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

ID: ALA56296

PubChem CID: 10025698

Max Phase: Preclinical

Molecular Formula: C20H35IN2

Molecular Weight: 303.51

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H35N2.HI/c1-3-4-5-6-7-8-9-10-16-22-17-11-13-19(18-22)20-14-12-15-21(20)2;/h11,13,17-18,20H,3-10,12,14-16H2,1-2H3;1H/q+1;/p-1/t20-;/m0./s1

Standard InChI Key:  FCNGVUOMLWKVEV-BDQAORGHSA-M

Molfile:  

     RDKit          2D

 23 23  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
    1.1125   -6.4750    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
   -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
   -1.0208   -2.7667    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
  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 21  1  0
 18 22  1  0
 19 18  1  0
 20 19  1  0
 21 20  1  0
 22 15  1  0
 23 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: 303.51

Molecular Weight (Monoisotopic): 303.2795

AlogP: 4.88

#Rotatable Bonds: 10

Polar Surface Area: 7.12

Molecular Species: NEUTRAL

HBA: 1

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.64

CX LogP: 1.21

CX LogD: 0.77

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.44

Np Likeness Score: 0.31

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. Ayers JT, Dwoskin LP, Deaciuc AG, Grinevich VP, Zhu J, Crooks PA..  (2002)  bis-Azaaromatic quaternary ammonium analogues: ligands for alpha4beta2* and alpha7* subtypes of neuronal nicotinic receptors.,  12  (21): [PMID:12372503] [10.1016/s0960-894x(02)00687-x]

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