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

ID: ALA4472078

PubChem CID: 155535476

Max Phase: Preclinical

Molecular Formula: C17H10F3NO3

Molecular Weight: 333.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C(O)=C(Nc2cccc(C(F)(F)F)c2)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C17H10F3NO3/c18-17(19,20)9-4-3-5-10(8-9)21-13-14(22)11-6-1-2-7-12(11)15(23)16(13)24/h1-8,21,24H

Standard InChI Key:  AAGUTQXRQQTPPA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   17.8689  -10.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8677  -11.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5826  -11.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5807  -10.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2961  -10.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2949  -11.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0078  -11.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7265  -11.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7277  -10.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0101  -10.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0102   -9.4056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0056  -12.7124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4432  -10.2373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4398  -11.8910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1554  -11.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8659  -11.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5809  -11.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5838  -10.6630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8654  -10.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1533  -10.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2941  -11.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2913  -12.7287    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.0099  -11.4936    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.0035  -12.3122    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  7 12  2  0
  9 13  1  0
  8 14  1  0
 14 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
 17 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4472078

   ---

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: 333.26

Molecular Weight (Monoisotopic): 333.0613

AlogP: 3.97

#Rotatable Bonds: 2

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.98

CX Basic pKa: ┄

CX LogP: 2.77

CX LogD: 1.33

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.87

Np Likeness Score: -0.66

References

1. Calil FA, David JS, Chiappetta ERC, Fumagalli F, Mello RB, Leite FHA, Castilho MS, Emery FS, Nonato MC..  (2019)  Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.,  167  [PMID:30776695] [10.1016/j.ejmech.2019.02.018]

Source

Source(1):

• Scientific Literature