ChemSpider 2D Image | azadirone | C28H36O4

azadirone

  • Molecular FormulaC28H36O4
  • Average mass436.583 Da
  • Monoisotopic mass436.261353 Da
  • ChemSpider ID9081498

  • defined stereocentres - 7 of 7 defined stereocentres

More details:

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

(5α,7α,13α,17α)-17-(3-Furyl)-4,4,8-trimethyl-3-oxoandrosta-1,14-dien-7-yl acetate [ACD/IUPAC Name]
(5α,7α,13α,17α)-17-(3-Furyl)-4,4,8-trimethyl-3-oxoandrosta-1,14-dien-7-yl-acetat [German] [ACD/IUPAC Name]
25279-67-8 [RN]
Acétate de (5α,7α,13α,17α)-17-(3-furyl)-4,4,8-triméthyl-3-oxoandrosta-1,14-dién-7-yle [French] [ACD/IUPAC Name]
Androsta-1,14-dien-3-one, 7-(acetyloxy)-17-(3-furanyl)-4,4,8-trimethyl-, (5α,7α,13α,17α)- [ACD/Index Name]
azadirone
(5α,7α,13α,17α)-17-(furan-3-yl)-4,4,8-trimethyl-3-oxoandrosta-1,14-dien-7-yl acetate
30002-86-9 [RN]
  • Miscellaneous

    • Chemical Class:

      A tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by an oxo group at position 3, an acetoxy group at position 7 and a furan-3-yl group at position 17. Isolated from <it al>Azadirachta indica</ital>, it exhibits antiplasmodial and antineoplastic activities. ChEBI CHEBI:76293
      A tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by an oxo group at position 3, an acetoxy group at position 7 and a furan-3-yl group at position 17. Isolated from Aza dirachta indica, it exhibits antiplasmodial and antineoplastic activities. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:76293, CHEBI:76293

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

Density: 1.2±0.1 g/cm3
Boiling Point: 506.5±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 77.6±3.0 kJ/mol
Flash Point: 260.1±30.1 °C
Index of Refraction: 1.567
Molar Refractivity: 123.7±0.4 cm3
#H bond acceptors: 4
#H bond donors: 0
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 1
ACD/LogP: 6.22
ACD/LogD (pH 5.5): 5.99
ACD/BCF (pH 5.5): 20975.69
ACD/KOC (pH 5.5): 43158.94
ACD/LogD (pH 7.4): 5.99
ACD/BCF (pH 7.4): 20975.69
ACD/KOC (pH 7.4): 43158.94
Polar Surface Area: 57 Å2
Polarizability: 49.0±0.5 10-24cm3
Surface Tension: 45.1±5.0 dyne/cm
Molar Volume: 378.8±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) =  6.39

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  481.06  (Adapted Stein & Brown method)
    Melting Pt (deg C):  203.75  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.06E-009  (Modified Grain method)
    Subcooled liquid VP: 8.24E-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):  0.006341
       log Kow used: 6.39 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.006742 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Vinyl/Allyl Ketones

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.81E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.603E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.39  (KowWin est)
  Log Kaw used:  -5.808  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.198
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.0397
   Biowin2 (Non-Linear Model)     :   0.0028
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.4287  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.7423  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2974
   Biowin6 (MITI Non-Linear Model):   0.0215
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.1482
 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):  1.1E-005 Pa (8.24E-008 mm Hg)
  Log Koa (Koawin est  ): 12.198
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.273 
       Octanol/air (Koa) model:  0.387 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.908 
       Mackay model           :  0.956 
       Octanol/air (Koa) model:  0.969 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 261.9552 E-12 cm3/molecule-sec
      Half-Life =     0.041 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    29.399 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.312500 E-17 cm3/molecule-sec
      Half-Life =     0.873 Days (at 7E11 mol/cm3)
      Half-Life =     20.955 Hrs
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.932 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.041E+006
      Log Koc:  6.018 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  3.014E-002  L/mol-sec
  Kb Half-Life at pH 8:     266.184  days   
  Kb Half-Life at pH 7:       7.288  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 4.219 (BCF = 1.655e+004)
       log Kow used: 6.39 (estimated)

 Volatilization from Water:
    Henry LC:  3.81E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.211E+004  hours   (1338 days)
    Half-Life from Model Lake : 3.505E+005  hours   (1.46E+004 days)

 Removal In Wastewater Treatment:
    Total removal:              93.26  percent
    Total biodegradation:        0.77  percent
    Total sludge adsorption:    92.49  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       0.00431         0.936        1000       
   Water     1.12            4.32e+003    1000       
   Soil      43.5            8.64e+003    1000       
   Sediment  55.3            3.89e+004    0          
     Persistence Time: 9.89e+003 hr

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