(S)-3-(Azetidin-2-ylmethoxy)-5-(hex-1-ynyl)-2-methylpyridine

ID: ALA2323566

PubChem CID: 71525308

Max Phase: Preclinical

Molecular Formula: C16H22N2O

Molecular Weight: 258.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC#Cc1cnc(C)c(OC[C@@H]2CCN2)c1

Standard InChI:  InChI=1S/C16H22N2O/c1-3-4-5-6-7-14-10-16(13(2)18-11-14)19-12-15-8-9-17-15/h10-11,15,17H,3-5,8-9,12H2,1-2H3/t15-/m0/s1

Standard InChI Key:  TVQVEBXIMQEOQV-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  1  0  0  0  0  0999 V2000
    8.8379   -2.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7983   -3.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4985   -2.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1983   -3.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8985   -2.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2368   -5.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6857   -4.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2974   -3.3429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  3  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  6
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 15  1  0
 12 19  2  0
 19  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2323566

   3-[[(2S)-azetidin-2-yl]methoxy]-5-hex-1-ynyl-2-methylpyridine

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: 258.36

Molecular Weight (Monoisotopic): 258.1732

AlogP: 2.67

#Rotatable Bonds: 5

Polar Surface Area: 34.15

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.79

CX LogP: 2.63

CX LogD: 0.30

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.65

Np Likeness Score: 0.02

References

1. Liu Y, Richardson J, Tran T, Al-Muhtasib N, Xie T, Yenugonda VM, Sexton HG, Rezvani AH, Levin ED, Sahibzada N, Kellar KJ, Brown ML, Xiao Y, Paige M..  (2013)  Chemistry and pharmacological studies of 3-alkoxy-2,5-disubstituted-pyridinyl compounds as novel selective α4β2 nicotinic acetylcholine receptor ligands that reduce alcohol intake in rats.,  56  (7): [PMID:23540678] [10.1021/jm4000374]

2.  (2016)  2,5-disubstituted-pyridyl nicotinic ligands, and methods of use thereof, 

Source

Source(2):

• Scientific Literature
• BindingDB Database