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CHEBI:16592 - (S)-canadine

ChEBI IDCHEBI:16592
ChEBI Name(S)-canadine
Stars
ASCII Name(S)-canadine
DefinitionThe (S)-enantiomer of canadine.
Secondary ChEBI IDsCHEBI:413, CHEBI:11059, CHEBI:11074, CHEBI:18773
Last Modified10 November 2016
DownloadsMolfile
FormulaC20H21NO4
Net Charge0
Average Mass339.391
Monoisotopic Mass339.14706
SMILES[H][C@@]12Cc3ccc(OC)c(OC)c3CN1CCc1cc3c(cc12)OCO3
InChIInChI=1S/C20H21NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3/t16-/m0/s1
InChIKeyVZTUIEROBZXUFA-INIZCTEOSA-N
Species of MetaboliteComponentSourceComments
Hydrastis canadensis (ncbitaxon:13569) leaf (BTO:0000713) PubMed (21661731) EtOH:H2O(50:50) extract of leaves
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.
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)
(S)-canadine (CHEBI:16592) has functional parent (S)-nandinine (CHEBI:132749)
(S)-canadine (CHEBI:16592) has role plant metabolite (CHEBI:76924)
(S)-canadine (CHEBI:16592) is a an (S)-7,8,13,14-tetrahydroprotoberberine (CHEBI:194528)
(S)-canadine (CHEBI:16592) is a canadine (CHEBI:22998)
(S)-canadine (CHEBI:16592) is enantiomer of (R)-canadine (CHEBI:18146)
Incoming Relation(s)
(S)-N-methylcanadine (CHEBI:16512) has functional parent (S)-canadine (CHEBI:16592)
(13S,14R)-1,13-dihydroxy-N-methylcanadine (CHEBI:141639) has functional parent (S)-canadine (CHEBI:16592)
(R)-canadine (CHEBI:18146) is enantiomer of (S)-canadine (CHEBI:16592)
IUPAC Name 
(13aS)-9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
Synonyms  Source
(S)-CanadineKEGG COMPOUND
(S)-TetrahydroberberineKEGG COMPOUND
(13aS)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizineKEGG COMPOUND
canadine l-formChemIDplus
UniProt Name  Source
(S)-canadineUniProt
Manual XrefsDatabases
C03329KEGG COMPOUND
C00028005KNApSAcK
Registry NumbersSources
Reaxys:96684Reaxys
CAS:5096-57-1KEGG COMPOUND
CAS:5096-57-1ChemIDplus
Citations