3-(4-Cyanophenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide

ID: ALA4525698

PubChem CID: 76642967

Max Phase: Preclinical

Molecular Formula: C18H14F3N3O5

Molecular Weight: 409.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(O)(COc1ccc(C#N)cc1)C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1

Standard InChI:  InChI=1S/C18H14F3N3O5/c1-17(26,10-29-13-5-2-11(9-22)3-6-13)16(25)23-12-4-7-15(24(27)28)14(8-12)18(19,20)21/h2-8,26H,10H2,1H3,(H,23,25)

Standard InChI Key:  WSJFKYDVPPVJFF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   30.4493  -12.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4481  -12.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1562  -13.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8658  -12.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8630  -12.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1544  -11.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7401  -13.3079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0327  -12.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3247  -13.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0334  -12.0816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6173  -12.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7391  -13.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8989  -13.8840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2019  -12.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2022  -12.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4995  -11.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7956  -12.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7987  -12.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5020  -13.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5742  -13.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5755  -14.1241    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.2813  -12.8972    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.2778  -13.7148    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.5713  -11.6642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5682  -10.8470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2805  -12.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0873  -11.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3787  -11.2740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
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  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  2  2  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
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 10 13  1  0
 10 14  1  0
  1 15  1  0
 15 16  2  0
 16 17  1  0
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 18 19  1  0
 19 20  2  0
 20 15  1  0
  5 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 25 26  2  0
 25 27  1  0
  6 25  1  0
 28 29  3  0
 18 28  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4525698

   3-(4-cyanophenoxy)-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 409.32

Molecular Weight (Monoisotopic): 409.0886

AlogP: 3.25

#Rotatable Bonds: 6

Polar Surface Area: 125.49

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.59

CX Basic pKa: ┄

CX LogP: 3.36

CX LogD: 3.36

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: -1.41

References

1. Bassetto M, Ferla S, Pertusati F, Kandil S, Westwell AD, Brancale A, McGuigan C..  (2016)  Design and synthesis of novel bicalutamide and enzalutamide derivatives as antiproliferative agents for the treatment of prostate cancer.,  118  [PMID:27131065] [10.1016/j.ejmech.2016.04.052]

Source

Source(1):

• Scientific Literature