1,1'-((4,9-dibromo-1,3,6,8-tetraoxo-1,3,6,8-tetrahydrobenzo[lmn][3,8]phenanthroline-2,7-diyl)bis(ethane-2,1-diyl))bis(3-methyl-1H-imidazol-3-ium) Diiodide

ID: ALA5290404

Max Phase: Preclinical

Molecular Formula: C26H22Br2I2N6O4

Molecular Weight: 642.31

Names and Identifiers

Canonical SMILES:  C[n+]1ccn(CCN2C(=O)c3cc(Br)c4c5c(cc(Br)c(c35)C2=O)C(=O)N(CCn2cc[n+](C)c2)C4=O)c1.[I-].[I-]

Standard InChI:  InChI=1S/C26H22Br2N6O4.2HI/c1-29-3-5-31(13-29)7-9-33-23(35)15-11-18(28)22-20-16(12-17(27)21(19(15)20)25(33)37)24(36)34(26(22)38)10-8-32-6-4-30(2)14-32;;/h3-6,11-14H,7-10H2,1-2H3;2*1H/q+2;;/p-2

Standard InChI Key:  OOWDLWMGSZMQJC-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 40 43  0  0  0  0  0  0  0  0999 V2000
    5.2027   -0.4884    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114   -0.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3088   -0.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5204   -0.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9456   -0.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5425   -1.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2900   -1.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559   -2.1445    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7695   -0.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711    0.0330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7496    0.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9220    0.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4962    1.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3289    1.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    0.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    0.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9587   -0.0308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5364   -0.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9482   -1.4563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7855   -0.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1989    0.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0257    0.6851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4390    1.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2622    1.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3432    0.4123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5818    0.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0592   -0.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9710    1.4044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    2.1445    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1517    1.4617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979    0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4113    0.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2381    0.7491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6514    0.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4746    0.2189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5556    1.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7942    1.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0592   -0.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941   -1.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2832   -0.9491    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  2  2  0
  6  8  1  0
  5  9  1  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
  4 12  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
  3 15  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
  2 18  1  0
 18 19  2  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 23 22  1  0
 23 24  2  0
 24 25  1  0
 26 25  2  0
 22 26  1  0
 25 27  1  0
 16 28  2  0
 14 29  1  0
 11 30  2  0
 10 31  1  0
 31 32  1  0
 32 33  1  0
 34 33  1  0
 34 35  2  0
 35 36  1  0
 37 36  2  0
 33 37  1  0
 35 38  1  0
  9 39  2  0
M  CHG  4   1  -1  25   1  35   1  40  -1
M  END

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: 642.31

Molecular Weight (Monoisotopic): 640.0058

AlogP: 2.21

#Rotatable Bonds: 6

Polar Surface Area: 92.38

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -4.89

CX LogD: -4.89

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.24

Np Likeness Score: -0.20

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