diethyl ((4-((1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)methyl)-1H-1,2,3-triazol-1-yl)methyl)phosphonate

ID: ALA5285780

Max Phase: Preclinical

Molecular Formula: C20H21N4O5P

Molecular Weight: 428.39

Names and Identifiers

Canonical SMILES:  CCOP(=O)(Cn1cc(CN2C(=O)c3cccc4cccc(c34)C2=O)nn1)OCC

Standard InChI:  InChI=1S/C20H21N4O5P/c1-3-28-30(27,29-4-2)13-23-11-15(21-22-23)12-24-19(25)16-9-5-7-14-8-6-10-17(18(14)16)20(24)26/h5-11H,3-4,12-13H2,1-2H3

Standard InChI Key:  ZQGRIDXDDJMWHQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    0.2310   -2.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2310   -3.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9443   -3.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -3.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -2.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9426   -1.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9426   -1.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6529   -0.6857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3611   -1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3611   -1.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0748   -2.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0748   -3.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3662   -3.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0713   -0.6863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6529    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436    0.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2342    0.1333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799    0.7005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0516    1.4296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664    1.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4612    2.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2804    2.1390    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6899    2.8484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5090    2.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9186    3.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4924    1.3478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0716    1.9270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2835    1.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0748    0.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2339   -0.6850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  2  0
  6  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
  5 10  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
  4 13  1  0
  9 14  2  0
  8 15  1  0
 15 16  1  0
 17 16  1  0
 17 18  2  0
 18 19  1  0
 20 19  1  0
 16 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 22 26  2  0
 22 27  1  0
 27 28  1  0
 28 29  1  0
  7 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285780

   ---

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: 428.39

Molecular Weight (Monoisotopic): 428.1250

AlogP: 3.45

#Rotatable Bonds: 8

Polar Surface Area: 103.62

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.09

CX LogP: 2.17

CX LogD: 2.17

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.40

Np Likeness Score: -1.02

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