2-Pyridin-3-yl-9-aza-bicyclo[4.2.1]non-2-ene (DUB-165)

ID: ALA274538

PubChem CID: 44266824

Max Phase: Preclinical

Molecular Formula: C13H16N2

Molecular Weight: 200.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C1=C(c2cccnc2)C2CC[C@H](CC1)N2

Standard InChI:  InChI=1S/C13H16N2/c1-4-11-6-7-13(15-11)12(5-1)10-3-2-8-14-9-10/h2-3,5,8-9,11,13,15H,1,4,6-7H2/t11-,13?/m0/s1

Standard InChI Key:  BACMDOCEIHERJI-AMGKYWFPSA-N

Molfile:  

     RDKit          2D

 16 18  0  0  1  0  0  0  0  0999 V2000
    1.8667   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2125   -2.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -1.8625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792   -4.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -4.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750   -4.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7875   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0477   -4.8146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  1  2  0
  5  1  1  0
  6 11  2  0
  7  3  1  0
  8  2  1  0
  9  7  1  0
 10  4  1  0
 11  5  1  0
 12 15  2  0
 13  5  2  0
 10 14  1  0
 15 13  1  0
  8 14  1  0
  8  9  1  0
 12  6  1  0
  8 16  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA274538

   2-Pyridin-3-yl-9-aza-bicyclo[4.2.1]non-2-ene(DUB-165)

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: 200.28

Molecular Weight (Monoisotopic): 200.1313

AlogP: 2.38

#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: 10.28

CX LogP: 1.72

CX LogD: -1.00

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.75

Np Likeness Score: 0.91

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]

Source

Source(1):

• Scientific Literature