(-)-canadine
Sign in to saveAlso known as canadine l-form, alpha-canadine, (13aS)-9,10-dimethoxy-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
Canadine, also known as '(S)-tetrahydroberberine and xanthopuccine', is a benzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup, and is present in many plants from the family Papaveraceae, such as Corydalis yanhusuo and C. turtschaninovii.
Wikidata facts
- Mass
- 339.147058
Show 4 more facts
- chemical formula
- C₂₀H₂₁NO₄
- isomeric SMILES
- COC1=C(C2=C(C[C@H]3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)OC
- canonical SMILES
- COC1=C(C2=C(CC3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)OC
- Commons category
- Canadine
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Article
4 sectionsContents
- Biosynthesis
- Effects
- [[CPU 86017]]
- References
Canadine, also known as '(S)-tetrahydroberberine and xanthopuccine', is a benzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup, and is present in many plants from the family Papaveraceae, such as Corydalis yanhusuo and C. turtschaninovii.
==Biosynthesis== Metabolically, (S)-canadine is derived from (S)-reticuline, a pivotal intermediate in the biosynthesis of numerous BIA structural subgroups, through three enzymatic steps: 1) berberine bridge enzyme to (S)-scoulerine; 2) (S)-scoulerine 9-O-methyltransferase to (S)-tetrahydrocolumbamine; and 3) (S)-canadine synthase/CYP719A21 to (S)-canadine.