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

ID: ALA5269853

Max Phase: Preclinical

Molecular Formula: C18H17N3O6

Molecular Weight: 371.35

Names and Identifiers

Canonical SMILES:  O=C1c2cccc3c(N4CCOCC4)c([N+](=O)[O-])cc(c23)C(=O)N1CCO

Standard InChI:  InChI=1S/C18H17N3O6/c22-7-4-20-17(23)12-3-1-2-11-15(12)13(18(20)24)10-14(21(25)26)16(11)19-5-8-27-9-6-19/h1-3,10,22H,4-9H2

Standard InChI Key:  JNECHXNVCQPXNY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -0.7127   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176   -0.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0068   -1.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4331   -1.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395   -0.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1346    0.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4218    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268    1.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0024    1.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7178    1.6474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    2.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406    1.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4253   -1.2398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0068   -2.0639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7213   -2.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7213   -3.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0067   -3.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7078   -3.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7078   -2.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4237    2.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4222    3.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  5  4  1  0
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 17 18  1  0
 17 19  2  0
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 20 21  1  0
 22 21  1  0
 23 22  1  0
 24 23  1  0
 20 25  1  0
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 26 27  1  0
M  CHG  2  17   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5269853

   ---

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: 371.35

Molecular Weight (Monoisotopic): 371.1117

AlogP: 1.17

#Rotatable Bonds: 4

Polar Surface Area: 113.22

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.05

CX LogD: 1.05

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: -1.13

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