Bicuculline

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

Identification

Name
Bicuculline
Accession Number
DB11562
Type
Small Molecule
Groups
Experimental
Description

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.

Structure
Thumb
Synonyms
  • Bicculine
  • Bicucullin
  • d-Bicuculline
Categories
UNII
Y37615DVKC
CAS number
485-49-4
Weight
Average: 367.3521
Monoisotopic: 367.105587281
Chemical Formula
C20H17NO6
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[7.3.0.0²,⁶]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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [PubMed:10398861]
External Links
KEGG Compound
C09364
PubChem Compound
10237
PubChem Substance
347827985
ChemSpider
9820
BindingDB
50000693
ChEBI
3092
ChEMBL
CHEMBL417990
Wikipedia
Bicuculline

Clinical Trials

Clinical Trials
Not Available

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)14.72ChemAxon
pKa (Strongest Basic)7.43ChemAxon
Physiological Charge1ChemAxon
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

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
Phthalide isoquinoline / Benzofuranone / Phthalide / Isobenzofuranone / Tetrahydroisoquinoline / Benzodioxole / Isocoumaran / Aralkylamine / Benzenoid / Amino acid or derivatives
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
isoquinoline alkaloid, isoquinolines (CHEBI:3092) / Isoquinoline alkaloids (C09364)

Drug created on March 29, 2016 10:20 / Updated on November 02, 2018 07:12