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

ID: ALA4751251

PubChem CID: 162651527

Max Phase: Preclinical

Molecular Formula: C19H14F3NO2S

Molecular Weight: 377.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCSC1=C(Nc2cccc(C(F)(F)F)c2)C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C19H14F3NO2S/c1-2-26-18-15(16(24)13-8-3-4-9-14(13)17(18)25)23-12-7-5-6-11(10-12)19(20,21)22/h3-10,23H,2H2,1H3

Standard InChI Key:  HQBCMGVBWDMPRF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   11.4242   -9.7650    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.8369   -9.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0193   -9.0547    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.0092   -6.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7142   -7.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7142   -7.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0092   -8.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3001   -7.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5910   -8.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8819   -7.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8819   -7.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5910   -6.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3001   -7.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0092   -5.7936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0092   -9.0624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4233   -8.2452    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4233   -9.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4233   -6.6108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1282   -7.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1282   -7.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8373   -8.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5464   -7.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5464   -7.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8373   -6.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5450   -9.4710    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.7088   -9.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  4 13  1  0
  8 13  2  0
  4 14  2  0
  7 15  2  0
 16 17  1  0
  6 16  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 21  2  1  0
 18 19  1  0
  5 18  1  0
  2 25  1  0
 17 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4751251

   ---

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: 377.39

Molecular Weight (Monoisotopic): 377.0697

AlogP: 5.16

#Rotatable Bonds: 4

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: 11.34

CX Basic pKa: ┄

CX LogP: 3.92

CX LogD: 3.92

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.80

Np Likeness Score: -1.07

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