ChemSpider 2D Image | MFCD00238543 | C15H20O3

MFCD00238543

  • Molecular FormulaC15H20O3
  • Average mass248.318 Da
  • Monoisotopic mass248.141251 Da
  • ChemSpider ID137359
  • defined stereocentres - 3 of 3 defined stereocentres


More details:






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

(4aS,8aR,9aS)-9a-Hydroxy-3,8a-dimethyl-5-methylen-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-on [German] [ACD/IUPAC Name]
(4aS,8aR,9aS)-9a-Hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one [ACD/IUPAC Name]
(4aS,8aR,9aS)-9a-Hydroxy-3,8a-diméthyl-5-méthylène-4a,5,6,7,8,8a,9,9a-octahydronaphto[2,3-b]furan-2(4H)-one [French] [ACD/IUPAC Name]
73030-71-4 [RN]
8β-Hydroxyasterolide
Atractylenolide III
Codonolactone
MFCD00238543
Naphtho(2,3-b)furan-2(4H)-one, 4a,5,6,7,8,8a,9,9a-octahydro-9a-hydroxy-3,8a-dimethyl-5-methylene-, (4aS,8aR,9aS)-
Naphtho[2,3-b]furan-2(4H)-one, 4a,5,6,7,8,8a,9,9a-octahydro-9a-hydroxy-3,8a-dimethyl-5-methylene-, (4aS,8aR,9aS)- [ACD/Index Name]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      P261; P262 Biosynth Q-100798
    • Bio Activity:

      Atractylenolide III is a major component of Atractylodes rhizome can induce apoptosis of the lung carcinoma cells. MedChem Express
      Atractylenolide III is a major component of Atractylodes rhizome can induce apoptosis of the lung carcinoma cells.; IC50 value:; Target: Anticancer natural compound; in vitro: ATL-III inhibited cell growth, increased lactate dehydrogenase release and modulated cell cycle on human lung carcinoma A549 cells. MedChem Express HY-N0203
      Atractylenolide III is a major component of Atractylodes rhizome can induce apoptosis of the lung carcinoma cells.;IC50 value:;Target: Anticancer natural compound;In vitro: ATL-III inhibited cell growth, increased lactate dehydrogenase release and modulated cell cycle on human lung carcinoma A549 cells. ALT-III induced the activation of caspase-3 and caspase-9 and cleavage of poly-(ADP)-ribose polymerase. ATL-III induced the release of cytochrome c, upregulation of bax expression, and translocation of apoptosis-inducing factor [1]. Atractylenolide II did not show cytoprotective effects, but oral administration of atractylenolide III dose-dependently prevented ethanol-induced PRGM cell death and cell membrane damage. The EC50 values were 0.27 and 0.34 mm, respectively [2]. Against adult D. pteronyssinus, atractylenolide III (LD50, 73.8 mg/m2) and atractylon (72.1 mg/m2) were eight times more active than Deet and 2.5-fold more toxic than dibutyl phthalate [3].;In vivo: In the in-vi MedChem Express HY-N0203
      Others MedChem Express HY-N0203

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

Density: 1.2±0.1 g/cm3
Boiling Point: 424.6±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.3 mmHg at 25°C
Enthalpy of Vaporization: 78.4±6.0 kJ/mol
Flash Point: 181.1±21.5 °C
Index of Refraction: 1.558
Molar Refractivity: 67.8±0.4 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 2.36
ACD/LogD (pH 5.5): 2.57
ACD/BCF (pH 5.5): 52.77
ACD/KOC (pH 5.5): 594.95
ACD/LogD (pH 7.4): 2.57
ACD/BCF (pH 7.4): 52.74
ACD/KOC (pH 7.4): 594.68
Polar Surface Area: 47 Å2
Polarizability: 26.9±0.5 10-24cm3
Surface Tension: 44.0±5.0 dyne/cm
Molar Volume: 210.0±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) =  3.81

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  374.16  (Adapted Stein & Brown method)
    Melting Pt (deg C):  134.32  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.37E-008  (Modified Grain method)
    Subcooled liquid VP: 1.05E-006 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):  43.9
       log Kow used: 3.81 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  62.275 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Methacrylates
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.46E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.230E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.81  (KowWin est)
  Log Kaw used:  -6.413  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.223
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4356
   Biowin2 (Non-Linear Model)     :   0.5289
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3664  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4115  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5766
   Biowin6 (MITI Non-Linear Model):   0.4378
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5273
 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):  0.00014 Pa (1.05E-006 mm Hg)
  Log Koa (Koawin est  ): 10.223
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0214 
       Octanol/air (Koa) model:  0.0041 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.436 
       Mackay model           :  0.632 
       Octanol/air (Koa) model:  0.247 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 102.7676 E-12 cm3/molecule-sec
      Half-Life =     0.104 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.249 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     8.593750 E-17 cm3/molecule-sec
      Half-Life =     0.133 Days (at 7E11 mol/cm3)
      Half-Life =      3.200 Hrs
   Fraction sorbed to airborne particulates (phi): 0.534 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  173.2
      Log Koc:  2.239 

 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 = 2.231 (BCF = 170.2)
       log Kow used: 3.81 (estimated)

 Volatilization from Water:
    Henry LC:  9.46E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.753E+004  hours   (4064 days)
    Half-Life from Model Lake : 1.064E+006  hours   (4.434E+004 days)

 Removal In Wastewater Treatment:
    Total removal:              22.20  percent
    Total biodegradation:        0.26  percent
    Total sludge adsorption:    21.94  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       0.0403          1.4          1000       
   Water     15.4            900          1000       
   Soil      82.3            1.8e+003     1000       
   Sediment  2.32            8.1e+003     0          
     Persistence Time: 1.26e+003 hr




                    

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