1-[12-(2-amino-1-pyridiniumyl)dodecyl]-2-pyridiniumamine dibromide

ID: ALA74288

PubChem CID: 11329764

Max Phase: Preclinical

Molecular Formula: C22H36Br2N4

Molecular Weight: 356.56

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 1,12-Bis(2-Aminopyridinium)Dodecane Dibromide | CHEMBL74288|1,12-bis(2-aminopyridinium)dodecane dibromide

Canonical SMILES:  Nc1cccc[n+]1CCCCCCCCCCCC[n+]1ccccc1N.[Br-].[Br-]

Standard InChI:  InChI=1S/C22H34N4.2BrH/c23-21-15-9-13-19-25(21)17-11-7-5-3-1-2-4-6-8-12-18-26-20-14-10-16-22(26)24;;/h9-10,13-16,19-20,23-24H,1-8,11-12,17-18H2;2*1H

Standard InChI Key:  CYWFZWJPTAKSLA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 27  0  0  0  0  0  0  0  0999 V2000
    5.0500   -9.3625    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.5500   -6.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4042   -8.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6667   -8.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -7.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1292   -7.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5917   -9.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -6.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9292   -9.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125   -5.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4792   -8.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -7.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -6.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0625   -8.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2000   -5.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7417   -9.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -7.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -7.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750   -7.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -7.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -8.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -8.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2542   -8.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -6.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0167   -8.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -4.7125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  3  8  1  0
  4  2  1  0
  5  3  1  0
  6  4  1  0
  7  5  1  0
  8 15  1  0
  9  2  1  0
 10  3  2  0
 11  2  2  0
 12  5  2  0
 13  4  2  0
 14  9  1  0
 15 24  1  0
 16 11  1  0
 17 10  1  0
 18 25  1  0
 19 18  1  0
 20 19  1  0
 21 20  1  0
 22 21  1  0
 23 22  1  0
 24 23  1  0
 25 14  1  0
 26 16  2  0
 27 17  2  0
 13 26  1  0
 27 12  1  0
M  CHG  4   1  -1   2   1   3   1  28  -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: 356.56

Molecular Weight (Monoisotopic): 356.2929

AlogP: 4.03

#Rotatable Bonds: 13

Polar Surface Area: 59.80

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -3.89

CX LogD: -3.89

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.42

Np Likeness Score: -0.10

References

1. Ramström H, Bourotte M, Philippe C, Schmitt M, Haiech J, Bourguignon JJ..  (2004)  Heterocyclic bis-cations as starting hits for design of inhibitors of the bifunctional enzyme histidine-containing protein kinase/phosphatase from Bacillus subtilis.,  47  (9): [PMID:15084125] [10.1021/jm021043o]

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]

3. Calas M, Ouattara M, Piquet G, Ziora Z, Bordat Y, Ancelin ML, Escale R, Vial H..  (2007)  Potent antimalarial activity of 2-aminopyridinium salts, amidines, and guanidines.,  50  (25): [PMID:18004799] [10.1021/jm0704752]

Source

Source(1):

• Scientific Literature