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CHEBI:78330 - huperzine A

ChEBI IDCHEBI:78330
ChEBI Namehuperzine A
Stars
DefinitionA sesquiterpene alkaloid isolated from a club moss Huperzia serrata that has been shown to exhibit neuroprotective activity. It is also an effective inhibitor of acetylcholinesterase and has attracted interest as a therapeutic candidate for Alzheimer's disease.
Last Modified9 September 2021
Submitternamrata
DownloadsMolfile
FormulaC15H18N2O
Net Charge0
Average Mass242.322
Monoisotopic Mass242.14191
SMILES[H][C@@]12C=C(C)C[C@@](N)(/C1=C/C)c1ccc(=O)nc1C2
InChIInChI=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
InChIKeyZRJBHWIHUMBLCN-YQEJDHNASA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Huperzia serrata (ncbitaxon:355589) - PubMed (34072855)
Huperzia selago (ncbitaxon:70001) - PubMed (32708929)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
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.
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.
Applications:
nootropic agent  Any compound that improves mental functions such as cognition, memory, intelligence, motivation, attention, and concentration.
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
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 nootropic agent (CHEBI:66980)
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)
huperzine A (CHEBI:78330) is conjugate base of huperzine A(1+) (CHEBI:178022)
Incoming Relation(s)
huperzine A(1+) (CHEBI:178022) is conjugate acid of huperzine A (CHEBI:78330)
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  Source
(−)-selagineChemIDplus
(−)-huperazine AChemIDplus
selagineChemIDplus
Hup AChemIDplus
hupzine AChEBI
kimpukan AChemIDplus
Manual XrefsDatabases
Huperzine_AWikipedia
DB04864DrugBank
C00028361KNApSAcK
HMDB0242654HMDB
16736021ChemSpider
Registry NumbersSources
Reaxys:3592896Reaxys
CAS:102518-79-6ChemIDplus
Citations