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

ID: ALA4781550

PubChem CID: 162664235

Max Phase: Preclinical

Molecular Formula: C19H12ClNO3

Molecular Weight: 337.76

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1CC(c2ccccc2Cl)C2=C(N1)c1ccccc1C(=O)C2=O

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

Standard InChI Key:  RDALPVRWYVKZQZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    3.2395  -16.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5266  -16.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2406  -17.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5264  -18.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5266  -18.8803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394  -19.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9495  -18.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9509  -18.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202  -17.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8208  -16.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119  -16.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4020  -16.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4054  -17.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1148  -18.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2386  -20.1172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9471  -16.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5232  -15.5936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6620  -17.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3692  -18.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0798  -17.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0809  -16.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3655  -16.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6577  -16.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3658  -18.8780    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
 19 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781550

   ---

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: -0.14

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