3-(2-aminoethyl)-5-(naphthalen-1-ylmethylene)thiazolidine-2,4-dione

ID: ALA577100

PubChem CID: 43328137

Max Phase: Preclinical

Molecular Formula: C16H14N2O2S

Molecular Weight: 298.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCN1C(=O)S/C(=C\c2cccc3ccccc23)C1=O

Standard InChI:  InChI=1S/C16H14N2O2S/c17-8-9-18-15(19)14(21-16(18)20)10-12-6-3-5-11-4-1-2-7-13(11)12/h1-7,10H,8-9,17H2/b14-10-

Standard InChI Key:  FCSZHKPGQJRTSN-UVTDQMKNSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   13.7608  -12.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4756  -12.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1922  -12.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1893  -11.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9022  -10.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6190  -11.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8654  -11.9782    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.6903  -11.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9536  -11.2035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2901  -10.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1689  -12.6583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2976   -9.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6699  -10.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3826  -11.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0989  -10.8002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7620  -11.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4728  -10.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4707   -9.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7587   -9.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0471   -9.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0526  -10.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10  6  1  0
  1  2  1  0
  8 11  2  0
  4  5  1  0
 10 12  2  0
 16  1  2  0
  9 13  1  0
  5  6  2  0
 13 14  1  0
  6  7  1  0
 14 15  1  0
  2  3  2  0
 16 17  1  0
  3  4  1  0
 17 18  1  0
  4 17  2  0
 18 19  2  0
  7  8  1  0
 19 20  1  0
  8  9  1  0
 20 21  2  0
 21 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA577100

   (5Z)-3-(2-aminoethyl)-5-(naphthalen-1-ylmethylidene)-1,3-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: 298.37

Molecular Weight (Monoisotopic): 298.0776

AlogP: 2.83

#Rotatable Bonds: 3

Polar Surface Area: 63.40

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.14

CX LogP: 2.27

CX LogD: 0.54

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.89

Np Likeness Score: -1.48

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