2-(2-(dimethylamino)ethyl)-6-morpholino-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione

ID: ALA5271947

Max Phase: Preclinical

Molecular Formula: C20H22N4O5

Molecular Weight: 398.42

Names and Identifiers

Canonical SMILES:  CN(C)CCN1C(=O)c2cccc3c(N4CCOCC4)c([N+](=O)[O-])cc(c23)C1=O

Standard InChI:  InChI=1S/C20H22N4O5/c1-21(2)6-7-23-19(25)14-5-3-4-13-17(14)15(20(23)26)12-16(24(27)28)18(13)22-8-10-29-11-9-22/h3-5,12H,6-11H2,1-2H3

Standard InChI Key:  YICITURDSUXCOR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -0.7127   -0.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    0.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -0.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176   -1.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0068   -1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4331   -1.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1346   -0.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4218    0.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268    1.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114    1.4430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0024    1.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7178    1.4404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    2.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406    1.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4253   -1.4468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406   -1.0356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4238   -2.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0068   -2.2709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7213   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7213   -3.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0067   -3.9212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7078   -3.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7078   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4237    2.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4222    3.5073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1360    3.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7075    3.9199    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
  6  5  2  0
  1  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  3 13  1  0
 13 14  2  0
 12 15  1  0
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 17  1  1  0
 17 18  1  0
 17 19  2  0
 20  6  1  0
 20 21  1  0
 22 21  1  0
 23 22  1  0
 24 23  1  0
 20 25  1  0
 25 24  1  0
 15 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
M  CHG  2  17   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5271947

   ---

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: 398.42

Molecular Weight (Monoisotopic): 398.1590

AlogP: 1.74

#Rotatable Bonds: 5

Polar Surface Area: 96.23

Molecular Species: BASE

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.52

CX LogP: 1.75

CX LogD: 0.61

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: -1.33

References

1. Chen XM, Zhou JY, Liu SQ, Song LH, Wang HL, Wang Q, Liang SM, Lu L, Wei JH, Huang R, Zhang Y..  (2023)  Design, synthesis, and antitumor evaluation of morpholine substituted bisnaphthalimides as DNA targeting agents.,  85  [PMID:36894107] [10.1016/j.bmcl.2023.129218]

Source

Source(1):

• Scientific Literature