N-Methyl-4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]benzamide

ID: ALA1082405

PubChem CID: 15952000

Max Phase: Preclinical

Molecular Formula: C22H17F3N4O2S

Molecular Weight: 458.47

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)C23CCC3)cc1

Standard InChI:  InChI=1S/C22H17F3N4O2S/c1-27-18(30)13-3-6-15(7-4-13)29-20(32)28(19(31)21(29)9-2-10-21)16-8-5-14(12-26)17(11-16)22(23,24)25/h3-8,11H,2,9-10H2,1H3,(H,27,30)

Standard InChI Key:  IJXGISWNZBHSFJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   11.3835  -23.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0956  -24.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5121  -23.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3374  -20.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6224  -20.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.7896  -21.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3521  -23.1707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0374  -20.8075    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1037  -22.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5234  -22.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3480  -22.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7539  -22.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3291  -21.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5060  -21.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5784  -22.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9821  -21.5025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9993  -22.9307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5956  -23.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  5  6  2  0
  7  8  2  0
 11 12  3  0
  5 11  1  0
 18  1  1  0
  1 19  1  0
 19 20  1  0
 20 17  1  0
  8 17  1  0
 18 21  2  0
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  8  9  1  0
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  6  7  1  0
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  9 10  2  0
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 13 16  1  0
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 17 18  1  0
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  1  2  1  0
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  2  3  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1082405

   N-Methyl-4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]benzamide

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: 458.47

Molecular Weight (Monoisotopic): 458.1024

AlogP: 4.00

#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: 4.15

CX LogD: 4.15

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.70

Np Likeness Score: -1.22

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