2-[4-(8-methoxy-2-oxo-chromen-3-yl)thiazol-2-yl]benzo[de]isoquinoline-1,3-dione

ID: ALA5277748

Max Phase: Preclinical

Molecular Formula: C25H14N2O5S

Molecular Weight: 454.46

Names and Identifiers

Canonical SMILES:  COc1cccc2cc(-c3csc(N4C(=O)c5cccc6cccc(c56)C4=O)n3)c(=O)oc12

Standard InChI:  InChI=1S/C25H14N2O5S/c1-31-19-10-4-7-14-11-17(24(30)32-21(14)19)18-12-33-25(26-18)27-22(28)15-8-2-5-13-6-3-9-16(20(13)15)23(27)29/h2-12H,1H3

Standard InChI Key:  OFDMZVNVJIMNQM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 38  0  0  0  0  0  0  0  0999 V2000
   -3.0295   -2.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149   -2.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6030   -2.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6030   -3.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3131   -3.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0295   -3.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7414   -2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7414   -1.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0313   -0.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149   -1.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974   -0.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8799   -1.2086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8799   -2.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974    0.0338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1626   -2.4512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1626   -0.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5545   -1.2086    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756   -0.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8437    0.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164    0.0094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2578    0.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8437    1.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2578    2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0861    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    1.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0861    0.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0154    1.5366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994    2.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3278    2.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7414    2.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3319    1.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0853    3.6860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2570    3.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  1  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  2 10  1  0
 10 11  1  0
 12 11  1  0
 13 12  1  0
  3 13  1  0
 11 14  2  0
 13 15  2  0
 12 16  1  0
 17 16  1  0
 17 18  1  0
 18 19  2  0
 20 19  1  0
 16 20  2  0
 19 21  1  0
 22 21  1  0
 23 22  1  0
 24 23  1  0
 25 24  2  0
 26 25  1  0
 21 26  2  0
 22 27  2  0
 24 28  1  0
 29 28  2  0
 30 29  1  0
 31 30  2  0
 25 31  1  0
 28 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5277748

   ---

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: 454.46

Molecular Weight (Monoisotopic): 454.0623

AlogP: 4.88

#Rotatable Bonds: 3

Polar Surface Area: 89.71

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.61

CX LogD: 4.61

Aromatic Rings: 5

Heavy Atoms: 33

QED Weighted: 0.29

Np Likeness Score: -0.76

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