5-(4-(2-(3-(4-fluorophenyl)-5-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethoxy)benzylidene)thiazolidine-2,4-dione

ID: ALA5203024

PubChem CID: 168292900

Max Phase: Preclinical

Molecular Formula: C28H19F4N3O4S

Molecular Weight: 569.54

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)/C(=C\c2ccc(OCC(=O)N3N=C(c4ccc(F)cc4)CC3c3ccc(C(F)(F)F)cc3)cc2)S1

Standard InChI:  InChI=1S/C28H19F4N3O4S/c29-20-9-5-17(6-10-20)22-14-23(18-3-7-19(8-4-18)28(30,31)32)35(34-22)25(36)15-39-21-11-1-16(2-12-21)13-24-26(37)33-27(38)40-24/h1-13,23H,14-15H2,(H,33,37,38)/b24-13+

Standard InChI Key:  KRNQTAXFNJUQTP-ZMOGYAJESA-N

Molfile:  

 
     RDKit          2D

 40 44  0  0  0  0  0  0  0  0999 V2000
   -3.3652    1.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8540    2.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5229    2.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0117    3.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8316    3.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1627    2.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739    1.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2441    4.0500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6155    0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9453    0.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9453   -0.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6525   -1.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6525   -1.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9309   -2.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189   -1.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189   -1.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9309   -3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2162   -3.6376    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6455   -3.6376    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9309   -4.0500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2808    0.5637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947    0.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185   -0.4925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849    0.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0989    0.6186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5108    1.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2969    0.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9067    1.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    2.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3403    2.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1263    2.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3858    1.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9048    1.1373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2107    1.8075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    2.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7908    3.0793    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444    2.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3346    1.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5402    1.3419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  2  2  0
  5  8  1  0
  1  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 11  2  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 21 10  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 35 34  1  0
 35 36  2  0
 37 35  1  0
 37 31  1  0
 29 38  2  0
 38 39  1  0
 39 26  2  0
 40 21  1  0
  1 40  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5203024

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 569.54

Molecular Weight (Monoisotopic): 569.1032

AlogP: 5.93

#Rotatable Bonds: 6

Polar Surface Area: 88.07

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.20

CX Basic pKa: 0.31

CX LogP: 5.31

CX LogD: 4.91

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.29

Np Likeness Score: -1.60

References

1. Upadhyay N, Tilekar K, Safuan S, Kumar AP, Schweipert M, Meyer-Almes FJ, C S R..  (2021)  Multi-target weapons: diaryl-pyrazoline thiazolidinediones simultaneously targeting VEGFR-2 and HDAC cancer hallmarks.,  12  (9.0): [PMID:34671737] [10.1039/D1MD00125F]

Source

Source(1):

• Scientific Literature