CHEBI:76923 - cyclanoline

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ChEBI Name cyclanoline
Definition A charged berberine alkaloid obtained by N-methylation of (S)-scoulerine.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter KAX
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Formula C20H24NO4
Net Charge +1
Average Mass 342.40830
Monoisotopic Mass 342.16998
InChI InChI=1S/C20H23NO4/c1-21-7-6-13-9-19(25-3)17(22)10-14(13)16(21)8-12-4-5-18(24-2)20(23)15(12)11-21/h4-5,9-10,16H,6-8,11H2,1-3H3,(H-,22,23)/p+1/t16-,21-/m0/s1
SMILES COc1ccc2C[C@H]3c4cc(O)c(OC)cc4CC[N@@+]3(C)Cc2c1O
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC (acetylcholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC, which helps breaking down of acetylcholine into choline and acetic acid.
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
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ChEBI Ontology
Outgoing cyclanoline (CHEBI:76923) has functional parent (S)-scoulerine (CHEBI:17129)
cyclanoline (CHEBI:76923) has role EC (acetylcholinesterase) inhibitor (CHEBI:38462)
cyclanoline (CHEBI:76923) has role plant metabolite (CHEBI:76924)
cyclanoline (CHEBI:76923) is a berberine alkaloid (CHEBI:22754)
cyclanoline (CHEBI:76923) is a quaternary ammonium ion (CHEBI:35267)
Synonyms Sources
(S)-cis-N-methylscoulerine UniProt
(S,S)-N-methylscoulerine ChEBI
Cissamine ChemIDplus
Manual Xrefs Databases
CN1500486 Patent
Cyclanoline Wikipedia
View more database links
Registry Numbers Types Sources
1555524 Reaxys Registry Number Reaxys
18556-27-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10726860 PubMed citation Europe PMC
14236247 PubMed citation Europe PMC
15802807 PubMed citation Europe PMC
16640839 PubMed citation Europe PMC
19624470 PubMed citation SUBMITTER
Last Modified
21 January 2014