID: ALA577105

PubChem CID: 45485994

Max Phase: Preclinical

Molecular Formula: C16H20N2O3S

Molecular Weight: 320.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc(/C=C2\SC(=O)N(CCN(C)C)C2=O)cc1

Standard InChI:  InChI=1S/C16H20N2O3S/c1-4-21-13-7-5-12(6-8-13)11-14-15(19)18(16(20)22-14)10-9-17(2)3/h5-8,11H,4,9-10H2,1-3H3/b14-11-

Standard InChI Key:  PUJLWVRCHNDSJW-KAMYIIQDSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    5.3611  -16.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3599  -17.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0747  -17.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7912  -17.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7883  -16.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0729  -16.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5012  -16.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2179  -16.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4643  -17.3441    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2892  -17.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5524  -16.5695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8890  -16.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7677  -18.0242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8965  -15.2537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2687  -16.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9814  -16.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6976  -16.1662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6451  -17.8059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9310  -17.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2162  -17.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4103  -16.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7011  -15.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  6  1  1  0
 10 13  2  0
  1  2  2  0
 12 14  2  0
  5  7  1  0
 11 15  1  0
  3  4  2  0
 15 16  1  0
  7  8  2  0
 16 17  1  0
  8  9  1  0
  2 18  1  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  2  3  1  0
 17 21  1  0
  5  6  2  0
 17 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA577105

   (Z)-3-(2-(dimethylamino)ethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

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: 320.41

Molecular Weight (Monoisotopic): 320.1195

AlogP: 2.68

#Rotatable Bonds: 6

Polar Surface Area: 49.85

Molecular Species: BASE

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.52

CX LogP: 2.29

CX LogD: 1.14

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.75

Np Likeness Score: -1.78

References

1. Li Q, Al-Ayoubi A, Guo T, Zheng H, Sarkar A, Nguyen T, Eblen ST, Grant S, Kellogg GE, Zhang S..  (2009)  Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: development of potential substrate-specific ERK1/2 inhibitors.,  19  (21): [PMID:19796943] [10.1016/j.bmcl.2009.09.057]

Source

Source(1):

• Scientific Literature