Structure via PubChem · Public domain (PubChem)
(-)-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.
Chemical data
- Formula
- C20H21NO4
- Molecular weight
- 339.4 g/mol
- IUPAC name
- (1S)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene
- SMILES
- COC1=C(C2=C(C[C@H]3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)OC
- InChIKey
- VZTUIEROBZXUFA-INIZCTEOSA-N
- XLogP
- 3.1
- Polar surface area
- 40.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 339.147058
Show 5 more facts
- chemical formula
- C₂₀H₂₁NO₄
- found in taxon
- Thalictrum flavum
- 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
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “(-)-canadine” article, available under the CC BY-SA 4.0 licence.