1,12-bis(4-N,N-dimethylaminopyridinium)dodecane dibromide

ID: ALA228000

Cas Number: 936498-64-5

PubChem CID: 44423477

Max Phase: Preclinical

Molecular Formula: C26H44Br2N4

Molecular Weight: 412.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1cc[n+](CCCCCCCCCCCC[n+]2ccc(N(C)C)cc2)cc1.[Br-].[Br-]

Standard InChI:  InChI=1S/C26H44N4.2BrH/c1-27(2)25-15-21-29(22-16-25)19-13-11-9-7-5-6-8-10-12-14-20-30-23-17-26(18-24-30)28(3)4;;/h15-18,21-24H,5-14,19-20H2,1-4H3;2*1H/q+2;;/p-2

Standard InChI Key:  SRYRXSJEWKGQSC-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 32 31  0  0  0  0  0  0  0  0999 V2000
    5.6875   -7.3125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7973   -9.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7984  -10.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836  -10.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3672  -10.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700   -9.1963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0854   -8.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571   -8.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0589   -9.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7718   -8.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878   -9.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2008   -8.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9168   -9.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6297   -8.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3457   -9.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0586   -8.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5132  -10.4393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7746   -9.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4875   -8.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2036   -9.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9165   -8.7488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6295   -9.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3420   -8.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3393   -7.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6183   -7.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9088   -7.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0517   -7.5034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7682   -7.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5139  -11.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2274  -10.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0475   -6.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1562   -7.2500    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  4  5  2  0
  3 17  1  0
  8  9  1  0
 16 18  1  0
 18 19  1  0
  9 10  1  0
 19 20  1  0
  5  6  1  0
 20 21  1  0
 10 11  1  0
 21 22  2  0
  3  4  1  0
 22 23  1  0
 11 12  1  0
 23 24  2  0
  6  7  2  0
 24 25  1  0
 12 13  1  0
 25 26  2  0
 26 21  1  0
  7  2  1  0
 24 27  1  0
 13 14  1  0
 27 28  1  0
  2  3  2  0
 17 29  1  0
 14 15  1  0
 17 30  1  0
  6  8  1  0
 27 31  1  0
M  CHG  4   1  -1   6   1  21   1  32  -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: 412.67

Molecular Weight (Monoisotopic): 412.3555

AlogP: 4.99

#Rotatable Bonds: 15

Polar Surface Area: 14.24

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.43

CX LogP: -2.20

CX LogD: -2.20

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.30

Np Likeness Score: -0.24

References

1. 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]

2. Trousil S, Carroll L, Kalusa A, Aberg O, Kaliszczak M, Aboagye EO..  (2013)  Design of symmetrical and nonsymmetrical N,N-dimethylaminopyridine derivatives as highly potent choline kinase alpha inhibitors.,  4  (4): [PMID:24976941] [10.1039/c3md00068k]

Source

Source(1):

• Scientific Literature