2-(2-((6-(1-(4-chlorobenzoyl)-6-methoxy-2-methyl-2,7a-dihydro-1H-indol-3-yl)-5-oxohexyl)amino)ethyl)-6-(dimethylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione

ID: ALA5288085

Max Phase: Preclinical

Molecular Formula: C39H41ClN4O5

Molecular Weight: 681.23

Names and Identifiers

Canonical SMILES:  COC1=CC2C(=C(CC(=O)CCCCNCCN3C(=O)c4cccc5c(N(C)C)ccc(c45)C3=O)C(C)N2C(=O)c2ccc(Cl)cc2)C=C1

Standard InChI:  InChI=1S/C39H41ClN4O5/c1-24-33(29-16-15-28(49-4)23-35(29)44(24)37(46)25-11-13-26(40)14-12-25)22-27(45)8-5-6-19-41-20-21-43-38(47)31-10-7-9-30-34(42(2)3)18-17-32(36(30)31)39(43)48/h7,9-18,23-24,35,41H,5-6,8,19-22H2,1-4H3

Standard InChI Key:  NNOUMQQFLJDIKT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 49 54  0  0  0  0  0  0  0  0999 V2000
   -2.5634   -4.2093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9797   -3.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5677   -2.7650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7350   -2.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3188   -2.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862   -2.0440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0699   -1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626   -1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1790   -0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115   -0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279    0.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2605    0.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6767    0.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2605    1.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8369    2.1855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5781    1.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4849    1.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1614    0.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9256    0.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0165    1.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3427    2.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7376    2.1053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7376    2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6214    2.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8172    3.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2282    2.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4267    2.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2111    3.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    4.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008    4.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4069    3.8522    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2102    3.5784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279    1.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115    0.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881   -2.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5717   -1.3255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8204   -2.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2325   -2.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160   -3.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2341   -4.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0663   -4.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4886   -3.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0689   -2.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4851   -2.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0693   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2362   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3213   -3.5022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7376   -2.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7376   -4.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 14 13  1  0
 14 15  1  0
 15 16  1  0
 17 16  1  0
 13 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 16 21  1  0
 20 22  1  0
 22 23  1  0
 15 24  1  0
 24 25  1  0
 26 25  2  0
 27 26  1  0
 28 27  2  0
 29 28  1  0
 30 29  2  0
 25 30  1  0
 28 31  1  0
 24 32  2  0
 14 33  1  0
 11 34  2  0
  3 35  1  0
 35 36  2  0
 37 35  1  0
 38 37  2  0
 38 39  1  0
 39  2  1  0
 40 39  2  0
 41 40  1  0
 42 41  2  0
 43 42  1  0
 43 38  1  0
 44 43  2  0
 45 44  1  0
 46 45  2  0
 37 46  1  0
 42 47  1  0
 47 48  1  0
 47 49  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5288085

   ---

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: 681.23

Molecular Weight (Monoisotopic): 680.2765

AlogP: 6.18

#Rotatable Bonds: 13

Polar Surface Area: 99.26

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 9.72

CX LogP: 4.70

CX LogD: 2.43

Aromatic Rings: 3

Heavy Atoms: 49

QED Weighted: 0.17

Np Likeness Score: -0.31

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