2,7-bis(4-(6-chloro-2-oxo-2H-chromen-3-yl)thiazol-2-yl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone

ID: ALA5287280

Max Phase: Preclinical

Molecular Formula: C38H14Cl2N4O8S2

Molecular Weight: 789.59

Names and Identifiers

Canonical SMILES:  O=C1c2ccc3c4c(ccc(c24)C(=O)N1c1nc(-c2cc4cc(Cl)ccc4oc2=O)cs1)C(=O)N(c1nc(-c2cc4cc(Cl)ccc4oc2=O)cs1)C3=O

Standard InChI:  InChI=1S/C38H14Cl2N4O8S2/c39-17-1-7-27-15(9-17)11-23(35(49)51-27)25-13-53-37(41-25)43-31(45)19-3-5-21-30-22(6-4-20(29(19)30)32(43)46)34(48)44(33(21)47)38-42-26(14-54-38)24-12-16-10-18(40)2-8-28(16)52-36(24)50/h1-14H

Standard InChI Key:  GAKYXVJRHSKXPC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 54 63  0  0  0  0  0  0  0  0999 V2000
    2.1065   -1.4954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6902   -0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1020   -0.0516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9345   -0.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4946   -0.6614    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2612   -0.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1796    0.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7683    1.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5759    0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1609    1.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9649    1.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5456    1.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3290    2.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281    2.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9449    2.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1405    2.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5531    1.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7489    2.0907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3498    1.6073    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3507    0.6693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819    0.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0982    1.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8501    0.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4384   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4367   -1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3949   -1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8169   -0.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462   -0.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0622   -0.0607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458    0.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0620    1.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8134    0.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978    1.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346    1.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3974   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8947   -0.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3288   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1526   -0.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7559   -1.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5579   -0.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1575   -1.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9559   -1.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5513   -1.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3548   -2.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5596   -2.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9618   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1630   -2.4966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5610   -1.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7625   -2.1609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3498   -1.5618    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2138    0.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389    0.5839    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0624   -1.5026    0.0000 O   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
  7  6  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 15 14  1  0
 10 15  2  0
 15 16  1  0
 16 17  1  0
 17  8  1  0
 17 18  2  0
 12 19  1  0
 20  7  1  0
 20  4  2  0
  3 21  1  0
 21 22  2  0
 23 21  1  0
 24 23  2  0
 24 25  1  0
 25  2  1  0
 26 25  2  0
 27 26  1  0
 28 27  2  0
 29 28  1  0
 29 30  1  0
 31 30  1  0
 31 32  2  0
 33 31  1  0
 34 33  1  0
 35 34  2  0
 23 35  1  0
 33 36  2  0
 36 28  1  0
 36 24  1  0
 37 30  1  0
 38 37  2  0
 38 39  1  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 42 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 47 46  1  0
 42 47  2  0
 47 48  1  0
 48 49  1  0
 49 40  1  0
 49 50  2  0
 44 51  1  0
 39 52  2  0
 53 52  1  0
 37 53  1  0
 29 54  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287280

   ---

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: 789.59

Molecular Weight (Monoisotopic): 787.9630

AlogP: 8.21

#Rotatable Bonds: 4

Polar Surface Area: 160.96

Molecular Species: NEUTRAL

HBA: 12

HBD: ┄

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.79

CX LogD: 7.79

Aromatic Rings: 8

Heavy Atoms: 54

QED Weighted: 0.13

Np Likeness Score: -0.58

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