ContaminantDB: Canadine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:38:10 UTC

Update Date

2016-11-09 01:15:26 UTC

Accession Number

CHEM016600

Identification

Common Name

Canadine

Class

Small 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 Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo(g)-1,3-benzodioxolo(5,6-a)quinolizine	ChEBI
5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo(g)benzo-1,3-dioxolo(5,6-a)quinolizine	ChEBI
9,10-Dimethoxy-2,3-(methylenedioxy)berbine	ChEBI
Canadin	ChEBI
Tetrahydroberberine	ChEBI
Xanthopuccine	ChEBI
Canadine, (+-)-isomer	MeSH, HMDB
Canadine, (S)-isomer	MeSH, HMDB
Canadine hydrochloride	MeSH, HMDB
Canadine, (R)-isomer	MeSH, HMDB

Chemical Formula

C₂₀H₂₁NO₄

Average Molecular Mass

339.391 g/mol

Monoisotopic Mass

339.147 g/mol

CAS Registry Number

522-97-4

IUPAC Name

16,17-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 Name

canadin

SMILES

COC1=CC=C2CC3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC

InChI Identifier

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

InChI Key

VZTUIEROBZXUFA-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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:22998 )
organic heteropentacyclic compound (CHEBI:22998 )
berberine alkaloid (CHEBI:22998 )
oxacycle (CHEBI:22998 )
a small molecule (S-TETRAHYDROBERBERINE )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.05 g/L	ALOGPS
logP	2.7	ALOGPS
logP	3.09	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.2 m³·mol⁻¹	ChemAxon
Polarizability	37.72 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ds-0936000000-2ef2ecf5b59bb80983c2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0900000000-3534c40094334e877b54	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004l-0904000000-2d53313907439723e6e3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0209000000-cc5ab71e8b9121723a26	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-f31964750248780eb770	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0019000000-c6398143436d0b8283dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-0690000000-b2b45f4e103d82fb14fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-fe3a00a1a08d036b48d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0019000000-cee6687b274772151a2d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-0392000000-b5772255a7ead50853d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-952964009ca467e58825	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0009000000-e828629c20a2db682012	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0946000000-079dd7d3d8a3d7c8e15a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-a9f00908271fb71883c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-0009000000-3ed8d3569e862d52f044	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-007c-0195000000-a9539962a59de76ca561	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0249579

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001827

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Canadine

Chemspider ID

31709

ChEBI ID

22998

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not 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

Canadine (CHEM016600)

Structure for CHEM016600: Canadine