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

ID: ALA4781454

PubChem CID: 162664221

Max Phase: Preclinical

Molecular Formula: C19H12ClNO3

Molecular Weight: 337.76

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1CC(c2ccc(Cl)cc2)C2=C(N1)c1ccccc1C(=O)C2=O

Standard InChI:  InChI=1S/C19H12ClNO3/c20-11-7-5-10(6-8-11)14-9-15(22)21-17-12-3-1-2-4-13(12)18(23)19(24)16(14)17/h1-8,14H,9H2,(H,21,22)

Standard InChI Key:  WVJIMLUOYWXSTO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   10.5365   -2.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8235   -1.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5375   -2.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8233   -3.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8236   -4.1213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5364   -4.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2464   -4.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2478   -3.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1171   -2.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1177   -2.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4088   -1.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6989   -2.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7023   -2.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4118   -3.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5355   -5.3582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2441   -1.6572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8201   -0.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9590   -2.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6661   -3.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3768   -2.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3779   -2.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6624   -1.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9547   -2.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0854   -1.6621    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 10  2  1  0
  9  4  1  0
  3  1  1  0
  1  2  1  0
  3  4  2  0
  3  8  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  6 15  2  0
  1 16  2  0
  2 17  2  0
  8 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781454

   ---

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: 337.76

Molecular Weight (Monoisotopic): 337.0506

AlogP: 3.12

#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: 2.85

CX LogD: 2.85

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.81

Np Likeness Score: -0.13

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