3-(2-aminoethyl)-5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methylene)thiazolidine-2,4-dione

ID: ALA568808

PubChem CID: 43328143

Max Phase: Preclinical

Molecular Formula: C14H14N2O4S

Molecular Weight: 306.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCN1C(=O)S/C(=C\c2ccc3c(c2)OCCO3)C1=O

Standard InChI:  InChI=1S/C14H14N2O4S/c15-3-4-16-13(17)12(21-14(16)18)8-9-1-2-10-11(7-9)20-6-5-19-10/h1-2,7-8H,3-6,15H2/b12-8-

Standard InChI Key:  PYMFMSPHPPOAIB-WQLSENKSSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -5.1750  -16.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1750  -17.6684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4624  -18.0771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4624  -16.4257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7498  -16.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7514  -17.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0399  -18.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263  -17.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3287  -16.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0407  -16.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6167  -16.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995  -16.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529  -17.6208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1727  -17.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4362  -16.8456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279  -16.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6515  -18.3014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203  -15.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1529  -16.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8662  -16.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5830  -16.4419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 10  5  1  0
  9 11  1  0
  1  2  1  0
 11 12  2  0
 12 13  1  0
  5  6  2  0
  1  4  1  0
  6  7  1  0
  2  3  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
  7  8  2  0
 14 17  2  0
  3  6  1  0
 16 18  2  0
  8  9  1  0
 15 19  1  0
  5  4  1  0
 19 20  1  0
  9 10  2  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA568808

   (5Z)-3-(2-aminoethyl)-5-(2,3-dihydro-1,4-benzodioxin-6-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: 306.34

Molecular Weight (Monoisotopic): 306.0674

AlogP: 1.45

#Rotatable Bonds: 3

Polar Surface Area: 81.86

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.14

CX LogP: 0.79

CX LogD: -0.94

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.85

Np Likeness Score: -1.34

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