1-[6-(4-iminiopyridin-1(4H)-yl)dodecylpyridin-4(1H)-iminium dibromide

ID: ALA32222

PubChem CID: 13408453

Max Phase: Preclinical

Molecular Formula: C22H36Br2N4

Molecular Weight: 354.54

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 1,12-Bis(4-Aminopyridinium)Dodecane Dibromide | CHEMBL32222|1,12-bis(4-aminopyridinium)dodecane dibromide

Canonical SMILES:  Br.Br.N=c1ccn(CCCCCCCCCCCCn2ccc(=N)cc2)cc1

Standard InChI:  InChI=1S/C22H34N4.2BrH/c23-21-11-17-25(18-12-21)15-9-7-5-3-1-2-4-6-8-10-16-26-19-13-22(24)14-20-26;;/h11-14,17-20,23-24H,1-10,15-16H2;2*1H

Standard InChI Key:  QXKBSWAARYHOJE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 27  0  0  0  0  0  0  0  0999 V2000
   -2.1500   -1.5125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.5750   -5.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -2.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3750   -5.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -1.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4750   -4.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4667   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7750   -5.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8667   -4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8750   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9750   -5.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6750   -4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -3.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0750   -4.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -2.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -3.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -3.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2250   -5.8042    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  3 16  1  0
  4 10  2  0
  5 11  2  0
  6 15  2  0
  7 12  2  0
  8 13  2  0
  9 14  2  0
 10  9  1  0
 11  6  1  0
 12  2  1  0
 13  3  1  0
 14  2  1  0
 15  3  1  0
 16 19  1  0
 17  2  1  0
 18 17  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 18  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 20  1  0
 10  7  1  0
 11  8  1  0
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: 354.54

Molecular Weight (Monoisotopic): 354.2783

AlogP: 4.85

#Rotatable Bonds: 13

Polar Surface Area: 57.56

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 12.43

CX LogP: 5.30

CX LogD: -1.49

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.48

Np Likeness Score: -0.22

References

1. Bailey DM, DeGrazia CG, Hoff SJ, Schulenberg PL, O'Connor JR, Paris DA, Slee AM..  (1984)  Bispyridinamines: a new class of topical antimicrobial agents as inhibitors of dental plaque.,  27  (11): [PMID:6492075] [10.1021/jm00377a014]

2. Ng CK, Singhal V, Widmer F, Wright LC, Sorrell TC, Jolliffe KA..  (2007)  Synthesis, antifungal and haemolytic activity of a series of bis(pyridinium)alkanes.,  15  (10): [PMID:17383187] [10.1016/j.bmc.2007.03.018]

Source

Source(1):

• Scientific Literature