Compound: bicuculline
SMILES: O=C1O[C@@H]([C@H]2N(CCc3c2cc4OCOc4c3)C)c5c1c6OCOc6cc5
InChIKey: IYGYMKDQCDOMRE-ZWKOTPCHSA-N
Synonyms: bicuculline, 485-49-4, d-Bicuculline, Bicculine, Bicucullin, Y37615DVKC, (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one, DTXSID3042687, NSC-32192, CHEBI:3092, (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, Furo(3,4-e)-1,3-benzodioxol-8(6H)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (R-(R*,S*))-, (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, (6R)-6-((5S)-6-methyl-7,8-dihydro-5H-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-6H-furo(3,4-g)(1,3)benzodioxol-8-one, (6R)-6-((5S)-6-methyl-7,8-dihydro-5H-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-6H-furo(4,3-g)(1,3)benzodioxol-8-one, (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[4,3-g][1,3]benzodioxol-8-one, RefChem:119660, 6-(5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)furo(3,4-e)1,3-benzodioxol-8(6H)one, DTXCID1022687, (10R)-10-((5S)-6-methyl-2H,5H,6H,7H,8H-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-3,5,11-trioxatricyclo(7.3.0.02,6)dodeca-1(9),2(6),7-trien-12-one, 207-619-7, (+)-Bicuculline, Bicuculline (+), NSC32192, MFCD00005006, CHEMBL417990, (R)-6-((S)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-[1,3]dioxolo[4,5-e]isobenzofuran-8(6H)-one, (6R)-6-[(5S)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one, NSC 32192, (6R)-6-((5S)-6-methyl(5,6,7,8-tetrahydro-2H-1,3-dioxolano[4,5-g]isoquinolin-5- yl))-6-hydro-2H-1,3-dioxoleno[4,5-e]isobenzofuran-8-one, Furo[3,4-e]-1,3-benzodioxol-8(6H)-one, 6-[(5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (6R)-, SR-01000075252, EINECS 207-619-7, BRN 0098786, UNII-Y37615DVKC, D-Bic uculline, bicuculline-(+), IYGYMKDQCDOMRE-ZWKOTPCHSA-N, Bicuculline,(+), Prestwick_96, Furo(3,4-e)-1,3-benzodioxol-8(6H)-one, 6-((5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (6R)-, (+)-Bicuculline?, Bicuculline (Standard), BICUCULLINE [MI], Prestwick0_000589, Prestwick1_000589, Prestwick2_000589, Prestwick3_000589, Biomol-NT_000252, (+)-Bicuculline, 98%, SCHEMBL8222, Lopac0_000234, BSPBio_000438, (6R)-6-[(5S)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]lisoquinolin-5-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one, 4-27-00-06900 (Beilstein Handbook Reference), MLS002153892, DivK1c_000609, SPBio_002657, BPBio1_000482, BPBio1_000794, GTPL2312, orb1304933, orb3139949, SCHEMBL29390611, SCHEMBL29652597, HMS501O11, HY-N0219R, KBio1_000609, NINDS_000609, GLXC-06284, HMS1569F20, HMS2096F20, HMS2235H18, HMS3266A07, HMS3414D19, HMS3652N20, HMS3678D19, HMS3886N09, HY-N0219, BDBM50000693, HB0896, PDSP2_000138, s7071, (+)-Bicuculline - Bio-X trade mark, AKOS024282673, CCG-204329, CS-5493, DB11562, EBC-615949, FB18590, IDI1_000609, NCGC00017385-06, (+)-Bicuculline, >=97.0% (TLC), AC-31293, AS-17471, BB164251, SMR001233241, ST057559, ST057706, NS00031807, SW196408-2, B 9130, B-2400, C09364, Q3639734, SR-01000075252-1, SR-01000075252-4, SR-01000075252-5, WLN: T C566 DO FO KN EH&&TJ K1 J- ET B565 CVO JO LO EH KHJ, (10R)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.0,2,6]dodeca-1,6,8-trien-12-one, (6R)-6-((5S)-6-METHYL-5,6,7,8-TETRAHYDRO(1,3)DIOXOLO(4,5-G)ISOQUINOLIN-5-YL)FURO(3,4-E)(1,3BENZODIOXOL-8(6H)-ONE, (6R)-6-[(5S)-6-Methyl-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2H-furo[3,4-e][1,3]benzodioxol-8(6H)-one, (bicuculline) 6-Methyl-5-(8-oxo-6,8-dihydro-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium, (R)-6-((S)-6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-8-one, (R)-6-((S)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuro[5,4-d][1,3]dioxol-8(6H)-one, 6-((5S)-6-methyl-5,6,7,8-tetrahydro-2H-1,3-dioxoleno[4,5-g]isoquinolin-5-yl)-6 -hydro-2H-1,3-dioxoleno[4,5-e]isobenzofuran-8-one, 6-(6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-8-one, 6-(6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-8-one (Bicuculline), 6-(6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-8-one(bicuculline), Furo[3,3-benzodioxol-8(6H)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [R-(R*,S*)]-, H0Z
Theoretical properties:
molecular_formula: C20H17NO6
molecular_weight: 367.4 g/mol
exact_mass: 367.10558726 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 1
heavy_atom_count: 27
topological_polar_surface_area: 66.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Bicuculline is 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. It has a role as a GABAA receptor antagonist, an agrochemical, a central nervous system stimulant, a GABA-gated chloride channel antagonist and a neurotoxin. It is a benzylisoquinoline alkaloid, an isoquinoline alkaloid and a member of isoquinolines.", "chebi": "A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-<em>g</em>]isoquinoline which is substituted at the 5-<em>pro</em>-<i>S</i> position by a (6<i>R</i>)-8-oxo-6,8-dihydrofuro[3,4-<em>e</em>][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of <a href=\"https://en.wikipedia.org/wiki/GABAA_receptor\" target=\"_blank\">GABA<small><sub>A</sub></small> receptors</a>. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from <em>Dicentra cucullaria</em>, <em>Adlumia fungosa</em>, <em>Fumariaceae</em>, and several <em>Corydalis</em> species.", "chembl": "BICUCULLINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Bicuculline is a phthalide-isoquinoline compound that 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, and several Corydalis species (all in subfamily Fumarioideae, previously known as family Fumariaceae). Since it blocks the inhibitory action of GABA receptors, the action of bicuculline mimics epilepsy; it also causes convulsions. This property is utilized in laboratories around the world in the in vitro study of epilepsy, generally in hippocampal or cortical neurons in prepared brain slices from rodents.  This compound is also routinely used to isolate glutamatergic (excitatory amino acid) receptor function.\nThe action of bicuculline is primarily on the ionotropic GABAA receptors, which are ligand-gated ion channels concerned chiefly with the passing of chloride ions across the cell membrane, thus promoting an inhibitory influence on the target neuron. These receptors are the major targets for benzodiazepines, z-drugs, and related anxiolytic drugs.\nThe half-maximal inhibitory concentration (IC50) of bicuculline on GABAA receptors is 2 \u03bcM +/-0.1 at 40 \u03bcM of GABA (GABA half maximal effective concentration, (EC50)).\nIn addition to being a potent GABAA receptor antagonist, bicuculline can be used to block Ca2+-activated potassium channels.\nSensitivity to bicuculline is defined by IUPHAR as a major criterion in the definition of GABAA receptors."}