[amino-[2-[6-[2-[[amino(azaniumylidene)methyl]amino]ethylamino]-1,3-dioxo-benzo[de]isoquinolin-2-yl]ethylamino]methylene]ammonium

ID: ALA5285566

Max Phase: Preclinical

Molecular Formula: C18H22N8O2

Molecular Weight: 382.43

Names and Identifiers

Canonical SMILES:  N=C(N)NCCNc1ccc2c3c(cccc13)C(=O)N(CCNC(=N)N)C2=O

Standard InChI:  InChI=1S/C18H22N8O2/c19-17(20)24-7-6-23-13-5-4-12-14-10(13)2-1-3-11(14)15(27)26(16(12)28)9-8-25-18(21)22/h1-5,23H,6-9H2,(H4,19,20,24)(H4,21,22,25)

Standard InChI Key:  WFUNXNALWINACB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -0.3579   -0.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565    0.4065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -0.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -0.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3584   -1.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3579   -0.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0735   -1.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912   -0.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7931   -0.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0786    0.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0788    1.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584    1.6582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3622    1.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0826    1.6583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7992    1.6579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584    2.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619    2.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619    3.7378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3584   -2.0741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3619   -2.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3619   -3.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0823   -3.7378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0823    4.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0823    4.9855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8027    3.7378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0823   -4.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8027   -4.9855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3619   -4.9855    0.0000 N   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
  6  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  1 10  1  0
 10 11  1  0
 12 11  1  0
 13 12  1  0
  2 13  1  0
 13 14  2  0
 11 15  2  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285566

   ---

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: 382.43

Molecular Weight (Monoisotopic): 382.1866

AlogP: -0.19

#Rotatable Bonds: 7

Polar Surface Area: 173.21

Molecular Species: BASE

HBA: 5

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 12.07

CX LogP: -0.88

CX LogD: -5.70

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.15

Np Likeness Score: -0.88

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