CHEBI:132893 - fangchinoline

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ChEBI Name fangchinoline
ChEBI ID CHEBI:132893
Definition A bisbenzylisoquinoline alkaloid that is (1β)- berbaman which has been substituted by methyl groups at the 2 and 2' positions, by methoxy groups at the 6, 6', and 12 positions, and by a hydroxy group at position 7. Isolated from Stephania tetrandra, it has been found to possess neuroprotective and anti-tumour activity.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter qingping liu
Supplier Information ZINC000038148193
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Fangchinoline is a chemical compound isolated from Stephania tetrandra. It has in vitro antiproliferative activity against a breast cancer cell line.
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Formula C37H40N2O6
Net Charge 0
Average Mass 608.725
Monoisotopic Mass 608.28864
InChI InChI=1S/C37H40N2O6/c1-38-14-12-24-19-31(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-32-18-23(8-11-30(32)41-3)17-29-35-25(13-15-39(29)2)20-34(43-5)36(40)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29-/m0/s1
InChIKey IIQSJHUEZBTSAT-VMPREFPWSA-N
SMILES O1C=2C=C3C(=CC2OC)CCN([C@H]3CC4=CC=C(OC=5C=C(C[C@@]6(N(CCC=7C6=C1C(O)=C(OC)C7)C)[H])C=CC5OC)C=C4)C
Metabolite of Species Details
Stephania tetrandra (NCBI:txid425106) Found in root (BTO:0001188). See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): anti-HIV-1 agent
An anti-HIV agent that destroys or inhibits the replication of HIV-1, the more infective and more virulent of the two types of HIV virus.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing fangchinoline (CHEBI:132893) has role anti-HIV-1 agent (CHEBI:64947)
fangchinoline (CHEBI:132893) has role anti-inflammatory agent (CHEBI:67079)
fangchinoline (CHEBI:132893) has role antineoplastic agent (CHEBI:35610)
fangchinoline (CHEBI:132893) has role antioxidant (CHEBI:22586)
fangchinoline (CHEBI:132893) has role neuroprotective agent (CHEBI:63726)
fangchinoline (CHEBI:132893) has role plant metabolite (CHEBI:76924)
fangchinoline (CHEBI:132893) is a aromatic ether (CHEBI:35618)
fangchinoline (CHEBI:132893) is a bisbenzylisoquinoline alkaloid (CHEBI:133004)
fangchinoline (CHEBI:132893) is a macrocycle (CHEBI:51026)
IUPAC Name
(1β)-6,6',12-trimethoxy-2,2'-dimethylberbaman-7-ol
Synonyms Sources
(+)-fangchinoline ChemIDplus
(+)-limacine ChemIDplus
(1β)-2,2'-dimethyl-6,6',12-trimethoxyberbaman-7-ol ChemIDplus
7-O-demethyltetrandrine ChemIDplus
Manual Xref Database
Fangchinoline Wikipedia
View more database links
Registry Numbers Types Sources
436-77-1 CAS Registry Number ChemIDplus
78975 Reaxys Registry Number Reaxys
Citations Waiting for Citations
Last Modified
22 August 2016