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CHEBI:3092 - bicuculline
| ChEBI ID | CHEBI:3092 |
| ChEBI Name | bicuculline |
| Stars | |
| Definition | A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species. |
| Last Modified | 26 November 2019 |
| Downloads |
| Formula | C20H17NO6 |
| Net Charge | 0 |
| Average Mass | 367.357 |
| Monoisotopic Mass | 367.10559 |
| SMILES | [H][C@@]1([C@]2([H])c3cc4c(cc3CCN2C)OCO4)OC(=O)c2c1ccc1c2OCO1 |
| InChI | InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1 |
| InChIKey | IYGYMKDQCDOMRE-ZWKOTPCHSA-N |
| Wikipedia |
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| Roles Classification |
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| Biological Roles: | neurotoxin A poison that interferes with the functions of the nervous system. GABAA receptor antagonist A GABA receptor antgonist specific for GABAA receptors, ligand-gated ion channels (also known as ionotropic receptors). metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. |
| Applications: | GABAA receptor antagonist A GABA receptor antgonist specific for GABAA receptors, ligand-gated ion channels (also known as ionotropic receptors). agrochemical An agrochemical is a substance that is used in agriculture or horticulture. central nervous system stimulant Any drug that enhances the activity of the central nervous system. |
| ChEBI Ontology |
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| Outgoing Relation(s) |
| bicuculline (CHEBI:3092) has role agrochemical (CHEBI:33286) |
| bicuculline (CHEBI:3092) has role central nervous system stimulant (CHEBI:35337) |
| bicuculline (CHEBI:3092) has role GABA-gated chloride channel antagonist (CHEBI:38999) |
| bicuculline (CHEBI:3092) has role GABAA receptor antagonist (CHEBI:145515) |
| bicuculline (CHEBI:3092) has role neurotoxin (CHEBI:50910) |
| bicuculline (CHEBI:3092) is a benzylisoquinoline alkaloid (CHEBI:22750) |
| bicuculline (CHEBI:3092) is a isoquinoline alkaloid (CHEBI:24921) |
| bicuculline (CHEBI:3092) is a isoquinolines (CHEBI:24922) |
| IUPAC Name |
|---|
| (6R)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e][1,3]benzodioxol-8(6H)-one |
| Synonyms | Source |
|---|---|
| Bicuculline | KEGG COMPOUND |
| Bicculine | ChemIDplus |
| Bicucullin | ChemIDplus |
| d-Bicuculline | ChemIDplus |
| Manual Xrefs | Databases |
|---|---|
| C09364 | KEGG COMPOUND |
| C00001820 | KNApSAcK |
| Bicuculline | Wikipedia |
| Registry Numbers | Sources |
|---|---|
| Beilstein:98786 | Beilstein |
| CAS:485-49-4 | KEGG COMPOUND |
| CAS:485-49-4 | ChemIDplus |
| Citations |
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