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

ID: ALA4541556

PubChem CID: 155551497

Max Phase: Preclinical

Molecular Formula: C18H14F6N2O6S

Molecular Weight: 500.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(O)(CS(=O)(=O)c1ccc(C(F)(F)F)cc1)C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1

Standard InChI:  InChI=1S/C18H14F6N2O6S/c1-16(28,9-33(31,32)12-5-2-10(3-6-12)17(19,20)21)15(27)25-11-4-7-14(26(29)30)13(8-11)18(22,23)24/h2-8,28H,9H2,1H3,(H,25,27)

Standard InChI Key:  MGXFOLLDXHFBKO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
   16.0127  -20.8545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6044  -20.1419    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.1915  -20.8518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1821  -18.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1810  -19.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8958  -20.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6123  -19.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6094  -18.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8941  -18.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4662  -20.1479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7521  -19.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0373  -20.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7527  -18.9098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3231  -19.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7113  -20.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4696  -20.7590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8941  -19.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8944  -18.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1849  -18.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4743  -18.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4775  -19.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1876  -20.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3274  -20.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3287  -20.9719    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.0412  -19.7332    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.0378  -20.5586    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.3245  -18.4883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3214  -17.6633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0405  -18.8981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7590  -18.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7573  -17.6798    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.0454  -18.9188    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.0418  -18.0919    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  4  2  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14  2  1  0
 12 15  1  0
 12 16  1  0
  2 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  7 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 27 28  2  0
 27 29  1  0
  8 27  1  0
 20 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4541556

   ---

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: 500.37

Molecular Weight (Monoisotopic): 500.0477

AlogP: 3.80

#Rotatable Bonds: 6

Polar Surface Area: 126.61

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.52

CX Basic pKa: ┄

CX LogP: 3.53

CX LogD: 3.53

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.35

Np Likeness Score: -1.32

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