(E)-2-cyano-2-((Z)-3-ethyl-4-oxo-5-(((3-(2-(pyrrolidin-1-yl)ethyl)phenyl)amino)methylene)thiazolidin-2-ylidene)-N-(trifluoromethyl)acetamide

ID: ALA5281562

Max Phase: Preclinical

Molecular Formula: C22H24F3N5O2S

Molecular Weight: 479.53

Names and Identifiers

Canonical SMILES:  CCn1c(=O)/c(=C/Nc2cccc(CCN3CCCC3)c2)s/c1=C(\C#N)C(=O)NC(F)(F)F

Standard InChI:  InChI=1S/C22H24F3N5O2S/c1-2-30-20(32)18(33-21(30)17(13-26)19(31)28-22(23,24)25)14-27-16-7-5-6-15(12-16)8-11-29-9-3-4-10-29/h5-7,12,14,27H,2-4,8-11H2,1H3,(H,28,31)/b18-14-,21-17+

Standard InChI Key:  JINUYEMGHKIEKW-ADDAYVOGSA-N

Molfile:  

 
     RDKit          2D

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    4.4252    1.1247    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8398    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2501    1.1272    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030    0.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3404   -0.4732    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189    0.7673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9998    0.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533    1.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0903   -0.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049   -0.9586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0985   -1.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6763   -0.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4691   -0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6844   -1.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8416   -0.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4203    0.1592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2938    0.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0241    1.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6064    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2359    0.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3355    1.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0410    2.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963   -0.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9226   -1.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4357    0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2015   -0.1061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3095    1.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0485   -1.9443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6064    0.1124    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
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  8  4  1  0
  8  9  2  0
  4 10  2  0
 10 11  1  0
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 13 14  1  0
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 15 16  1  0
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 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
  7 25  1  0
 25 26  1  0
  6 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30  2  1  0
 29 31  2  0
 28 32  3  0
  2 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281562

   ---

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: 479.53

Molecular Weight (Monoisotopic): 479.1603

AlogP: 1.73

#Rotatable Bonds: 7

Polar Surface Area: 90.16

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.40

CX Basic pKa: 9.62

CX LogP: 2.33

CX LogD: 1.38

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.59

Np Likeness Score: -1.57

References

1. Kaminskyy D, Kryshchyshyn A, Lesyk R..  (2017)  5-Ene-4-thiazolidinones - An efficient tool in medicinal chemistry.,  140  [PMID:28987611] [10.1016/j.ejmech.2017.09.031]

Source

Source(1):

• Scientific Literature