1-Dodecyl-3-((S)-1-methyl-pyrrolidin-2-yl)-pyridinium iodide

ID: ALA55606

PubChem CID: 10321902

Max Phase: Preclinical

Molecular Formula: C22H39IN2

Molecular Weight: 331.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[I-]

Standard InChI:  InChI=1S/C22H39N2.HI/c1-3-4-5-6-7-8-9-10-11-12-18-24-19-13-15-21(20-24)22-16-14-17-23(22)2;/h13,15,19-20,22H,3-12,14,16-18H2,1-2H3;1H/q+1;/p-1/t22-;/m0./s1

Standard InChI Key:  RSLCPVZCHBQILE-FTBISJDPSA-M

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
    1.5792   -1.6792    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333   -0.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0125    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.5333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0125   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250    1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250    1.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458    0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6917    1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208   -1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -7.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -6.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125   -6.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -5.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -5.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -8.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  1  0
  4  5  1  0
  5  3  1  6
  6  2  2  0
  7  2  1  0
  8  2  1  0
  9  4  1  0
 10 13  1  0
 11  4  1  0
 12  5  1  0
 13  7  2  0
 14 12  1  0
 15  8  1  0
 16 17  1  0
 17 18  1  0
 18 24  1  0
 19 15  1  0
 20 19  1  0
 21 20  1  0
 22 21  1  0
 23 22  1  0
 24 23  1  0
 25 16  1  0
  3 10  2  0
  9 14  1  0
M  CHG  2   1  -1   2   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: 331.57

Molecular Weight (Monoisotopic): 331.3108

AlogP: 5.66

#Rotatable Bonds: 12

Polar Surface Area: 7.12

Molecular Species: NEUTRAL

HBA: 1

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.64

CX LogP: 2.10

CX LogD: 1.66

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.35

Np Likeness Score: 0.28

References

1. Crooks PA, Ayers JT, Xu R, Sumithran SP, Grinevich VP, Wilkins LH, Deaciuc AG, Allen DD, Dwoskin LP..  (2004)  Development of subtype-selective ligands as antagonists at nicotinic receptors mediating nicotine-evoked dopamine release.,  14  (8): [PMID:15050618] [10.1016/j.bmcl.2003.10.074]

2. Zheng F, McConnell MJ, Zhan CG, Dwoskin LP, Crooks PA..  (2009)  QSAR study on maximal inhibition (Imax) of quaternary ammonium antagonists for S-(-)-nicotine-evoked dopamine release from dopaminergic nerve terminals in rat striatum.,  17  (13): [PMID:19477134] [10.1016/j.bmc.2009.05.010]

3. Matera C, Pucci L, Fiorentini C, Fucile S, Missale C, Grazioso G, Clementi F, Zoli M, De Amici M, Gotti C, Dallanoce C..  (2015)  Bifunctional compounds targeting both D2 and non-α7 nACh receptors: design, synthesis and pharmacological characterization.,  101  [PMID:26164842] [10.1016/j.ejmech.2015.06.039]

Source

Source(1):

• Scientific Literature