2,2'-(azanediylbis(ethane-2,1-diyl))bis(6-morpholino-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione)

ID: ALA5275285

Max Phase: Preclinical

Molecular Formula: C36H33N7O10

Molecular Weight: 723.70

Names and Identifiers

Canonical SMILES:  O=C1c2cccc3c(N4CCOCC4)c([N+](=O)[O-])cc(c23)C(=O)N1CCNCCN1C(=O)c2cccc3c(N4CCOCC4)c([N+](=O)[O-])cc(c23)C1=O

Standard InChI:  InChI=1S/C36H33N7O10/c44-33-23-5-1-3-21-29(23)25(19-27(42(48)49)31(21)38-11-15-52-16-12-38)35(46)40(33)9-7-37-8-10-41-34(45)24-6-2-4-22-30(24)26(36(41)47)20-28(43(50)51)32(22)39-13-17-53-18-14-39/h1-6,19-20,37H,7-18H2

Standard InChI Key:  ZVFQSPGMUPDLML-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 53 60  0  0  0  0  0  0  0  0999 V2000
   -4.6425    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9279    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2161    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2161    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9262    0.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6425    0.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5069    0.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5051   -0.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2106   -1.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9244   -0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5014    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7868    1.2374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7868    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5014    2.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0722   -0.0002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3572    1.6496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3572    2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0719    1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0722    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3570    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009    1.2374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6423    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6425   -0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9324   -1.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2158   -0.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6428    1.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3578    1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3596    0.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155    2.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863   -0.0002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9324   -2.0621    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2178   -2.4746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6471   -2.4746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3572   -0.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3572   -0.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0718   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7864   -0.8291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7864   -0.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0719    0.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3572   -1.2374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0718   -0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7864   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7864   -2.0626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0718   -2.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3572   -2.0626    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
  4  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  5 10  1  0
  3 11  1  0
 12 11  1  0
 13 12  1  0
  7 13  1  0
 11 14  2  0
 13 15  2  0
 16  1  1  0
 16 17  1  0
 16 18  2  0
 12 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 25 24  1  0
 26 25  1  0
 27 26  1  0
 28 27  2  0
 29 28  1  0
 24 29  1  0
 27 30  1  0
 31 30  2  0
 32 31  1  0
 33 32  2  0
 28 33  1  0
 26 34  2  0
 35 34  1  0
 36 35  2  0
 30 36  1  0
 25 37  2  0
 29 38  2  0
 39 32  1  0
 39 40  1  0
 39 41  2  0
 42  6  1  0
 42 43  1  0
 44 43  1  0
 45 44  1  0
 46 45  1  0
 42 47  1  0
 47 46  1  0
 48 31  1  0
 48 49  1  0
 50 49  1  0
 51 50  1  0
 52 51  1  0
 48 53  1  0
 53 52  1  0
M  CHG  4  16   1  17  -1  39   1  40  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5275285

   ---

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: 723.70

Molecular Weight (Monoisotopic): 723.2289

AlogP: 2.96

#Rotatable Bonds: 10

Polar Surface Area: 198.01

Molecular Species: BASE

HBA: 13

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 17

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.89

CX LogP: 2.94

CX LogD: 1.44

Aromatic Rings: 4

Heavy Atoms: 53

QED Weighted: 0.11

Np Likeness Score: -0.70

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