Acetic acid 2-(2-{[2-ethyl-6-(4-nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazol-5-ylmethylene]hydrazono}-4-oxothiazolidin-5-yl)ethyl ester

ID: ALA4570275

PubChem CID: 155562485

Max Phase: Preclinical

Molecular Formula: C20H19N7O5S2

Molecular Weight: 501.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1nn2c(/C=N/N=C3/NC(=O)C(CCOC(C)=O)S3)c(-c3ccc([N+](=O)[O-])cc3)nc2s1

Standard InChI:  InChI=1S/C20H19N7O5S2/c1-3-16-25-26-14(10-21-24-19-23-18(29)15(33-19)8-9-32-11(2)28)17(22-20(26)34-16)12-4-6-13(7-5-12)27(30)31/h4-7,10,15H,3,8-9H2,1-2H3,(H,23,24,29)/b21-10+

Standard InChI Key:  LYMMCDZASHLTEN-UFFVCSGVSA-N

Molfile:  

 
     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   43.7225  -24.2622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.7042  -22.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2326  -23.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4963  -23.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.5054  -23.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2947  -24.2431    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   45.7750  -23.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2798  -22.9039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.4107  -23.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9860  -22.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1602  -22.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7581  -23.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1837  -24.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0081  -24.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4383  -22.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6271  -21.9806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.3613  -21.1981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.5501  -21.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1977  -20.2922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.3769  -20.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2180  -21.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9407  -21.6021    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   39.8175  -19.7835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.4724  -21.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7990  -21.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9331  -23.6483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.5327  -24.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5111  -22.9423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0533  -21.4237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.3798  -20.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6342  -21.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4521  -20.1322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   46.5974  -23.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.0166  -24.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0
  4  2  1  0
  2  3  2  0
  3  1  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  4  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  3  9  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 20 23  2  0
 21 24  1  0
 24 25  1  0
 26 27  2  0
 26 28  1  0
 12 26  1  0
 25 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
  7 33  1  0
 33 34  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4570275

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 501.55

Molecular Weight (Monoisotopic): 501.0889

AlogP: 2.80

#Rotatable Bonds: 8

Polar Surface Area: 153.45

Molecular Species: NEUTRAL

HBA: 12

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.34

CX Basic pKa: 1.95

CX LogP: 3.03

CX LogD: 2.69

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.21

Np Likeness Score: -1.54

References

1. Kryshchyshyn A, Kaminskyy D, Karpenko O, Gzella A, Grellier P, Lesyk R..  (2019)  Thiazolidinone/thiazole based hybrids - New class of antitrypanosomal agents.,  174  [PMID:31051403] [10.1016/j.ejmech.2019.04.052]

Source

Source(1):

• Scientific Literature