(R)-Canadine
PubChem CID
443422
Structure
Molecular Formula
Synonyms
- (R)-(+)-Canadine
- (R)-Canadine
- 2086-96-6
- (+)-Tetrahydroberberine
- (+)-Canadine
Molecular Weight
339.4 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
- Create:2004-09-16
- Modify:2025-01-18
Description
(R)-canadine is a canadine which has R configuration. It is an enantiomer of a (S)-canadine.
(R)-Canadine has been reported in Hydrastis canadensis, Corydalis solida, and other organisms with data available.
Chemical Structure Depiction
(1R)-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
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)
InChI=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-/m1/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)
VZTUIEROBZXUFA-MRXNPFEDSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)
COC1=C(C2=C(C[C@@H]3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)OC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C20H21NO4
Computed by PubChem 2.2 (PubChem release 2024.11.20)
34174-53-3
- canadine
- canadine hydrochloride
- canadine, (+-)-isomer
- canadine, (R)-isomer
- canadine, (S)-isomer
- tetrahydroberberine
- (R)-(+)-Canadine
- (R)-Canadine
- 2086-96-6
- (+)-Tetrahydroberberine
- (+)-Canadine
- Canadine, (+)-
- Canadine d-form [MI]
- (R)-(+)-Tetrahydroberberine
- CHEMBL476501
- MB5J6D245F
- CHEBI:18146
- (1R)-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
- (13aR)-9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
- 6H-Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (13aR)-
- beta-Canadine
- NCGC00016486-01
- CAS-522-97-4
- .BETA.-CANADINE
- canadine, (+-)-isomer
- (R)-(+)-Canadine
- UNII-MB5J6D245F
- MLS002473083
- SCHEMBL14184002
- HY-N1418A
- DTXSID301313477
- HMS2213J07
- BDBM50429049
- AKOS037514859
- DA-69179
- SMR001397186
- CS-0133285
- Q27102853
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
339.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
3.1
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
339.14705815 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
339.14705815 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
40.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
25
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
488
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Calcium Channel Blockers
A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)
Anti-Arrhythmia Agents
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)
Platelet Aggregation Inhibitors
Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=VZTUIEROBZXUFA-MRXNPFEDSA-N
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/(+)-Tetrahydroberberinehttps://commonchemistry.cas.org/detail?cas_rn=2086-96-6
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSTox(+)-Tetrahydroberberinehttps://comptox.epa.gov/dashboard/DTXSID301313477CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- ChEBI
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/(R)-Canadinehttps://www.wikidata.org/wiki/Q27102853LOTUS Treehttps://lotus.naturalproducts.net/
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- Drug Gene Interaction database (DGIdb)LICENSEThe data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.http://www.dgidb.org/downloadsCHEMBL:CHEMBL476501https://www.dgidb.org/drugs/chembl:CHEMBL476501
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlPhytochemical compoundshttp://www.genome.jp/kegg-bin/get_htext?br08003.keg
- Natural Product Activity and Species Source (NPASS)
- Metabolomics Workbench
- Rhea - Annotated Reactions DatabaseLICENSERhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.https://www.rhea-db.org/help/license-disclaimer
- Wikidata(+)-canadinehttps://www.wikidata.org/wiki/Q27102853
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlCalcium Channel Blockershttps://www.ncbi.nlm.nih.gov/mesh/68002121Anti-Arrhythmia Agentshttps://www.ncbi.nlm.nih.gov/mesh/68000889Platelet Aggregation Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68010975
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 402546683https://pubchem.ncbi.nlm.nih.gov/substance/402546683
CONTENTS