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CHEBI:65660 - corynoline

ChEBI IDCHEBI:65660
ChEBI Namecorynoline
Stars
DefinitionA benzophenanthridine alkaloid that is chelidonine substituted by a methyl group at position 13. Isolated from the aerial parts of Corydalis incisa, it acts as an acetylcholinesterase inhibitor and also exhibits antineoplastic and hepatoprotective activity.
Last Modified14 December 2012
DownloadsMolfile
FormulaC21H21NO5
Net Charge0
Average Mass367.401
Monoisotopic Mass367.14197
SMILES[H][C@@]12c3cc4c(cc3C[C@H](O)[C@]1(C)c1ccc3c(c1CN2C)OCO3)OCO4
InChIInChI=1S/C21H21NO5/c1-21-14-3-4-15-19(27-10-24-15)13(14)8-22(2)20(21)12-7-17-16(25-9-26-17)5-11(12)6-18(21)23/h3-5,7,18,20,23H,6,8-10H2,1-2H3/t18-,20+,21-/m0/s1
InChIKeyIQUGPRHKZNCHGC-TYPHKJRUSA-N
Species of MetaboliteComponentSourceComments
Corydalis incisa (ncbitaxon:404570) aerial part (BTO:0001658) PubMed (17366734)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
Applications:
hepatoprotective agent  Any compound that is able to prevent damage to the liver.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
corynoline (CHEBI:65660) has functional parent chelidonine (CHEBI:31389)
corynoline (CHEBI:65660) has role antineoplastic agent (CHEBI:35610)
corynoline (CHEBI:65660) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
corynoline (CHEBI:65660) has role hepatoprotective agent (CHEBI:62868)
corynoline (CHEBI:65660) has role metabolite (CHEBI:25212)
corynoline (CHEBI:65660) is a benzophenanthridine alkaloid (CHEBI:38517)
corynoline (CHEBI:65660) is a cyclic acetal (CHEBI:59770)
corynoline (CHEBI:65660) is a isoquinolines (CHEBI:24922)
corynoline (CHEBI:65660) is a organic heterohexacyclic compound (CHEBI:51914)
corynoline (CHEBI:65660) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
13-methylchelidonine
Synonyms  Source
(+)-corynolineChEBI
(5bR,6S,12bR)-5b,13-dimethyl-5b,6,7,12b,13,14-hexahydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-6-olChEBI
(11S,13R,14R)-corynolineChEBI
Registry NumbersSources
Reaxys:4275687Reaxys
CAS:18797-79-0ChemIDplus
Citations