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

ID: ALA4777825

PubChem CID: 162644038

Max Phase: Preclinical

Molecular Formula: C20H15NO5

Molecular Weight: 349.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(C2CC(=O)NC3=C2C(=O)C(=O)c2ccccc23)ccc1O

Standard InChI:  InChI=1S/C20H15NO5/c1-26-15-8-10(6-7-14(15)22)13-9-16(23)21-18-11-4-2-3-5-12(11)19(24)20(25)17(13)18/h2-8,13,22H,9H2,1H3,(H,21,23)

Standard InChI Key:  GKAKWVCYRJUUQF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   26.9752  -16.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2622  -15.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9763  -17.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2621  -17.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2623  -18.3520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9751  -18.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6852  -18.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6866  -17.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5559  -17.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5564  -16.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8476  -15.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1377  -16.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1411  -17.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8505  -17.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9743  -19.5889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6828  -15.8878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2589  -15.0654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3977  -17.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1049  -17.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8155  -17.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8166  -16.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1012  -15.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3934  -16.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0989  -15.0738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5241  -15.8928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8055  -14.6632    0.0000 C   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
 22 24  1  0
 21 25  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4777825

   ---

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: 349.34

Molecular Weight (Monoisotopic): 349.0950

AlogP: 2.18

#Rotatable Bonds: 2

Polar Surface Area: 92.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.94

CX Basic pKa: ┄

CX LogP: 1.78

CX LogD: 1.78

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.81

Np Likeness Score: 0.47

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