5-methoxy-4,6-dinitro-7H-dibenzo[de,h]quinolin-7-one

ID: ALA2332982

PubChem CID: 71719422

Max Phase: Preclinical

Molecular Formula: C17H9N3O6

Molecular Weight: 351.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c([N+](=O)[O-])c2c3c(nccc3c1[N+](=O)[O-])-c1ccccc1C2=O

Standard InChI:  InChI=1S/C17H9N3O6/c1-26-17-14(19(22)23)10-6-7-18-13-8-4-2-3-5-9(8)16(21)12(11(10)13)15(17)20(24)25/h2-7H,1H3

Standard InChI Key:  FJWVMHXQYQHHQW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   11.5135   -6.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5124   -7.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2204   -7.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2187   -6.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9273   -6.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9307   -7.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6430   -7.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3561   -7.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0707   -7.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7830   -7.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7761   -6.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6363   -6.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3528   -6.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0668   -6.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0706   -5.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3540   -5.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6337   -5.4635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6455   -8.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4933   -7.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4985   -8.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0752   -8.7544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7848   -9.1597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3693   -9.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4805   -6.2708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4715   -5.4536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1926   -6.6716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 12  1  0
  6  7  1  0
  7  8  1  0
 13  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 14  2  0
 12 13  1  0
 12 17  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  7 18  2  0
 10 19  1  0
 19 20  1  0
 21 22  2  0
 21 23  1  0
  9 21  1  0
 24 25  2  0
 24 26  1  0
 11 24  1  0
M  CHG  4  21   1  23  -1  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2332982

   11-Methoxy-10,12-dinitro-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-8-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 351.27

Molecular Weight (Monoisotopic): 351.0491

AlogP: 3.27

#Rotatable Bonds: 3

Polar Surface Area: 125.47

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.84

CX LogP: 2.99

CX LogD: 2.99

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.41

Np Likeness Score: 0.24

References

1. Castro-Castillo V, Suárez-Rozas C, Castro-Loiza N, Theoduloz C, Cassels BK..  (2013)  Annulation of substituted anthracene-9,10-diones yields promising selectively antiproliferative compounds.,  62  [PMID:23454511] [10.1016/j.ejmech.2013.01.049]

Source

Source(1):

• Scientific Literature