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Bicuculline

AlkaPlorer ID: AK000849

Synonym: None

IUPAC Name: (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

Structure

SMILES: CN1CCC2=CC3=C(C=C2[C@H]1[C@@H]1OC(=O)C2=C4OCOC4=CC=C21)OCO3

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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

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InChIKey: IYGYMKDQCDOMRE-ZWKOTPCHSA-N

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Properties Information

Molecule Weight: 367.3570000000001

TPSA？: 66.46000000000001

MolLogP？: 2.5847000000000007

Number of H-Donors: 0

Number of H-Acceptors: 7

RingCount: 6

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter baumannii Acinetobacter baumannii Inhibition -4.97 % 10.6019/CHEMBL4296183
Candida albicans Candida albicans Inhibition -1.4 % 10.6019/CHEMBL4296183
Cryptococcus neoformans Cryptococcus neoformans Inhibition -11.52 % 10.6019/CHEMBL4296183
Electrophorus electricus Acetylcholinesterase Inhibition 20.68 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 0.63 % 10.1016/j.bmc.2012.09.040
Escherichia coli Escherichia coli Inhibition 3.43 % 10.6019/CHEMBL4296183
Homo sapiens Chromobox protein homolog 1 Potency 79432.8 nM None
Homo sapiens GABA-A receptor; anion channel IC50 6200.0 nM 10.1021/jm00100a015
Homo sapiens GABA-A receptor; anion channel IC50 15000.0 nM 10.1021/jm00089a005
Homo sapiens GABA-A receptor; anion channel IC50 44000.0 nM 10.1021/jm00100a015
Homo sapiens GABA receptor alpha-1 subunit Activity nan None 10.1074/jbc.m707233200
Homo sapiens Geminin Potency 2310.9 nM None
Homo sapiens Histone deacetylase 6 Inhibition -5.14 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -2.41 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 25118.9 nM None
Homo sapiens Importin subunit beta-1/Snurportin-1 Potency 70794.6 nM None
Homo sapiens Sodium channel alpha subunits; brain (Types I, II, III) Inhibition 1.8 % 10.1021/jm00381a019
Klebsiella pneumoniae Klebsiella pneumoniae Inhibition 11.38 % 10.6019/CHEMBL4296183
Mus musculus Mus musculus ED50 14.6 mg.kg-1 10.1021/jm901688m
Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition 17.91 % 10.6019/CHEMBL4296183
Rattus norvegicus GABA-A receptor; alpha-1/beta-2/gamma-2 GABA current -100.0 % 10.1016/s0960-894x(00)00514-x
Rattus norvegicus GABA-A receptor; anion channel Displacement -1.0 % 10.1016/s0960-894x(00)00514-x
Rattus norvegicus GABA-A receptor; anion channel Displacement 7.0 % 10.1016/s0960-894x(00)00514-x
Rattus norvegicus GABA-A receptor; anion channel Displacement 45.0 % 10.1016/s0960-894x(00)00514-x
Rattus norvegicus GABA-A receptor; anion channel Inhibition nan % 10.1021/acs.jnatprod.8b01023
Rattus norvegicus GABA-A receptor; anion channel Relative affinity 0.0056 None 10.1021/jm00184a017
Rattus norvegicus GABA receptor gamma-1 subunit IC50 3800.0 nM 10.1021/jm00184a017
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 70794.6 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 21.67 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.05 % 10.6019/CHEMBL4495565
Staphylococcus aureus Staphylococcus aureus Inhibition 11.14 % 10.6019/CHEMBL4296183
None Unchecked Activity nan None 10.1074/jbc.m707233200
None Unchecked Inhibition nan % 10.1038/nchembio873

Metabolism Information