huperzine A (CHEBI:78330)

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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. It is also an effective inhibitor of acetylcholinesterase and has attracted interest as a therapeutic candidate for Alzheimer's disease.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C15H18N2O

Net Charge

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. nootropic agent Any compound that improves mental functions such as cognition, memory, intelligence, motivation, attention, and concentration.

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 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	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	Sources
(−)-huperazine A	ChemIDplus
(−)-selagine	ChemIDplus
(5R,9R,11E)-5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one	ChEBI
Hup A	ChemIDplus
HupA	ChEBI
huperzine-A	ChEBI
hupzine A	ChEBI
kimpukan A	ChemIDplus
selagine	ChemIDplus

Last Modified

09 September 2021