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

ID: ALA570003

PubChem CID: 43145550

Max Phase: Preclinical

Molecular Formula: C12H11N3O4S

Molecular Weight: 293.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCN1C(=O)S/C(=C\c2cccc([N+](=O)[O-])c2)C1=O

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

Standard InChI Key:  HHESRGRVGXSQPH-YFHOEESVSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -4.5264  -11.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5276  -11.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8128  -12.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0963  -11.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0992  -11.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8146  -10.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863  -10.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6696  -11.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232  -11.9274    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983  -11.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3351  -11.1528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9985  -10.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1198  -12.6075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910   -9.8370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3812  -10.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0939  -11.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8101  -10.7495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109  -13.2198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0966  -13.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5255  -13.6321    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
  3 18  1  0
M  CHG  2  18   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA570003

   (5Z)-3-(2-aminoethyl)-5-[(3-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: -2.02

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