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CHEBI:76923 - cyclanoline

ChEBI IDCHEBI:76923
ChEBI Namecyclanoline
Stars
DefinitionA charged berberine alkaloid obtained by N-methylation of (S)-scoulerine.
Last Modified21 January 2014
SubmitterKAX
DownloadsMolfile
FormulaC20H24NO4
Net Charge+1
Average Mass342.415
Monoisotopic Mass342.16998
SMILES[H][C@@]12Cc3ccc(OC)c(O)c3C[N@+]1(C)CCc1cc(OC)c(O)cc12
InChIInChI=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
InChIKeyLKLWVKCEYSPQHL-KKSFZXQISA-O
Wikipedia
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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.
ChEBI Ontology
Outgoing Relation(s)
cyclanoline (CHEBI:76923) has functional parent (S)-scoulerine (CHEBI:17129)
cyclanoline (CHEBI:76923) has role EC 3.1.1.7 (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)
IUPAC Name 
(7S,13aS)-2,9-dihydroxy-3,10-dimethoxy-7-methyl-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolinium
Synonyms  Source
CissamineChemIDplus
(S,S)-N-methylscoulerineChEBI
UniProt Name  Source
(S)-cis-N-methylscoulerineUniProt
Manual XrefsDatabases
CyclanolineWikipedia
CN1500486Patent
Registry NumbersSources
Reaxys:1555524Reaxys
CAS:18556-27-9ChemIDplus
Citations