5-(2-(diethylamino)ethyl)-9-(1H-indol-3-yl)benzo[de]imidazo[4,5-g]isoquinoline-4,6(5H,8H)-dione

ID: ALA5278160

Max Phase: Preclinical

Molecular Formula: C27H25N5O2

Molecular Weight: 451.53

Names and Identifiers

Canonical SMILES:  CCN(CC)CCN1C(=O)c2cccc3c2c(cc2[nH]c(-c4c[nH]c5ccccc45)nc23)C1=O

Standard InChI:  InChI=1S/C27H25N5O2/c1-3-31(4-2)12-13-32-26(33)18-10-7-9-17-23(18)19(27(32)34)14-22-24(17)30-25(29-22)20-15-28-21-11-6-5-8-16(20)21/h5-11,14-15,28H,3-4,12-13H2,1-2H3,(H,29,30)

Standard InChI Key:  ATAFLLJZBCVRPD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   -4.8136    1.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0992    1.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3847    1.4385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3847    2.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0992    2.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6702    1.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6702    0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9558   -0.2114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5193   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1951    0.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9067   -0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9067   -1.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1969   -1.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5193   -1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2336   -1.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9558   -1.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650   -1.4518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2336   -2.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5103   -2.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1969   -2.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6895   -1.2719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1815   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107    0.0489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0064   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4189    0.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2402   -0.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3211   -0.8767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613   -1.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8136    0.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5588    1.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7412    1.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701    0.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  3  4  1  0
  4  5  1  0
  6  3  1  0
  7  6  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
  8 17  1  0
 17 18  2  0
 16 19  2  0
 19 20  1  0
 20 21  2  0
 14 21  1  0
 13 22  1  0
 22 23  2  0
 24 23  1  0
 12 24  1  0
 25 23  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 29 28  1  0
 25 29  2  0
 27 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 26 33  1  0
  9 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278160

   ---

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: 451.53

Molecular Weight (Monoisotopic): 451.2008

AlogP: 4.80

#Rotatable Bonds: 6

Polar Surface Area: 85.09

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.76

CX Basic pKa: 9.37

CX LogP: 3.49

CX LogD: 2.37

Aromatic Rings: 5

Heavy Atoms: 34

QED Weighted: 0.36

Np Likeness Score: -0.74

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