CHEBI:78330 - huperzine A

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ChEBI Name huperzine A
ChEBI ID CHEBI:78330
Definition A sesquiterpene alkaloid isolated from a club moss Huperzia serrata that has been shown to exhibit neuroprotective activity.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H18N2O
Net Charge 0
Average Mass 242.31620
Monoisotopic Mass 242.14191
InChI InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15+/m0/s1
InChIKey ZRJBHWIHUMBLCN-YQEJDHNASA-N
SMILES C\C=C1/[C@@H]2Cc3[nH]c(=O)ccc3[C@@]1(N)CC(C)=C2
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
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ChEBI Ontology
Outgoing huperzine A (CHEBI:78330) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
huperzine A (CHEBI:78330) has role neuroprotective agent (CHEBI:63726)
huperzine A (CHEBI:78330) has role plant metabolite (CHEBI:76924)
huperzine A (CHEBI:78330) is a organic heterotricyclic compound (CHEBI:26979)
huperzine A (CHEBI:78330) is a primary amino compound (CHEBI:50994)
huperzine A (CHEBI:78330) is a pyridone (CHEBI:38183)
huperzine A (CHEBI:78330) is a sesquiterpene alkaloid (CHEBI:26657)
IUPAC Name
(5R,9R,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one
Synonyms Sources
(−)-huperazine A ChemIDplus
(−)-selagine ChemIDplus
selagine ChemIDplus
Manual Xrefs Databases
DB04864 DrugBank
Huperzine_A Wikipedia
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Registry Numbers Types Sources
102518-79-6 CAS Registry Number ChemIDplus
3592896 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12895686 PubMed citation Europe PMC
23306162 PubMed citation Europe PMC
24129696 PubMed citation Europe PMC
24190328 PubMed citation Europe PMC
24299147 PubMed citation Europe PMC
24332448 PubMed citation Europe PMC
24639880 PubMed citation Europe PMC
Last Modified
07 May 2014