4-[3-(4-Cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]-N-methylbenzamide

ID: ALA1084516

Cas Number: 915087-16-0

PubChem CID: 15951527

Max Phase: Preclinical

Molecular Formula: C21H17F3N4O2S

Molecular Weight: 446.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H17F3N4O2S/c1-20(2)18(30)27(15-9-6-13(11-25)16(10-15)21(22,23)24)19(31)28(20)14-7-4-12(5-8-14)17(29)26-3/h4-10H,1-3H3,(H,26,29)

Standard InChI Key:  GOTJOTNPYGBVOP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -3.2889  -20.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2901  -21.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8588  -21.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8617  -20.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771  -20.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0046  -20.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7192  -19.9195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0049  -21.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2178  -21.1922    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1912  -22.0538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1839  -22.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0820  -22.4551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4088  -21.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8470  -23.3696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1609  -21.0052    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1509  -23.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5570  -22.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320  -21.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084  -21.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4042  -23.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125  -23.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3819  -22.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7858  -21.7006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8030  -23.1295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3991  -23.8489    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
 16 20  1  0
  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
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 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
 23 28  1  0
  8  9  3  0
 28 29  2  0
  2  8  1  0
 28 30  1  0
 15  1  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1084516

   Enzalutamide Impurity I

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: 446.45

Molecular Weight (Monoisotopic): 446.1024

AlogP: 3.85

#Rotatable Bonds: 3

Polar Surface Area: 76.44

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.01

CX LogD: 4.01

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.73

Np Likeness Score: -1.28

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