ChemSpider 2D Image | Picrotoxinin | C15H16O6

Picrotoxinin

  • Molecular FormulaC15H16O6
  • Average mass292.284 Da
  • Monoisotopic mass292.094696 Da
  • ChemSpider ID16498838

  • defined stereocentres - 8 of 8 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(-)-picrotoxinin
(1aR,2aR,3S,6R,6aS,8aS,8bR,9R)-2a-hydroxy-8b-methyl-9-(prop-1-en-2-yl)hexahydro-3,6-methano-1,5,7-trioxacyclopenta[ij]cyclopropa[a]azulene-4,8(3H)-dione
(1R,3R,5S,8S,9R,12S,13R,14R)-1-Hydroxy-13-méthyl-14-(1-propèn-2-yl)-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tétradécane-6,11-dione
(1R,3R,5S,8S,9R,12S,13R,14R)-1-Hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione
(1R,3R,5S,8S,9R,12S,13R,14R)-1-Hydroxy-14-isopropenyl-13-methyl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecan-6,11-dion [German] [ACD/IUPAC Name]
(1R,3R,5S,8S,9R,12S,13R,14R)-1-Hydroxy-14-isopropenyl-13-methyl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione [ACD/IUPAC Name]
(1R,3R,5S,8S,9R,12S,13R,14R)-1-Hydroxy-14-isopropényl-13-méthyl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tétradécane-6,11-dione [French] [ACD/IUPAC Name]
[1aR-(1aa,2ab,3b,6b,6ab,8aS*,8bb,9R*)]-Hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-3,6-methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione
17617-45-7 [RN]
3,6-Methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-, (1aR,2aR,3S,6R,6aS,8aS,8bR,9R)- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

9K011NUF0R [DBID]
C09529 [DBID]
DivK1c_000595 [DBID]
KBio1_000595 [DBID]
KBio2_001772 [DBID]
KBio2_004340 [DBID]
KBio2_006908 [DBID]
KBio3_002394 [DBID]
KBioGR_001402 [DBID]
KBioSS_001772 [DBID]
More...
  • Miscellaneous

    • Chemical Class:

      A picrotoxane sesquiterpenoid that is 3a,4,5,6,7,7a-hexahydro-1<element>H</element>-indene-3,7-dicarboxylic acid which is substituted at positions 3a, 6, and 7a by methyl, isopropenyl, and hydroxy gro ups, respectively; in which the double bond at position 2-3 has been epoxidised; and in which the carboxy groups at positions 3 and 7 have undergone <locant>gamma</locant>-lactone formation by <elemen t>O</element>-alkylation to positions 4 and 5, respectively. A component of picrotoxin. ChEBI CHEBI:8206
      A picrotoxane sesquiterpenoid that is 3a,4,5,6,7,7a-hexahydro-1H-indene-3,7-dicarboxylic acid which is substituted at positions 3a, 6, and 7a by methyl, isopropenyl, and hydroxy groups, respectively; in which the double bond at position 2-3 has been epoxidised; and in which the carboxy groups at positions 3 and 7 have undergone gamma-lactone formation by O-alkylation to positions 4 and 5, respecti vely. A component of picrotoxin. ChEBI CHEBI:8206

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.5±0.1 g/cm3
Boiling Point: 551.6±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.4 mmHg at 25°C
Enthalpy of Vaporization: 95.6±6.0 kJ/mol
Flash Point: 214.0±23.6 °C
Index of Refraction: 1.625
Molar Refractivity: 67.7±0.4 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: -0.13
ACD/LogD (pH 5.5): -0.02
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 23.36
ACD/LogD (pH 7.4): -0.02
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 23.36
Polar Surface Area: 85 Å2
Polarizability: 26.9±0.5 10-24cm3
Surface Tension: 61.3±5.0 dyne/cm
Molar Volume: 191.5±5.0 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) =  -1.72

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  439.55  (Adapted Stein & Brown method)
    Melting Pt (deg C):  176.05  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.38E-010  (Modified Grain method)
    Subcooled liquid VP: 1.25E-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):  1e+006
       log Kow used: -1.72 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3567.3 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Epoxides
       Esters

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.89E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.304E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.72  (KowWin est)
  Log Kaw used:  -11.393  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.673
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.0571
   Biowin2 (Non-Linear Model)     :   0.1685
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1864  (months      )
   Biowin4 (Primary Survey Model) :   3.4124  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8265
   Biowin6 (MITI Non-Linear Model):   0.4319
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3091
 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):  1.67E-006 Pa (1.25E-008 mm Hg)
  Log Koa (Koawin est  ): 9.673
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.8 
       Octanol/air (Koa) model:  0.00116 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.985 
       Mackay model           :  0.993 
       Octanol/air (Koa) model:  0.0847 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  64.9777 E-12 cm3/molecule-sec
      Half-Life =     0.165 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.975 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.200000 E-17 cm3/molecule-sec
      Half-Life =     0.955 Days (at 7E11 mol/cm3)
      Half-Life =     22.920 Hrs
   Fraction sorbed to airborne particulates (phi): 0.989 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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: -1.72 (estimated)

 Volatilization from Water:
    Henry LC:  9.89E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.014E+010  hours   (4.224E+008 days)
    Half-Life from Model Lake : 1.106E+011  hours   (4.608E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       9.96e-005       3.37         1000       
   Water     49.5            1.44e+003    1000       
   Soil      50.4            2.88e+003    1000       
   Sediment  0.0962          1.3e+004     0          
     Persistence Time: 1.17e+003 hr

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