3-(2-aminoethyl)-5-(2-ethoxybenzylidene)thiazolidine-2,4-dione

ID: ALA569545

PubChem CID: 43328130

Max Phase: Preclinical

Molecular Formula: C14H16N2O3S

Molecular Weight: 292.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccccc1/C=C1\SC(=O)N(CCN)C1=O

Standard InChI:  InChI=1S/C14H16N2O3S/c1-2-19-11-6-4-3-5-10(11)9-12-13(17)16(8-7-15)14(18)20-12/h3-6,9H,2,7-8,15H2,1H3/b12-9-

Standard InChI Key:  AVQYNOLICLPPNI-XFXZXTDPSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -4.3095   -2.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3106   -3.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5958   -3.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8795   -3.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8823   -2.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5976   -2.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1694   -2.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4528   -2.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2065   -3.2814    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3816   -3.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1184   -2.5068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817   -2.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0968   -3.9614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7742   -1.1911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978   -2.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3104   -2.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0266   -2.1035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1643   -3.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1631   -4.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4480   -4.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  5  6  2  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
  4 18  1  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA569545

   (Z)-3-(2-aminoethyl)-5-(2-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: 292.36

Molecular Weight (Monoisotopic): 292.0882

AlogP: 2.08

#Rotatable Bonds: 5

Polar Surface Area: 72.63

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.14

CX LogP: 1.48

CX LogD: -0.25

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.84

Np Likeness Score: -1.79

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