2-((4-Fluoro-3-(trifluoromethyl)phenyl)amino)-3-((trifluoromethyl)thio)naphthalene-1,4-dione

ID: ALA4759087

PubChem CID: 162658926

Max Phase: Preclinical

Molecular Formula: C18H8F7NO2S

Molecular Weight: 435.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C(Nc2ccc(F)c(C(F)(F)F)c2)=C(SC(F)(F)F)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C18H8F7NO2S/c19-12-6-5-8(7-11(12)17(20,21)22)26-13-14(27)9-3-1-2-4-10(9)15(28)16(13)29-18(23,24)25/h1-7,26H

Standard InChI Key:  WVMBIIZJUWFAKH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   15.1207   -5.7006    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.7123   -6.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2995   -5.7032    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.0291   -8.8880    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.8541   -8.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4416   -9.6024    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.4285   -6.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1402   -6.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1402   -7.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4285   -8.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7126   -7.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9968   -8.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2851   -7.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2851   -6.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9968   -6.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7126   -6.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4285   -5.5862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4285   -8.8861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8561   -8.0611    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.8561   -6.4111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5720   -6.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2836   -6.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9995   -6.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9995   -7.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2836   -8.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5720   -7.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5705   -9.2986    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.4295   -6.8242    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.7138   -8.0614    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  7 16  1  0
 11 16  2  0
  7 17  2  0
 10 18  2  0
 19  5  1  0
  9 19  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 23  2  1  0
 20 21  1  0
  8 20  1  0
  5 27  1  0
  2 28  1  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4759087

   ---

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: 435.32

Molecular Weight (Monoisotopic): 435.0164

AlogP: 5.80

#Rotatable Bonds: 3

Polar Surface Area: 46.17

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.03

CX Basic pKa: ┄

CX LogP: 5.15

CX LogD: 5.15

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.62

Np Likeness Score: -1.09

References

1. Varricchio C,Beirne K,Aeschlimann P,Heard C,Rozanowska M,Votruba M,Brancale A.  (2020)  Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber's Hereditary Optic Neuropathy (LHON).,  63  (22): [PMID:33180495] [10.1021/acs.jmedchem.0c00942]

Source

Source(1):

• Scientific Literature