Bicuculline

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Bicuculline
DrugBank Accession Number
DB11562
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 367.3521
Monoisotopic: 367.105587281
Chemical Formula
C20H17NO6
Synonyms
  • Bicculine
  • Bicucullin
  • d-Bicuculline

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Phthalide isoquinolines
Sub Class
Not Available
Direct Parent
Phthalide isoquinolines
Alternative Parents
Tetrahydroisoquinolines / Phthalides / Benzofuranones / Benzodioxoles / Aralkylamines / Benzenoids / Trialkylamines / Amino acids and derivatives / Lactones / Carboxylic acid esters
show 7 more
Substituents
Acetal / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzodioxole / Benzofuranone / Carboxylic acid derivative
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
isoquinoline alkaloid, isoquinolines (CHEBI:3092) / Isoquinoline alkaloids (C09364)
Affected organisms
Not Available

Chemical Identifiers

UNII
Y37615DVKC
CAS number
485-49-4
InChI Key
IYGYMKDQCDOMRE-ZWKOTPCHSA-N
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
IUPAC Name
(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(9),2(6),7-trien-12-one
SMILES
[H][C@]1(OC(=O)C2=C1C=CC1=C2OCO1)[C@@]1([H])N(C)CCC2=CC3=C(OCO3)C=C12

References

General References
  1. Khawaled R, Bruening-Wright A, Adelman JP, Maylie J: Bicuculline block of small-conductance calcium-activated potassium channels. Pflugers Arch. 1999 Aug;438(3):314-21. [Article]
KEGG Compound
C09364
PubChem Compound
10237
PubChem Substance
347827985
ChemSpider
9820
BindingDB
50000693
ChEBI
3092
ChEMBL
CHEMBL417990
ZINC
ZINC000019899011
PDBe Ligand
H0Z
Wikipedia
Bicuculline
PDB Entries
6huk

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.361 mg/mLALOGPS
logP1.76ALOGPS
logP2.68Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)13.1Chemaxon
pKa (Strongest Basic)6.67Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area66.46 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity93.45 m3·mol-1Chemaxon
Polarizability37.3 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-056s-2592000000-e3973ba2799d460c3b59
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0009000000-7549cdeeb71ef4470dc1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-066r-0009000000-d8e744c493912dace636
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0039000000-01b4f70e0d954ed7658e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004j-0091000000-4bda65b490b53129adf9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0aor-0109000000-40c14a57cb6620310332
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0309000000-7ca1258f5e6afe7f84cd
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-01p9-0906000000-4d63889ee99dca8cab11
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0039000000-b9f59e9657a74348c6a2
MS/MS Spectrum - , positiveLC-MS/MSsplash10-056s-2592000000-e3973ba2799d460c3b59
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0109000000-5348b1d1a6b45c052c0b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-b3d4b47adb086d787a7b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0109000000-37b9fbd7915692abf710
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-d90d40fb81c101aa0270
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0119000000-7036ade2e23eb66262c5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uki-0219000000-f6bf191e6bb590decadb
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-191.9205942
predicted
DarkChem Lite v0.1.0
[M-H]-196.3737942
predicted
DarkChem Lite v0.1.0
[M-H]-175.19753
predicted
DeepCCS 1.0 (2019)
[M+H]+192.6015942
predicted
DarkChem Lite v0.1.0
[M+H]+196.5375942
predicted
DarkChem Lite v0.1.0
[M+H]+177.5931
predicted
DeepCCS 1.0 (2019)
[M+Na]+191.5145942
predicted
DarkChem Lite v0.1.0
[M+Na]+196.2011942
predicted
DarkChem Lite v0.1.0
[M+Na]+183.50562
predicted
DeepCCS 1.0 (2019)

Drug created at March 29, 2016 16:20 / Updated at June 12, 2020 16:53