3-{2-[5-(4-dimethylaminophenyl)-3-phenyl-4,5-dihydropyrazol-1-yl]-4-oxo-4,5-dihydro-1,3-thiazol-5-ylidene}-2,3-dihydro-1H-indol-2-one

ID: ALA4171287

Max Phase: Preclinical

Molecular Formula: C28H23N5O2S

Molecular Weight: 493.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(C2CC(c3ccccc3)=NN2C2=NC(=O)/C(=C3/C(=O)Nc4ccccc43)S2)cc1

Standard InChI:  InChI=1S/C28H23N5O2S/c1-32(2)19-14-12-18(13-15-19)23-16-22(17-8-4-3-5-9-17)31-33(23)28-30-27(35)25(36-28)24-20-10-6-7-11-21(20)29-26(24)34/h3-15,23H,16H2,1-2H3,(H,29,34)/b25-24-

Standard InChI Key:  XFQIZGJQGGVATP-IZHYLOQSSA-N

Molfile:  

     RDKit          2D

 36 41  0  0  0  0  0  0  0  0999 V2000
   35.3366   -8.0337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1619   -8.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4189   -7.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0838   -7.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7493   -6.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6621   -5.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9102   -5.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2446   -6.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3351   -6.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6464   -8.7021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2040   -6.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8673   -7.4781    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   38.5350   -6.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2799   -6.2076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4544   -6.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9672   -5.5415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.3202   -7.2477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.5722   -8.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3977   -8.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   39.9848   -6.7609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.4377   -6.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0465   -7.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8309   -7.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0029   -6.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3844   -5.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6024   -6.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0862   -8.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2664   -8.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7806   -9.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1152  -10.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9406  -10.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4228   -9.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6300  -10.6962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8090  -10.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9657  -11.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  5  1  0
  4  1  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
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  9  4  1  0
  2 10  2  0
  3 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
 15 16  2  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 17  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 18 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 31 34  1  0
 34 35  1  0
 34 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4171287

   ---

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: 493.59

Molecular Weight (Monoisotopic): 493.1572

AlogP: 4.90

#Rotatable Bonds: 3

Polar Surface Area: 77.37

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.03

CX Basic pKa: 4.83

CX LogP: 4.40

CX LogD: 4.40

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.53

Np Likeness Score: -1.08

References

1. Szychowski KA, Leja ML, Kaminskyy DV, Kryshchyshyn AP, Binduga UE, Pinyazhko OR, Lesyk RB, Tobiasz J, Gmiński J..  (2017)  Anticancer properties of 4-thiazolidinone derivatives depend on peroxisome proliferator-activated receptor gamma (PPARγ).,  141  [PMID:29031063] [10.1016/j.ejmech.2017.09.071]

Source

Source(1):

• Scientific Literature