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

ID: ALA4778793

PubChem CID: 162661852

Max Phase: Preclinical

Molecular Formula: C19H13NO4

Molecular Weight: 319.32

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H13NO4/c21-11-5-3-4-10(8-11)14-9-15(22)20-17-12-6-1-2-7-13(12)18(23)19(24)16(14)17/h1-8,14,21H,9H2,(H,20,22)

Standard InChI Key:  PQUVOZPXTFTIPQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   10.8997   -9.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1867   -9.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9007  -10.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1865  -10.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1868  -11.7030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8996  -12.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6096  -11.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6110  -10.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4803  -10.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4809   -9.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7720   -9.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0621   -9.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0655  -10.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7750  -10.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8987  -12.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6073   -9.2389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1833   -8.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3221  -10.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0293  -10.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7400  -10.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7411   -9.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0256   -9.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3179   -9.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0234   -8.4248    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA4778793

   ---

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: 319.32

Molecular Weight (Monoisotopic): 319.0845

AlogP: 2.17

#Rotatable Bonds: 1

Polar Surface Area: 83.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.44

CX Basic pKa: ┄

CX LogP: 1.94

CX LogD: 1.94

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.79

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