CHEBI:16118 - berberine

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ChEBI Name berberine
ChEBI ID CHEBI:16118
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41098, CHEBI:13893, CHEBI:22753, CHEBI:3066
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Formula C20H18NO4
Net Charge +1
Average Mass 336.36126
Monoisotopic Mass 336.124
InChI InChI=1S/C20H18NO4/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/h3-4,7-10H,5-6,11H2,1-2H3/q+1
InChIKey YBHILYKTIRIUTE-UHFFFAOYSA-N
SMILES COc1ccc2cc3-c4cc5OCOc5cc4CC[n+]3cc2c1OC
Metabolite of Species Details
Hydrastis canadensis (NCBI:13569) Found in leaf (BTO:0000713). EtOH:H2O(50:50) extract of leaves See: PubMed
Coptis japonica (NCBI:3442) Found in rhizome (BTO:0001181). 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): potassium channel blocker
An agent that inhibits cell membrane glycoproteins that are selectively permeable to potassium ions.
EC 1.1.1.21 (aldehyde reductase) inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).
EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of 15-hydroxyprostaglandin dehydrogenase (NAD+) (EC 1.1.1.141).
EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor
An EC 1.13.11.* (oxidoreductase acting on single donors and incorporating 2 atoms of oxygen) inhibitor that interferes with the action of indoleamine 2,3-dioxygenase (EC 1.13.11.52).
EC 1.21.3.3 (reticuline oxidase) inhibitor
An EC 1.21.3.* (oxidoreductase acting on X-H and Y-H to form an X-Y bond, with oxygen as acceptor) inhibitor that interferes with the action of reticuline oxidase (EC 1.21.3.3, previously EC 1.5.3.9).
EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor
An EC 2.1.1.* (methyltransferases) inhibitor that interferes with the action of 3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase (EC 2.1.1.116).
EC 3.1.1.4 (phospholipase A2) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of phospholipase A2 (EC 3.1.1.4).
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
Any EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of prolyl oligopeptidase (EC 3.4.21.26).
EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor
An EC 3.4.14.* (dipeptidyl- and tripeptidyl-peptidases) inhibitor that specifically inhibits dipeptidyl peptidase-4 (EC 3.4.14.5).
EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
An EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor which interferes with the activity of the enzyme protein tyrosine phosphatases (PTPs), EC 3.1.3.48, involved in the removal of phosphate groups from phosphorylated tyrosine residues on proteins.
EC 3.1.1.7 (acetylcholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
EC 3.1.1.8 (cholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
EC 2.7.11.10 (IkappaB kinase) inhibitor
An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of IkappaB kinase (EC 2.7.11.10).
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor
An EC 2.1.1.* (methyltransferases) inhibitor that interferes with the action of (S)-tetrahydroprotoberberine N-methyltransferase (EC 2.1.1.122).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via botanical anti-fungal agent )
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via botanical anti-fungal agent )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via alkaloid antibiotic )
Application(s): antilipemic drug
A substance used to treat hyperlipidemia (an excess of lipids in the blood).
hypoglycemic agent
A drug which lowers the blood glucose level.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing berberine (CHEBI:16118) has role antilipemic drug (CHEBI:35679)
berberine (CHEBI:16118) has role antineoplastic agent (CHEBI:35610)
berberine (CHEBI:16118) has role antioxidant (CHEBI:22586)
berberine (CHEBI:16118) has role EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD+)] inhibitor (CHEBI:77108)
berberine (CHEBI:16118) has role EC 1.1.1.21 (aldehyde reductase) inhibitor (CHEBI:48550)
berberine (CHEBI:16118) has role EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor (CHEBI:72854)
berberine (CHEBI:16118) has role EC 1.21.3.3 (reticuline oxidase) inhibitor (CHEBI:77110)
berberine (CHEBI:16118) has role EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor (CHEBI:77111)
berberine (CHEBI:16118) has role EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor (CHEBI:77115)
berberine (CHEBI:16118) has role EC 2.7.11.10 (IκB kinase) inhibitor (CHEBI:77113)
berberine (CHEBI:16118) has role EC 3.1.1.4 (phospholipase A2) inhibitor (CHEBI:50469)
berberine (CHEBI:16118) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
berberine (CHEBI:16118) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
berberine (CHEBI:16118) has role EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor (CHEBI:35608)
berberine (CHEBI:16118) has role EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor (CHEBI:68612)
berberine (CHEBI:16118) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779)
berberine (CHEBI:16118) has role hypoglycemic agent (CHEBI:35526)
berberine (CHEBI:16118) has role metabolite (CHEBI:25212)
berberine (CHEBI:16118) has role potassium channel blocker (CHEBI:50509)
berberine (CHEBI:16118) is a alkaloid antibiotic (CHEBI:86322)
berberine (CHEBI:16118) is a berberine alkaloid (CHEBI:22754)
berberine (CHEBI:16118) is a botanical anti-fungal agent (CHEBI:86494)
berberine (CHEBI:16118) is a organic heteropentacyclic compound (CHEBI:38164)
IUPAC Name
9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium
Synonyms Sources
7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium IUPAC
9,10-dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbinium ChEBI
Berberin ChemIDplus
Berberine KEGG COMPOUND
BERBERINE PDBeChem
Umbellatine KEGG COMPOUND
Database Links Databases
BER PDBeChem
Berberine Wikipedia
C00001819 KNApSAcK
C00757 KEGG COMPOUND
DB04115 DrugBank
HMDB03409 HMDB
LSM-6553 LINCS
View more database links
Registry Numbers Types Sources
2086-83-1 CAS Registry Number KEGG COMPOUND
2086-83-1 CAS Registry Number NIST Chemistry WebBook
2086-83-1 CAS Registry Number ChemIDplus
3570374 Beilstein Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
25 February 2016