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

ID: ALA1085704

PubChem CID: 46889902

Max Phase: Preclinical

Molecular Formula: C21H18F3N3OS

Molecular Weight: 417.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC1(C)C(=O)N(c2ccc(C#N)c(C(F)(F)F)c2)C(=S)N1c1ccc(C)cc1

Standard InChI:  InChI=1S/C21H18F3N3OS/c1-4-20(3)18(28)26(19(29)27(20)15-8-5-13(2)6-9-15)16-10-7-14(12-25)17(11-16)21(22,23)24/h5-11H,4H2,1-3H3

Standard InChI Key:  BJTOQXDHWPSSDG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    7.2444   -7.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2432   -8.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9581   -9.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6745   -8.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6716   -7.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9563   -7.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5287   -7.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8141   -6.9612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5284   -9.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8143   -8.6179    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.5278   -9.8559    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.3156   -8.2339    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.3422   -9.0955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3495   -9.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1363  -10.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6154   -9.4968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1245   -8.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6864  -10.4113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3724   -8.0469    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1292  -10.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8458  -10.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4393   -9.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8592  -10.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6842  -10.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0903   -9.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6653   -8.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8417   -8.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9152   -9.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4111  -11.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  4  5  1  0
 15 20  1  0
  9 10  1  0
 15 21  1  0
 16 22  1  0
  2  3  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
 13 14  1  0
 25 26  1  0
  6  1  1  0
 26 27  2  0
 27 22  1  0
  1  2  2  0
 25 28  1  0
  3  4  2  0
 20 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1085704

   4-[4-Ethyl-4-methyl-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: 417.46

Molecular Weight (Monoisotopic): 417.1123

AlogP: 5.19

#Rotatable Bonds: 3

Polar Surface Area: 47.34

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.97

CX LogD: 5.97

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.64

Np Likeness Score: -1.19

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