ChemSpider 2D Image | (+)-Bicuculline | C20H17NO6

(+)-Bicuculline

  • Molecular FormulaC20H17NO6
  • Average mass367.352 Da
  • Monoisotopic mass367.105591 Da
  • ChemSpider ID9820
  • defined stereocentres - 2 of 2 defined stereocentres


More details:



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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(+)-Bicuculline
(6R)-6-[(5S)-6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isochinolin-5-yl]furo[3,4-e][1,3]benzodioxol-8(6H)-on [German] [ACD/IUPAC Name]
(6R)-6-[(5S)-6-Méthyl-5,6,7,8-tétrahydro[1,3]dioxolo[4,5-g]isoquinoléin-5-yl]furo[3,4-e][1,3]benzodioxol-8(6H)-one [French] [ACD/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 [ACD/IUPAC Name]
207-619-7 [EINECS]
2-Ethoxybenzoic acid [ACD/IUPAC Name]
485-49-4 [RN]
98786
Bicuculline [Wiki]
BICUCULLINE (+)
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Y37615DVKC [DBID]
14340_FLUKA [DBID]
BRN 0098786 [DBID]
C09364 [DBID]
DivK1c_000609 [DBID]
KBio1_000609 [DBID]
NINDS_000609 [DBID]
NSC 32192 [DBID]
NSC32192 [DBID]
Prestwick_96 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Off-white to yellow powder Chemodex B0239
      Off-white to yellow powder. Chemodex B0239
    • Toxicity:

      Organic Compound; Amine; Ester; Plant Toxin; Natural Compound Toxin, Toxin-Target Database T3D4073
    • Target Organs:

      GABAR antagonist TargetMol T2850
    • Chemical Class:

      Bicuculline is a light-sensitive competitive antagonist of GABA<smallsub>A</smallsub> receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from <ital>Dicent ra cucullaria</ital>, <ital>Adlumia fungosa</ital>, <ital>Fumariaceae</ital>, and several <ital>Corydalis</ital> species. ChEBI CHEBI:3092
      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 Dicent; ra cucullaria, Adlumia fu ngosa, Fumariaceae, and several Corydalis species. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3092
    • Bio Activity:

      (+)-Bicuculline, a convulsant alkaloid, is the antagonist of GABA. MedChem Express HY-N0219
      <p></p> <p>Prototypic, competitive GABA<sub>A</sub> receptor antagonist which displaces <a href=gaba.html title=GABA | GABAA agonist | Hello Bio target=_self>GABA</a> from the agonist binding site to prevent receptor activation.&nbsp;</p> <p>Also acts as a negative allosteric inhibitor of channel opening to inhibit GABA<sub>A</sub> receptor activation by anaesthetic agents.</p> <p><br />Reversibly and competitively blocks GABA<sub>A</sub> receptor mediated currents. Widely used to isolate glutamate receptor mediated EPSCs (excitatory postsynaptic potentials).</p> <p><br />Shows convulsant action and induces epilepsy.</p> <p></p> <p>Water soluble <a href=bicuculline-methiodide.html title=(-)-Bicuculline methiodide | GABAAR antagonist | Hello Bio target=_self>methiodide</a>,&nbsp;<a href=bicuculline-methochloride.html title=(-)-Bicuculline methochloride | GABAAR antagonist | Hello Bio target=_self>methochloride</a>&nbsp;and <a href=bicuculline-methobromide.html title=(-)-Bicuculline methobromide | GABAAR antagonist | Hello Bio target=_self>methobromide</a>&nbsp;salts also available.</p> Hello Bio HB0896
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB0896
      Classical GABAA antagonist. Methoiodide salt (Cat. No. 2503), Methobromide salt (Cat. No. 0109) and Methochloride salt (Cat. No. 0131) also available. Tocris Bioscience 0130, 130
      Classical GABAA antagonist. Methoiodide Salt, Methobromide Salt and Methochloride Salt also available. Tocris Bioscience 130
      GABA Receptor MedChem Express HY-N0219
      GABAA and A-rho Receptors Tocris Bioscience 130
      GABAA receptor TargetMol T2850
      Ion Channels Tocris Bioscience 130
      Ion channels/Ligand-gated ion channel/GABA<sub>A</sub> Hello Bio HB0896
      Ligand-gated Ion Channels Tocris Bioscience 130
      Membrane Transporter/Ion Channel; MedChem Express HY-N0219
      Neuroscience TargetMol T2850
      Potent GABAA antagonist Tocris Bioscience 0130, 130
      Prototypic, competitive GABA<sub>A</sub> receptor antagonist Hello Bio HB0896

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.5±0.1 g/cm3
Boiling Point: 542.3±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 82.0±3.0 kJ/mol
Flash Point: 281.8±30.1 °C
Index of Refraction: 1.665
Molar Refractivity: 92.6±0.3 cm3
#H bond acceptors: 7
#H bond donors: 0
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 2.88
ACD/LogD (pH 5.5): 1.32
ACD/BCF (pH 5.5): 3.00
ACD/KOC (pH 5.5): 34.08
ACD/LogD (pH 7.4): 2.47
ACD/BCF (pH 7.4): 42.64
ACD/KOC (pH 7.4): 484.35
Polar Surface Area: 66 Å2
Polarizability: 36.7±0.5 10-24cm3
Surface Tension: 61.5±3.0 dyne/cm
Molar Volume: 249.4±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -0.86

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  500.42  (Adapted Stein & Brown method)
    Melting Pt (deg C):  212.79  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.7E-010  (Modified Grain method)
    Subcooled liquid VP: 2.68E-008 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  2.652e+005
       log Kow used: -0.86 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5073.7 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylates
       Aliphatic Amines
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.30E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.935E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.86  (KowWin est)
  Log Kaw used:  -12.275  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.415
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.3144
   Biowin2 (Non-Linear Model)     :   0.0004
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1116  (months      )
   Biowin4 (Primary Survey Model) :   3.2366  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1102
   Biowin6 (MITI Non-Linear Model):   0.0114
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.4874
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  3.57E-006 Pa (2.68E-008 mm Hg)
  Log Koa (Koawin est  ): 11.415
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.84 
       Octanol/air (Koa) model:  0.0638 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.968 
       Mackay model           :  0.985 
       Octanol/air (Koa) model:  0.836 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 308.1686 E-12 cm3/molecule-sec
      Half-Life =     0.035 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    24.990 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     9.639999 E-17 cm3/molecule-sec
      Half-Life =     0.119 Days (at 7E11 mol/cm3)
      Half-Life =      2.853 Hrs
   Fraction sorbed to airborne particulates (phi): 0.977 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  16.88
      Log Koc:  1.227 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -0.86 (estimated)

 Volatilization from Water:
    Henry LC:  1.3E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.644E+010  hours   (3.602E+009 days)
    Half-Life from Model Lake :  9.43E+011  hours   (3.929E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       7.16e-006       0.645        1000       
   Water     49.4            1.44e+003    1000       
   Soil      50.5            2.88e+003    1000       
   Sediment  0.0961          1.3e+004     0          
     Persistence Time: 1.17e+003 hr




                    

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