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

ID: ALA4776486

PubChem CID: 162643195

Max Phase: Preclinical

Molecular Formula: C20H15NO3

Molecular Weight: 317.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccccc1C1CC(=O)NC2=C1C(=O)C(=O)c1ccccc12

Standard InChI:  InChI=1S/C20H15NO3/c1-11-6-2-3-7-12(11)15-10-16(22)21-18-13-8-4-5-9-14(13)19(23)20(24)17(15)18/h2-9,15H,10H2,1H3,(H,21,22)

Standard InChI Key:  GODHNWDVFFKBCR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   19.3646  -16.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6516  -15.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3656  -16.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6515  -17.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6517  -18.1374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3645  -18.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0746  -18.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0760  -17.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9453  -16.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9458  -16.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2370  -15.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5271  -16.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5305  -16.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2399  -17.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3637  -19.3743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0722  -15.6732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6483  -14.8507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7871  -16.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4943  -17.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2049  -16.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2060  -16.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4905  -15.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7828  -16.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4909  -18.1351    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
 19 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776486

   ---

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: 317.34

Molecular Weight (Monoisotopic): 317.1052

AlogP: 2.78

#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: 2.76

CX LogD: 2.76

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.82

Np Likeness Score: 0.02

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