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

ID: ALA1086120

PubChem CID: 46889872

Max Phase: Preclinical

Molecular Formula: C19H14F3N3OS

Molecular Weight: 389.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(N2C(=S)N(c3ccc(C#N)c(C(F)(F)F)c3)C(=O)C2C)cc1

Standard InChI:  InChI=1S/C19H14F3N3OS/c1-11-3-6-14(7-4-11)24-12(2)17(26)25(18(24)27)15-8-5-13(10-23)16(9-15)19(20,21)22/h3-9,12H,1-2H3

Standard InChI Key:  PMASOZJHVUSLNM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.5861    2.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5849    1.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2997    1.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0162    1.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0133    2.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2979    2.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8704    2.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1558    3.2513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8701    1.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1560    1.5946    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8695    0.3566    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6572    1.9786    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.6838    1.1170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6911    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4780    0.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9570    0.7157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4662    1.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0280   -0.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7141    2.1656    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7809    0.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2009    0.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0259    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4320    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0070    1.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1834    1.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2569    0.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7398   -0.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
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 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
M  END

Alternative Forms

1. Parent:

   

   ALA1086120

   4-[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: 389.40

Molecular Weight (Monoisotopic): 389.0810

AlogP: 4.41

#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: 11.84

CX Basic pKa: ┄

CX LogP: 5.02

CX LogD: 5.02

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.71

Np Likeness Score: -1.45

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