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

ID: ALA576895

Cas Number: 726152-87-0

PubChem CID: 2384353

Max Phase: Preclinical

Molecular Formula: C12H11N3O4S

Molecular Weight: 293.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCN1C(=O)S/C(=C\c2ccc([N+](=O)[O-])cc2)C1=O

Standard InChI:  InChI=1S/C12H11N3O4S/c13-5-6-14-11(16)10(20-12(14)17)7-8-1-3-9(4-2-8)15(18)19/h1-4,7H,5-6,13H2/b10-7-

Standard InChI Key:  DGFKDNXGDXZIMP-YFHOEESVSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   11.8557   -6.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8545   -7.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5694   -7.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2857   -7.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2828   -6.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5676   -6.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9957   -6.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7122   -6.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9586   -7.3725    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.7835   -7.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0467   -6.5979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3833   -6.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2619   -8.0526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3909   -5.2824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7628   -6.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4755   -6.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1916   -6.1947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1379   -7.8381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1373   -8.6630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4239   -7.4251    0.0000 O   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  5  1  0
 18 19  2  0
 18 20  1  0
  2 18  1  0
M  CHG  2  18   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA576895

   3-(2-Aminoethyl)-5-[(4-nitrophenyl)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: 293.30

Molecular Weight (Monoisotopic): 293.0470

AlogP: 1.59

#Rotatable Bonds: 4

Polar Surface Area: 106.54

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.14

CX LogP: 1.22

CX LogD: -0.51

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.51

Np Likeness Score: -1.81

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