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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: | GABAA receptor antagonist A GABA receptor antgonist specific for GABAA receptors, ligand-gated ion channels (also known as ionotropic receptors). neurotoxin A poison that interferes with the functions of the nervous system. 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 |
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| (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 |
|---|---|
| Bicculine | ChemIDplus |
| Bicucullin | ChemIDplus |
| Bicuculline | KEGG COMPOUND |
| d-Bicuculline | ChemIDplus |
| Manual Xrefs | Databases |
|---|---|
| Bicuculline | Wikipedia |
| C00001820 | KNApSAcK |
| C09364 | KEGG COMPOUND |
| Registry Numbers | Sources |
|---|---|
| Beilstein:98786 | Beilstein |
| CAS:485-49-4 | ChemIDplus |
| CAS:485-49-4 | KEGG COMPOUND |
| Citations |
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