2-(3-chloropropyl)-6-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione

ID: ALA5286617

Max Phase: Preclinical

Molecular Formula: C15H11ClN2O4

Molecular Weight: 318.72

Names and Identifiers

Canonical SMILES:  O=C1c2cccc3c([N+](=O)[O-])ccc(c23)C(=O)N1CCCCl

Standard InChI:  InChI=1S/C15H11ClN2O4/c16-7-2-8-17-14(19)10-4-1-3-9-12(18(21)22)6-5-11(13(9)10)15(17)20/h1,3-6H,2,7-8H2

Standard InChI Key:  LLJBMNWXSOWIFM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    1.4280    0.8307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7139    0.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002    0.8276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002    1.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7158    2.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7158    2.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313    3.3062    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168    0.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4310    0.8280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168   -0.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0018   -0.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7139   -0.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -1.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7190   -2.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0018   -1.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -2.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345   -1.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345   -0.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7190   -2.8930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4345   -3.3062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0035   -3.3062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  3  8  1  0
  8  9  2  0
 10  8  1  0
 11 10  1  0
 11 12  1  0
 12  2  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 16 15  1  0
 16 11  2  0
 17 16  1  0
 18 17  2  0
 19 18  1  0
 10 19  2  0
 20 15  1  0
 20 21  2  0
 20 22  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5286617

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 318.72

Molecular Weight (Monoisotopic): 318.0407

AlogP: 2.97

#Rotatable Bonds: 4

Polar Surface Area: 80.52

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.57

CX LogD: 2.57

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.38

Np Likeness Score: -1.14

References

1. Tomczyk MD, Walczak KZ..  (2018)  l,8-Naphthalimide based DNA intercalators and anticancer agents. A systematic review from 2007 to 2017.,  159  [PMID:30312931] [10.1016/j.ejmech.2018.09.055]

Source

Source(1):

• Scientific Literature