2-(6-Chloro-pyridin-3-yl)-9-aza-bicyclo[4.2.1]non-2-ene (UB-165)

ID: ALA275466

PubChem CID: 44266835

Max Phase: Preclinical

Molecular Formula: C13H15ClN2

Molecular Weight: 234.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1ccc(C2=CCC[C@H]3CCC2N3)cn1

Standard InChI:  InChI=1S/C13H15ClN2/c14-13-7-4-9(8-15-13)11-3-1-2-10-5-6-12(11)16-10/h3-4,7-8,10,12,16H,1-2,5-6H2/t10-,12?/m0/s1

Standard InChI Key:  TVSNVPGPFGAKPT-NUHJPDEHSA-N

Molfile:  

     RDKit          2D

 17 19  0  0  1  0  0  0  0  0999 V2000
    9.2750   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6167   -2.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7500   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3500   -1.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4750   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8750   -1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6417   -3.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1542   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2125   -3.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9917   -2.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -3.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1917   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0750   -1.3667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.9875   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5000   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9792   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4497   -4.8728    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  8  2  0
  5  1  1  0
  6 12  2  0
  7  1  2  0
  8  5  1  0
  9  3  1  0
 10  5  2  0
 11  2  1  0
 12 10  1  0
 13  6  1  0
 14  9  1  0
 15  7  1  0
 15 16  1  0
 11 16  1  0
 11 14  1  0
  6  4  1  0
 11 17  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA275466

   (6S)-2-(6-chloropyridin-3-yl)-9-azabicyclo[4.2.1]non-2-ene

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: 234.73

Molecular Weight (Monoisotopic): 234.0924

AlogP: 3.03

#Rotatable Bonds: 1

Polar Surface Area: 24.92

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.25

CX LogP: 2.54

CX LogD: -0.16

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.76

Np Likeness Score: 0.72

References

1. Gohlke H, Gündisch D, Schwarz S, Seitz G, Tilotta MC, Wegge T..  (2002)  Synthesis and nicotinic binding studies on enantiopure diazine analogues of the novel (2-chloro-5-pyridyl)-9-azabicyclo[4.2.1]non-2-ene UB-165.,  45  (5): [PMID:11855986] [10.1021/jm010936y]

2. Sharples CG, Karig G, Simpson GL, Spencer JA, Wright E, Millar NS, Wonnacott S, Gallagher T..  (2002)  Synthesis and pharmacological characterization of novel analogues of the nicotinic acetylcholine receptor agonist (+/-)-UB-165.,  45  (15): [PMID:12109907] [10.1021/jm020814l]

3. Jensen AA, Frølund B, Liljefors T, Krogsgaard-Larsen P..  (2005)  Neuronal nicotinic acetylcholine receptors: structural revelations, target identifications, and therapeutic inspirations.,  48  (15): [PMID:16033252] [10.1021/jm040219e]

Source

Source(1):

• Scientific Literature