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

ID: ALA576088

PubChem CID: 45485996

Max Phase: Preclinical

Molecular Formula: C17H20N2O2S

Molecular Weight: 316.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCN1C(=O)S/C(=C\C/C=C/c2ccccc2)C1=O

Standard InChI:  InChI=1S/C17H20N2O2S/c1-18(2)12-13-19-16(20)15(22-17(19)21)11-7-6-10-14-8-4-3-5-9-14/h3-6,8-11H,7,12-13H2,1-2H3/b10-6+,15-11-

Standard InChI Key:  KEWFTRCRWUODIK-RCTBWUFCSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -0.6742  -22.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0387  -21.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7554  -22.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018  -23.0274    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8267  -23.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0899  -22.2528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265  -21.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052  -23.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4340  -20.9370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8062  -21.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5189  -22.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2351  -21.8495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9478  -22.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2386  -21.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902  -21.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031  -22.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8191  -21.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8178  -21.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5330  -20.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2469  -21.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2411  -21.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5253  -22.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  4  5  1  0
 11 12  1  0
  5  6  1  0
 12 13  1  0
  6  7  1  0
 12 14  1  0
  7  3  1  0
  1 15  1  0
  1  2  1  0
 15 16  2  0
  5  8  2  0
 16 17  1  0
 17 18  2  0
  7  9  2  0
 18 19  1  0
  2  3  2  0
 19 20  2  0
  6 10  1  0
 20 21  1  0
  3  4  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA576088

   (5Z)-3-[2-(dimethylamino)ethyl]-5-[(E)-4-phenylbut-3-enylidene]-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: 316.43

Molecular Weight (Monoisotopic): 316.1245

AlogP: 3.23

#Rotatable Bonds: 6

Polar Surface Area: 40.62

Molecular Species: BASE

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.52

CX LogP: 3.06

CX LogD: 1.92

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: -0.88

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