4-[3-(4-Cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]benzoic Acid Methyl Ester

ID: ALA1084157

Cas Number: 915087-15-9

PubChem CID: 15951526

Max Phase: Preclinical

Molecular Formula: C21H16F3N3O3S

Molecular Weight: 447.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(N2C(=S)N(c3ccc(C#N)c(C(F)(F)F)c3)C(=O)C2(C)C)cc1

Standard InChI:  InChI=1S/C21H16F3N3O3S/c1-20(2)18(29)26(15-9-6-13(11-25)16(10-15)21(22,23)24)19(31)27(20)14-7-4-12(5-8-14)17(28)30-3/h4-10H,1-3H3

Standard InChI Key:  YIMGOTKXGRSQTQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.9403  -15.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3675  -15.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6521  -15.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2246  -15.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5100  -15.0195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2243  -17.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.8204  -16.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3822  -18.4696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0683  -16.1052    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.1351  -17.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5551  -18.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3801  -18.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7862  -17.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3612  -16.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5376  -16.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8250  -19.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5417  -18.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6111  -17.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0322  -18.2295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0150  -16.8006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6283  -18.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0
 16 17  1  0
 17 14  1  0
  5 14  1  0
 15 18  2  0
  3 10  1  0
 17 19  2  0
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  5  6  1  0
 10 11  1  0
 20 21  2  0
  3  4  1  0
 21 22  1  0
 10 12  1  0
 22 23  2  0
  6  7  2  0
 23 24  1  0
 10 13  1  0
 24 25  2  0
 25 20  1  0
 14 15  1  0
  7  2  1  0
  1 26  1  0
  2  3  2  0
  1 27  1  0
  4  5  2  0
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  8  9  3  0
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  2  8  1  0
 28 30  2  0
 15  1  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1084157

   4-[3-(4-Cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxo-imidazolidin-1-yl]benzoic acid methyl ester

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: 447.44

Molecular Weight (Monoisotopic): 447.0864

AlogP: 4.28

#Rotatable Bonds: 3

Polar Surface Area: 73.64

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.94

CX LogD: 4.94

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.52

Np Likeness Score: -1.07

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