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

ID: ALA5286180

Max Phase: Preclinical

Molecular Formula: C25H21N5O2

Molecular Weight: 423.48

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H21N5O2/c1-29(2)10-11-30-24(31)16-8-5-7-15-21(16)17(25(30)32)12-20-22(15)28-23(27-20)18-13-26-19-9-4-3-6-14(18)19/h3-9,12-13,26H,10-11H2,1-2H3,(H,27,28)

Standard InChI Key:  YCWWQGYESDYKKS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 37  0  0  0  0  0  0  0  0999 V2000
   -2.6798   -0.8838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9667   -0.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9667    0.3634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6852    0.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4037    0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1221    0.7782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1221    1.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8405    0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2529    0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2529    1.6131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9119    0.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    0.6253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1936   -0.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4381    0.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1878    1.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7621    2.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5843    1.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8405    1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2639    0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3452   -0.3056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5813   -0.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6989   -0.7030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9119   -0.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979   -0.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979   -1.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5131   -2.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405   -1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405   -0.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5222   -0.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  1  0
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  6  7  1  0
  6  8  1  0
  9  3  1  0
  9 10  2  0
 11  9  1  0
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 19 18  2  0
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 16 24  2  0
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 26 13  2  0
 27 26  1  0
 27 28  1  0
 29 28  2  0
 30 29  1  0
 31 30  2  0
 31  2  1  0
 32 31  1  0
 32 27  2  0
 11 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286180

   ---

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: 423.48

Molecular Weight (Monoisotopic): 423.1695

AlogP: 4.02

#Rotatable Bonds: 4

Polar Surface Area: 85.09

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.17

CX Basic pKa: 8.41

CX LogP: 2.98

CX LogD: 2.18

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -0.65

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