ChemSpider 2D Image | Limonin | C26H30O8


  • Molecular FormulaC26H30O8
  • Average mass470.512 Da
  • Monoisotopic mass470.194061 Da
  • ChemSpider ID156367
  • defined stereocentres - 9 of 9 defined stereocentres

More details:

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

(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(3-Furyl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromen-3,8,10(6H,9aH)-trion [German] [ACD/IUPAC Name]
(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(3-Furyl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione [ACD/IUPAC Name]
(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(3-Furyl)-6,6,8a,12a-tétraméthyldécahydro-3H-oxiréno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromène-3,8,10(6H,9aH)-trione [French] [ACD/IUPAC Name]
1180-71-8 [RN]
1H,3H-Oxireno[c]pyrano[4'',3'':2',3']furo[3',4':5,6]naphtho[1,2-d]pyran-3,8,10(6H,9aH)-trione, 12-(3-furanyl)decahydro-6,6,8a,12a-tetramethyl-, (4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)- [ACD/Index Name]
Limonin [Wiki]

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

AIDS002683 [DBID]
AIDS-002683 [DBID]
AIDS093234 [DBID]
AIDS-093234 [DBID]
C03514 [DBID]
CHEBI:16226 [DBID]
D00173 [DBID]
KBio3_001983 [DBID]
KBioGR_001659 [DBID]
NSC36508 [DBID]

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

Density: 1.4±0.1 g/cm3
Boiling Point: 668.4±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 98.2±3.0 kJ/mol
Flash Point: 358.0±31.5 °C
Index of Refraction: 1.602
Molar Refractivity: 116.1±0.4 cm3
#H bond acceptors: 8
#H bond donors: 0
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 1.66
ACD/LogD (pH 5.5): 1.60
ACD/BCF (pH 5.5): 9.75
ACD/KOC (pH 5.5): 177.68
ACD/LogD (pH 7.4): 1.60
ACD/BCF (pH 7.4): 9.75
ACD/KOC (pH 7.4): 177.68
Polar Surface Area: 105 Å2
Polarizability: 46.0±0.5 10-24cm3
Surface Tension: 57.5±5.0 dyne/cm
Molar Volume: 338.3±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) =  0.72

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  593.68  (Adapted Stein & Brown method)
    Melting Pt (deg C):  256.36  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.74E-014  (Modified Grain method)
    MP  (exp database):  298 deg C
    Subcooled liquid VP: 1.08E-010 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):  270.2
       log Kow used: 0.72 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  395.18 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.55E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.232E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.72  (KowWin est)
  Log Kaw used:  -13.982  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.702
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.7356
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.3394  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.8179  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6235
   Biowin6 (MITI Non-Linear Model):   0.1010
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.4115
 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):  1.44E-008 Pa (1.08E-010 mm Hg)
  Log Koa (Koawin est  ): 14.702
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  208 
       Octanol/air (Koa) model:  124 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 151.4420 E-12 cm3/molecule-sec
      Half-Life =     0.071 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.848 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  559.8
      Log Koc:  2.748 

 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: 0.72 (estimated)

 Volatilization from Water:
    Henry LC:  2.55E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  4.98E+012  hours   (2.075E+011 days)
    Half-Life from Model Lake : 5.433E+013  hours   (2.264E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               1.87  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.78  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       0.000103        1.7          1000       
   Water     50.1            4.32e+003    1000       
   Soil      49.8            8.64e+003    1000       
   Sediment  0.104           3.89e+004    0          
     Persistence Time: 1.61e+003 hr


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