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CHEBI:66604 - lycoperine A

ChEBI IDCHEBI:66604
ChEBI Namelycoperine A
Stars
DefinitionAn alkaloid that consists of piperidine substituted by [1-acetyl-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinolin-5-yl]methyl moieties at positions 2 and 6 respectively. Isolated from Lycopodium hamiltonii, it exhibits acetylcholinesterase inhibitory activity.
Last Modified26 March 2013
DownloadsMolfile
FormulaC31H49N3O2
Net Charge0
Average Mass495.752
Monoisotopic Mass495.38248
SMILES[H][C@]12C[C@@H](C)CC(C[C@H]3CCC[C@@H](CC4=C5CCCN(C(C)=O)[C@@]5([H])C[C@@H](C)C4)N3)=C1CCCN2C(C)=O
InChIInChI=1S/C31H49N3O2/c1-20-14-24(28-10-6-12-33(22(3)35)30(28)16-20)18-26-8-5-9-27(32-26)19-25-15-21(2)17-31-29(25)11-7-13-34(31)23(4)36/h20-21,26-27,30-32H,5-19H2,1-4H3/t20-,21-,26-,27+,30-,31-/m0/s1
InChIKeyWDJDPNAURLPQIO-QDLVWTCJSA-N
Species of MetaboliteComponentSourceComments
Lycopodium hamiltonii (ncbitaxon:3251) - PubMed (16381583)
Roles Classification
Biological Roles:
EC 3.1.1.7 (acetylcholinesterase) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
lycoperine A (CHEBI:66604) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
lycoperine A (CHEBI:66604) has role metabolite (CHEBI:25212)
lycoperine A (CHEBI:66604) is a acetamides (CHEBI:22160)
lycoperine A (CHEBI:66604) is a alkaloid (CHEBI:22315)
lycoperine A (CHEBI:66604) is a isoquinolines (CHEBI:24922)
lycoperine A (CHEBI:66604) is a piperidines (CHEBI:26151)
IUPAC Name 
1,1'-[(2R,6S)-piperidine-2,6-diylbis{methanediyl[(7S,8aS)-7-methyl-3,4,6,7,8,8a-hexahydroquinoline-5,1(2H)-diyl]}]diethanone
Synonym  Source
(−)-lycoperine AChEBI
Registry NumbersSources
Reaxys:19931970Reaxys
Citations