6,6'-dichloro-2,2'-bis(pyridin-2-ylmethyl)-9,9'-bipyrido[3,4-b]indole-2,2'-diium bromide

ID: ALA4240022

PubChem CID: 145983005

Max Phase: Preclinical

Molecular Formula: C34H24Br2Cl2N6

Molecular Weight: 587.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1ccc2c(c1)c1cc[n+](Cc3ccccn3)cc1n2-n1c2ccc(Cl)cc2c2cc[n+](Cc3ccccn3)cc21.[Br-].[Br-]

Standard InChI:  InChI=1S/C34H24Cl2N6.2BrH/c35-23-7-9-31-29(17-23)27-11-15-39(19-25-5-1-3-13-37-25)21-33(27)41(31)42-32-10-8-24(36)18-30(32)28-12-16-40(22-34(28)42)20-26-6-2-4-14-38-26;;/h1-18,21-22H,19-20H2;2*1H/q+2;;/p-2

Standard InChI Key:  XSRRODNZDAXENQ-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 44 49  0  0  0  0  0  0  0  0999 V2000
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    5.6213  -18.3538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0856  -18.0388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6369  -17.4303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3796  -16.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5771  -16.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542  -17.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2104  -17.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6609  -16.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8551  -16.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6016  -17.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1529  -18.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6227  -19.1751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2859  -19.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0325  -20.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5796  -21.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3802  -20.8712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6307  -20.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0819  -19.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4408  -17.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8117  -19.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9274  -21.4822    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3088  -16.0365    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.9902  -16.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5566  -19.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1083  -18.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8497  -17.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0450  -17.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4993  -18.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566  -18.9869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7925  -17.1570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3375  -16.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0832  -15.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2747  -15.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7290  -16.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6919  -18.7129    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3 10  1  0
  9  2  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  2 15  1  0
 15 17  1  0
 16 23  1  0
 22 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
  6 28  1  0
 19 29  1  0
 25 30  1  0
 12 31  1  0
 28 32  1  0
 29 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 33  1  0
 32 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 42 43  2  0
 43 32  1  0
M  CHG  4   1  -1   6   1  19   1  44  -1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 587.51

Molecular Weight (Monoisotopic): 586.1429

AlogP: 6.98

#Rotatable Bonds: 5

Polar Surface Area: 43.40

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 2.37

CX LogP: -2.65

CX LogD: -2.65

Aromatic Rings: 8

Heavy Atoms: 42

QED Weighted: 0.20

Np Likeness Score: -0.56

References

1. Suzuki K, Nomura I, Ninomiya M, Tanaka K, Koketsu M..  (2018)  Synthesis and antimicrobial activity of β-carboline derivatives with N2-alkyl modifications.,  28  (17): [PMID:30001916] [10.1016/j.bmcl.2018.06.050]

Source

Source(1):

• Scientific Literature