ChemSpider 2D Image | atractylenolide I | C15H18O2

atractylenolide I

  • Molecular FormulaC15H18O2
  • Average mass230.302 Da
  • Monoisotopic mass230.130676 Da
  • ChemSpider ID4478915

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(4aS,8aS)-3,8a-Dimethyl-5-methylen-4a,5,6,7,8,8a-hexahydronaphtho[2,3-b]furan-2(4H)-on [German] [ACD/IUPAC Name]
(4aS,8aS)-3,8a-Dimethyl-5-methylene-4a,5,6,7,8,8a-hexahydronaphtho[2,3-b]furan-2(4H)-one [ACD/IUPAC Name]
(4aS,8aS)-3,8a-Diméthyl-5-méthylène-4a,5,6,7,8,8a-hexahydronaphto[2,3-b]furan-2(4H)-one [French] [ACD/IUPAC Name]
73069-13-3 [RN]
atractylenolide I
Naphtho[2,3-b]furan-2(4H)-one, 4a,5,6,7,8,8a-hexahydro-3,8a-dimethyl-5-methylene-, (4aS,8aS)- [ACD/Index Name]
(4aS,8aS)-3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH-naphtho[2,3-b]furan-2-one
(4aS,8aS)-3,8a-dimethyl-5-methylidene-4a,5,6,7,8,8a-hexahydronaphtho[2,3-b]furan-2(4H)-one
(4aS,8aS)-3,8a-dimethyl-5-methylidene-4a,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-2-one
[73069-13-3] [RN]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Bio Activity:

      Atractylenolide I is a natural compound extracted from largehead atractylodes rhizome; induce apoptosis and bring about cytotoxicity of human promyeloleukemic HL-60 cells; TLR4-antagonizing agent. MedChem Express
      Atractylenolide I is a natural compound extracted from largehead atractylodes rhizome; induce apoptosis and bring about cytotoxicity of human promyeloleukemic HL-60 cells; TLR4-antagonizing agent.; IC50 value:; Target: TLR4 antagonist; in vitro: The ID(50) values of atractylenolide I were 15.15 mg/kg and 3.89 microg/ml for inhibiting the vascular index in vivo and microvessel outgrowth in vitro, respectively. MedChem Express HY-N0201
      Immunology/Inflammation MedChem Express HY-N0201
      Immunology/Inflammation; MedChem Express HY-N0201
      Toll-like Receptor (TLR) MedChem Express HY-N0201

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

Density: 1.1±0.1 g/cm3
Boiling Point: 405.0±44.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 65.6±3.0 kJ/mol
Flash Point: 170.8±25.9 °C
Index of Refraction: 1.555
Molar Refractivity: 65.9±0.4 cm3
#H bond acceptors: 2
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 3.77
ACD/LogD (pH 5.5): 3.60
ACD/BCF (pH 5.5): 320.89
ACD/KOC (pH 5.5): 2166.01
ACD/LogD (pH 7.4): 3.60
ACD/BCF (pH 7.4): 320.89
ACD/KOC (pH 7.4): 2166.01
Polar Surface Area: 26 Å2
Polarizability: 26.1±0.5 10-24cm3
Surface Tension: 38.5±5.0 dyne/cm
Molar Volume: 205.3±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) =  3.32

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  349.89  (Adapted Stein & Brown method)
    Melting Pt (deg C):  112.31  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.83E-005  (Modified Grain method)
    Subcooled liquid VP: 0.000133 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):  44.39
       log Kow used: 3.32 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  6.5108 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.47E-003  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.249E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.32  (KowWin est)
  Log Kaw used:  -1.221  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  4.541
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6282
   Biowin2 (Non-Linear Model)     :   0.8904
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6183  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5910  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5491
   Biowin6 (MITI Non-Linear Model):   0.4166
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1466
 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):  0.0177 Pa (0.000133 mm Hg)
  Log Koa (Koawin est  ): 4.541
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000169 
       Octanol/air (Koa) model:  8.53E-009 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00607 
       Mackay model           :  0.0134 
       Octanol/air (Koa) model:  6.82E-007 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 159.5120 E-12 cm3/molecule-sec
      Half-Life =     0.067 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.805 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    35.422501 E-17 cm3/molecule-sec
      Half-Life =     0.032 Days (at 7E11 mol/cm3)
      Half-Life =     46.587 Min
   Fraction sorbed to airborne particulates (phi): 0.00971 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  3749
      Log Koc:  3.574 

 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 = 1.856 (BCF = 71.71)
       log Kow used: 3.32 (estimated)

 Volatilization from Water:
    Henry LC:  0.00147 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      2.153  hours
    Half-Life from Model Lake :      150.7  hours   (6.281 days)

 Removal In Wastewater Treatment:
    Total removal:              42.34  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     7.69  percent
    Total to Air:               34.54  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.0857          0.524        1000       
   Water     15              900          1000       
   Soil      84.2            1.8e+003     1000       
   Sediment  0.712           8.1e+003     0          
     Persistence Time: 577 hr

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