3-((3,4-Difluorophenyl)thio)-2-hydroxy-2-methyl-N-(4-nitro-2-(trifluoromethyl)phenyl)propanamide

ID: ALA4549796

PubChem CID: 155550281

Max Phase: Preclinical

Molecular Formula: C17H13F5N2O4S

Molecular Weight: 436.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(O)(CSc1ccc(F)c(F)c1)C(=O)Nc1ccc([N+](=O)[O-])cc1C(F)(F)F

Standard InChI:  InChI=1S/C17H13F5N2O4S/c1-16(26,8-29-10-3-4-12(18)13(19)7-10)15(25)23-14-5-2-9(24(27)28)6-11(14)17(20,21)22/h2-7,26H,8H2,1H3,(H,23,25)

Standard InChI Key:  JGEITDDJBCVTLM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   15.8343  -20.4053    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.4122  -19.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4111  -19.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1259  -20.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8424  -19.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8396  -19.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1242  -18.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6963  -20.4113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9821  -19.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2671  -20.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9827  -19.1732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5530  -19.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6760  -20.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8469  -20.9929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1239  -19.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1242  -19.1781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4148  -18.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7041  -19.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7073  -20.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4174  -20.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1257  -21.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4111  -21.6497    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.8401  -21.6500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.1179  -22.0596    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.5547  -18.7517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5515  -17.9266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2707  -19.1616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9946  -20.4189    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.9888  -18.7681    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
 19 28  1  0
 18 29  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4549796

   ---

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: 436.36

Molecular Weight (Monoisotopic): 436.0516

AlogP: 4.37

#Rotatable Bonds: 6

Polar Surface Area: 92.47

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.14

CX Basic pKa: ┄

CX LogP: 4.31

CX LogD: 4.31

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.30

Np Likeness Score: -1.67

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