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

ID: ALA1086119

PubChem CID: 46889871

Max Phase: Preclinical

Molecular Formula: C18H12F3N3OS

Molecular Weight: 375.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(N2CC(=O)N(c3ccc(C#N)c(C(F)(F)F)c3)C2=S)cc1

Standard InChI:  InChI=1S/C18H12F3N3OS/c1-11-2-5-13(6-3-11)23-10-16(25)24(17(23)26)14-7-4-12(9-22)15(8-14)18(19,20)21/h2-8H,10H2,1H3

Standard InChI Key:  VWFDDZGSKQSSDR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -3.3068    1.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0213    2.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7359    3.0971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0216    1.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7357    1.4405    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0222    0.2024    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2344    1.8245    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2078    0.9628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2005    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4137   -0.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654    0.5616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4255    1.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8636   -0.3530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1776    2.0115    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8893    0.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092   -0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1342   -0.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5403    0.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1153    1.2998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917    1.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3652    0.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
  1  2  2  0
  3  4  2  0
  7  8  3  0
  1  7  1  0
 14 15  1  0
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 17 13  1  0
  4 13  1  0
 14 18  2  0
  2  9  1  0
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  4  5  1  0
  9 10  1  0
 20 21  2  0
  2  3  1  0
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  9 11  1  0
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  9 12  1  0
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 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1086119

   4-[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: 375.38

Molecular Weight (Monoisotopic): 375.0653

AlogP: 4.02

#Rotatable Bonds: 2

Polar Surface Area: 47.34

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.32

CX Basic pKa: ┄

CX LogP: 4.45

CX LogD: 4.45

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: -1.64

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