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

ID: ALA577953

PubChem CID: 43145555

Max Phase: Preclinical

Molecular Formula: C12H11FN2O2S

Molecular Weight: 266.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCN1C(=O)S/C(=C\c2cccc(F)c2)C1=O

Standard InChI:  InChI=1S/C12H11FN2O2S/c13-9-3-1-2-8(6-9)7-10-11(16)15(5-4-14)12(17)18-10/h1-3,6-7H,4-5,14H2/b10-7-

Standard InChI Key:  RIZXOWYZEHZIEX-YFHOEESVSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    2.6441   -7.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6429   -8.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578   -8.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0741   -8.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0712   -7.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560   -6.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7841   -6.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5007   -7.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7470   -8.0224    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5719   -8.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8351   -7.2479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1717   -6.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0503   -8.7025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1793   -5.9323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5513   -6.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2639   -7.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9800   -6.8446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -9.3101    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  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
  3 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA577953

   (5Z)-3-(2-aminoethyl)-5-[(3-fluorophenyl)methylidene]-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: 266.30

Molecular Weight (Monoisotopic): 266.0525

AlogP: 1.82

#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: 1.42

CX LogD: -0.31

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.85

Np Likeness Score: -2.06

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