Canadine (CHEM016600)

Record Information
Version1.0
Creation Date2016-05-22 03:38:10 UTC
Update Date2026-08-20 05:30:58 UTC
Accession NumberCHEM016600
Identification
Common NameCanadine
ClassSmall Molecule
Description
A berberine alkaloid that is 5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline substituted by methoxy groups at positions 9 and 10.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo(g)-1,3-benzodioxolo(5,6-a)quinolizineChEBI
5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo(g)benzo-1,3-dioxolo(5,6-a)quinolizineChEBI
9,10-Dimethoxy-2,3-(methylenedioxy)berbineChEBI
CanadinChEBI
TetrahydroberberineChEBI
XanthopuccineChEBI
Canadine, (+-)-isomerMeSH, HMDB
Canadine, (S)-isomerMeSH, HMDB
Canadine hydrochlorideMeSH, HMDB
Canadine, (R)-isomerMeSH, HMDB
Chemical FormulaC20H21NO4
Average Molecular Mass339.391 g/mol
Monoisotopic Mass339.147 g/mol
CAS Registry Number522-97-4
IUPAC Name16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-2,4(8),9,15,17,19-hexaene
Traditional Namecanadin
SMILESCOC1=CC=C2CC3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC
InChI IdentifierInChI=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
InChI KeyVZTUIEROBZXUFA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassProtoberberine alkaloids and derivatives
Sub ClassNot Available
Direct ParentProtoberberine alkaloids and derivatives
Alternative Parents
Substituents
  • Protoberberine skeleton
  • Tetrahydroprotoberberine skeleton
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Acetal
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
logP2.7ALOGPS
logP3.09ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.16 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.2 m³·mol⁻¹ChemAxon
Polarizability37.72 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0249579
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001827
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCanadine
Chemspider ID31709
ChEBI ID22998
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23747414
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24324259
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25093987