CHEBI:3092 - bicuculline

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ChEBI Name bicuculline
ChEBI ID CHEBI:3092
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.
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Formula C20H17NO6
Net Charge 0
Average Mass 367.35210
Monoisotopic Mass 367.10559
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
SMILES [H][C@]1(OC(=O)c2c3OCOc3ccc12)[C@@]1([H])N(C)CCc2cc3OCOc3cc12
Roles Classification
Biological Role(s): GABAA receptor antagonist
A GABA receptor antgonist specific for GABAA receptors, ligand-gated ion channels (also known as ionotropic receptors).
GABA-gated chloride channel antagonist

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.
(via alkaloid )
Application(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
Bicculine ChemIDplus
Bicucullin ChemIDplus
Bicuculline KEGG COMPOUND
d-Bicuculline ChemIDplus
Manual Xrefs Databases
Bicuculline Wikipedia
C00001820 KNApSAcK
C09364 KEGG COMPOUND
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Registry Numbers Types Sources
485-49-4 CAS Registry Number KEGG COMPOUND
485-49-4 CAS Registry Number ChemIDplus
98786 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
27579770 PubMed citation Europe PMC
29137474 PubMed citation Europe PMC
29949743 PubMed citation Europe PMC
30858801 PubMed citation Europe PMC
Last Modified
26 November 2019