16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2(10),3,8,15,17,19-hexaene

• ChemBase ID: 163572
• Molecular Formular: C20H21NO4
• Molecular Mass: 339.38504
• Monoisotopic Mass: 339.14705816
• SMILES: c1c(c(c2c(c1)CC1N(C2)CCc2c1cc1c(c2)OCO1)OC)OC
• Canonical SMILES: COc1c(OC)ccc2c1CN1CCc3c(C1C2)cc1c(c3)OCO1
• InChI: 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
• InChIKey: VZTUIEROBZXUFA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^2,^1^0.0^4,^8.0^1^5,^2^0]henicosa-2(10),3,8,15,17,19-hexaene; 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^2,^1^0.0^4,^8.0^1^5,^2^0]henicosa-2,4(8),9,15(20),16,18-hexaene
• IUPAC Traditional name: 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^2,^1^0.0^4,^8.0^1^5,^2^0]henicosa-2(10),3,8,15,17,19-hexaene; canadin
• Synonyms: 5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine; 9-Deoxy-16,17-dihydroberberine; 9,10-Dimethoxy-2,3-(methylenedioxy)berbine; (±)-Canadine; (±)-Tetrahydroberberine; Tetrahydroberberine,; NSC 36351; NSC 94918; Tetrahydroberberine; Tetrahydroumbellatine; Xanthopuccine; dl-Canadine; dl-Tetrahydroberberine; Canadine

Database IDs

• CAS Number: 522-97-4
• PubChem SID: 162257707
• PubChem CID: 34458

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.7994096
• LogD (pH = 7.4): 3.081456
• Log P: 3.0865507
• Molar Refractivity: 94.196 cm^3
• Polarizability: 36.53476 Å^3
• Polar Surface Area: 40.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Description: Racemic
• Classification: Genuine Natural Compounds

DETAILS

Toronto Research Chemicals - C175175

Canadine is a protoberberine alkaloid which potently block functional KATP channels natively expressed on midbrain dopamine neurons. Canadine is used for treatment of degenerative diseases or conditions associated with KATP channel signaling.

REFERENCES

• Duchowicz, P., et al.: Bioorg. Med. Chem., 14, 5876 (2006)
• Sun., et al.: Br. J. Pharmcol., 158, 1302 (2006)
• Deeb, O., et al.: Chem. Biol. Drug Des., 76, 255 (2006)