4-(3-Trifluoromethylphenyl)-3,4-dihydrobenzo[h]quinoline-2,5,6(1H)-trione

ID: ALA4778568

PubChem CID: 162662052

Max Phase: Preclinical

Molecular Formula: C20H12F3NO3

Molecular Weight: 371.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1CC(c2cccc(C(F)(F)F)c2)C2=C(N1)c1ccccc1C(=O)C2=O

Standard InChI:  InChI=1S/C20H12F3NO3/c21-20(22,23)11-5-3-4-10(8-11)14-9-15(25)24-17-12-6-1-2-7-13(12)18(26)19(27)16(14)17/h1-8,14H,9H2,(H,24,25)

Standard InChI Key:  ORIBAEXUUGYBEN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   27.6483   -8.5846    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.4655   -8.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0569   -7.8769    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.3437   -9.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6308   -9.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3448  -10.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6306  -11.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6309  -11.8640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3437  -12.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0537  -11.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0551  -11.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9244  -10.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9250   -9.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2161   -9.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5062   -9.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5096  -10.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2190  -11.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3428  -13.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0513   -9.3998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6274   -8.5774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7662  -10.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4734  -11.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1841  -10.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1852   -9.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4697   -9.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7620   -9.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1741   -8.1752    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
 13  5  1  0
 12  7  1  0
  6  4  1  0
  4  5  1  0
  6  7  2  0
  6 11  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  9 18  2  0
  4 19  2  0
  5 20  2  0
 11 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 25  2  1  0
  2 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4778568

   ---

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: 371.31

Molecular Weight (Monoisotopic): 371.0769

AlogP: 3.49

#Rotatable Bonds: 1

Polar Surface Area: 63.24

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.56

CX Basic pKa: ┄

CX LogP: 3.12

CX LogD: 3.12

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.78

Np Likeness Score: -0.36

References

1. Wu LQ,Ma X,Zhang C,Liu ZP.  (2020)  Design, synthesis, and biological evaluation of 4-substituted-3,4-dihydrobenzo[h]quinoline-2,5,6(1H)-triones as NQO1-directed antitumor agents.,  198  [PMID:32464425] [10.1016/j.ejmech.2020.112396]

Source

Source(1):

• Scientific Literature