2-Hydroxy-2-methyl-N-(4-nitro-2-(trifluoromethyl)phenyl)-3-((2-(trifluoromethoxy)phenyl)thio)propanamide

ID: ALA4555717

PubChem CID: 155556863

Max Phase: Preclinical

Molecular Formula: C18H14F6N2O5S

Molecular Weight: 484.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(O)(CSc1ccccc1OC(F)(F)F)C(=O)Nc1ccc([N+](=O)[O-])cc1C(F)(F)F

Standard InChI:  InChI=1S/C18H14F6N2O5S/c1-16(28,9-32-14-5-3-2-4-13(14)31-18(22,23)24)15(27)25-12-7-6-10(26(29)30)8-11(12)17(19,20)21/h2-8,28H,9H2,1H3,(H,25,27)

Standard InChI Key:  QYGXWJVCHFRKKM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   26.5092  -21.2965    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.0531  -20.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0519  -20.8943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7600  -21.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4696  -20.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4668  -20.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7582  -19.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3439  -21.3024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6365  -20.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9285  -21.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6371  -20.0760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2211  -20.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3429  -21.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5026  -21.8784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8057  -20.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8060  -20.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1033  -19.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3993  -20.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4025  -20.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1058  -21.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7598  -22.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0520  -22.5289    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.4674  -22.5293    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.7520  -22.9350    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.1751  -19.6586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1720  -18.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8843  -20.0645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1098  -22.1172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4042  -22.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4082  -23.3465    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.6944  -22.1242    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.6903  -22.9309    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  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
 12  1  1  0
 10 13  1  0
 10 14  1  0
  1 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  4 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
 20 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4555717

   ---

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: 484.37

Molecular Weight (Monoisotopic): 484.0528

AlogP: 4.99

#Rotatable Bonds: 7

Polar Surface Area: 101.70

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.14

CX Basic pKa: ┄

CX LogP: 5.46

CX LogD: 5.46

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.25

Np Likeness Score: -1.34

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