CHEBI:3092 - bicuculline

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ChEBI Name bicuculline
ChEBI ID CHEBI:3092
Definition Bicuculline is 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H17NO6
Net Charge 0
Average Mass 367.35210
Monoisotopic Mass 367.106
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): GABA-gated chloride channel antagonist

GABA antagonist
A compound that inhibits the action of gamma-aminobutyric acid.
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): 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.
GABA antagonist
A compound that inhibits the action of gamma-aminobutyric acid.
View more via ChEBI Ontology
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 antagonist (CHEBI:65259)
bicuculline (CHEBI:3092) has role GABA-gated chloride channel antagonist (CHEBI:38999)
bicuculline (CHEBI:3092) has role neurotoxin (CHEBI:50910)
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
Database Links Databases
C00001820 KNApSAcK
C09364 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
485-49-4 CAS Registry Number KEGG COMPOUND
485-49-4 CAS Registry Number ChemIDplus
98786 Beilstein Registry Number Beilstein
Last Modified
28 July 2014