1-(9-Aza-bicyclo[4.2.1]non-2-en-2-yl)-ethanone (Anatoxin-a)

ID: ALA25619

Cas Number: 85514-42-7

PubChem CID: 431734

Max Phase: Preclinical

Molecular Formula: C10H15NO

Molecular Weight: 165.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (+)-Anatoxin | Anatoxin-a|Anatoxin A|(+)-Anatoxin|CHEMBL25619|CHEBI:2706|85514-42-7|1-(9-azabicyclo[4.2.1]non-2-en-2-yl)ethanone|2-acetyl-9-azabicyclo[4.2.1]non-2-ene|Ethanone, 1-(9-azabicyclo(4.2.1)non-2-en-2-yl)-, (1R)-|1-(9-azabicyclo[4.2.1]non-4-en-5-yl)ethanone|AC1L8S0X|Anatoxin-A,(+)|C10841|SureCN160708|SCHEMBL160708|SGNXVBOIDPPRJJ-UHFFFAOYSA-N|DTXSID301338831|BDBM50023330|NCGC00162392-01|NCGC00162392-02|2-acetyl-9-azabicyclo [4.2.1]non-2-ene|1-(9-azabicyclo[4.2.1]non-2-en-2-yl)-ethanone|QShow More⌵

Canonical SMILES:  CC(=O)C1=CCCC2CCC1N2

Standard InChI:  InChI=1S/C10H15NO/c1-7(12)9-4-2-3-8-5-6-10(9)11-8/h4,8,10-11H,2-3,5-6H2,1H3

Standard InChI Key:  SGNXVBOIDPPRJJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 12 13  0  0  0  0  0  0  0  0999 V2000
   -0.5833   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1833   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583   -3.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3500   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1583   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208   -3.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -5.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -5.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417   -3.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  0
  5  1  2  0
  6  2  1  0
  7  4  2  0
  8  3  1  0
  9  6  1  0
 10  5  1  0
 11  4  1  0
 12 10  1  0
 12  8  1  0
  9  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA25619

   Ethanone, 1-(9-azabicyclo(4.2.1)non-2-en-2-yl)-, (1R)-

Molecule Features

Natural Product: Yes

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: 165.24

Molecular Weight (Monoisotopic): 165.1154

AlogP: 1.42

#Rotatable Bonds: 1

Polar Surface Area: 29.10

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.21

CX LogP: 1.19

CX LogD: -1.49

Aromatic Rings: ┄

Heavy Atoms: 12

QED Weighted: 0.64

Np Likeness Score: 2.13

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. Koskinen AM, Rapoport H..  (1985)  Synthetic and conformational studies on anatoxin-a: a potent acetylcholine agonist.,  28  (9): [PMID:4032432] [10.1021/jm00147a032]

3. Gohlke H, Schwarz S, Gündisch D, Tilotta MC, Weber A, Wegge T, Seitz G..  (2003)  3D QSAR analyses-guided rational design of novel ligands for the (alpha4)2(beta2)3 nicotinic acetylcholine receptor.,  46  (11): [PMID:12747776] [10.1021/jm020859m]

4. Wright E, Gallagher T, Sharples CG, Wonnacott S.  (1997)  Synthesis of UB-165: A novel nicotinic ligand and anatoxin-a/epibatidine hybrid,  7  (22): [10.1016/S0960-894X(97)10090-7]

5. 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]

6. Villeneuve G, Cécyre D, Lejeune H, Drouin M, Lan R, Quirion R..  (2003)  Rigidified acetylcholine mimics: conformational requirements for binding to neuronal nicotinic receptors.,  13  (21): [PMID:14552793] [10.1016/s0960-894x(03)00728-5]

7. Holladay MW, Dart MJ, Lynch JK..  (1997)  Neuronal nicotinic acetylcholine receptors as targets for drug discovery.,  40  (26): [PMID:9435889] [10.1021/jm970377o]

8. Kanne DB, Abood LG..  (1988)  Synthesis and biological characterization of pyridohomotropanes. Structure-activity relationships of conformationally restricted nicotinoids.,  31  (3): [PMID:3346870] [10.1021/jm00398a004]

9. PubChem BioAssay data set, 

10. Mazurov AA, Miao L, Bhatti BS, Strachan JP, Akireddy S, Murthy S, Kombo D, Xiao YD, Hammond P, Zhang J, Hauser TA, Jordan KG, Miller CH, Speake JD, Gatto GJ, Yohannes D..  (2012)  Discovery of 3-(5-chloro-2-furoyl)-3,7-diazabicyclo[3.3.0]octane (TC-6683, AZD1446), a novel highly selective α4β2 nicotinic acetylcholine receptor agonist for the treatment of cognitive disorders.,  55  (21): [PMID:22793665] [10.1021/jm3006542]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays