4-[3-(4-Methylphenyl)-4-ethyl-5-oxo-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile

ID: ALA1086121

PubChem CID: 46889873

Max Phase: Preclinical

Molecular Formula: C20H16F3N3OS

Molecular Weight: 403.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC1C(=O)N(c2ccc(C#N)c(C(F)(F)F)c2)C(=S)N1c1ccc(C)cc1

Standard InChI:  InChI=1S/C20H16F3N3OS/c1-3-17-18(27)26(19(28)25(17)14-7-4-12(2)5-8-14)15-9-6-13(11-24)16(10-15)20(21,22)23/h4-10,17H,3H2,1-2H3

Standard InChI Key:  XAULKLGBXQJPRT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.8348   -2.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8359   -3.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211   -4.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4047   -3.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4075   -2.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229   -2.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5505   -2.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2650   -2.0862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5507   -4.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649   -3.7429    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5514   -4.9809    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7636   -3.3589    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7370   -4.2205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7297   -5.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0572   -5.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5362   -4.6218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0453   -3.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928   -5.5363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933   -3.1719    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3601   -4.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7800   -5.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6050   -5.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0111   -4.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5861   -3.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625   -3.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8361   -4.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3190   -6.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2276   -6.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  7  8  3  0
  1  7  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
  4 13  1  0
 14 18  2  0
  2  9  1  0
 17 19  2  0
 16 20  1  0
  4  5  1  0
  9 10  1  0
 20 21  2  0
  2  3  1  0
 21 22  1  0
  9 11  1  0
 22 23  2  0
  5  6  2  0
 23 24  1  0
  9 12  1  0
 24 25  2  0
 25 20  1  0
 13 14  1  0
 23 26  1  0
  6  1  1  0
 15 27  1  0
  1  2  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1086121

   4-[4-Ethyl-3-(4-methylphenyl)-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile

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: 403.43

Molecular Weight (Monoisotopic): 403.0966

AlogP: 4.80

#Rotatable Bonds: 3

Polar Surface Area: 47.34

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.99

CX Basic pKa: ┄

CX LogP: 5.54

CX LogD: 5.54

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.69

Np Likeness Score: -1.43

References

1. Jung ME, Ouk S, Yoo D, Sawyers CL, Chen C, Tran C, Wongvipat J..  (2010)  Structure-activity relationship for thiohydantoin androgen receptor antagonists for castration-resistant prostate cancer (CRPC).,  53  (7): [PMID:20218717] [10.1021/jm901488g]

Source

Source(1):

• Scientific Literature