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CHEBI:16118 - berberine
| Formula | C20H18NO4 |
| Net Charge | +1 |
| Average Mass | 336.367 |
| Monoisotopic Mass | 336.12303 |
| SMILES | COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2 |
| 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 |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Coptis japonica (ncbitaxon:3442) | rhizome (BTO:0001181) | PubMed (21401114) | |
| Hydrastis canadensis (ncbitaxon:13569) | leaf (BTO:0000713) | PubMed (21661731) | EtOH:H2O(50:50) extract of leaves |
| Homo sapiens (ncbitaxon:9606) | blood plasma (BTO:0000118) | PubMed (17531424) |
| Roles Classification |
|---|
| Chemical Role: | antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. |
| Biological Roles: | 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 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 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 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). potassium channel blocker An agent that inhibits cell membrane glycoproteins that are selectively permeable to potassium ions. 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 3.1.3.48 (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 3.1.1.8 (cholinesterase) inhibitor An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8). metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. EC 2.7.11.10 (IkappaB kinase) inhibitor An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of IκB kinase (EC 2.7.11.10). 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 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 1.21.3.3 (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 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 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). antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. |
| Applications: | geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. hypoglycemic agent A drug which lowers the blood glucose level. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. antilipemic drug A substance used to treat hyperlipidemia (an excess of lipids in the blood). |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| 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 geroprotector (CHEBI:176497) |
| 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 | Source |
|---|---|
| Berberine | KEGG COMPOUND |
| Umbellatine | KEGG COMPOUND |
| 9,10-dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbinium | ChEBI |
| 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium | IUPAC |
| Berberin | ChemIDplus |
| BERBERINE | PDBeChem |
| UniProt Name | Source |
|---|---|
| berberine | UniProt |
| Citations |
|---|