ChemSpider 2D Image | L6DO3QW4K5 | C28H38O6

L6DO3QW4K5

  • Molecular FormulaC28H38O6
  • Average mass470.598 Da
  • Monoisotopic mass470.266846 Da
  • ChemSpider ID233064
  • defined stereocentres - 11 of 11 defined stereocentres


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(4b,5b,6b,22R)-5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid d-lactone
(4β,5β,6β,22R)-4,27-Dihydroxy-5,6:22,26-diepoxyergosta-2,24-dien-1,26-dion [German] [ACD/IUPAC Name]
(4β,5β,6β,22R)-4,27-Dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione [ACD/IUPAC Name]
(4β,5β,6β,22R)-4,27-Dihydroxy-5,6:22,26-diépoxyergosta-2,24-diène-1,26-dione [French] [ACD/IUPAC Name]
4b,27-Dihydroxy-1-oxo-5b,6b-epoxywitha-2,24-dienolide
5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oic Acid d-Lactone
5119-48-2 [RN]
Ergosta-2,24-diene-1,26-dione, 5,6:22,26-diepoxy-4,27-dihydroxy-, (4β,5β,6β,22R)- [ACD/Index Name]
L6DO3QW4K5
Withaferin A
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C08841 [DBID]
NCI60_000031 [DBID]
NSC101088 [DBID]
NSC273757 [DBID]
  • Miscellaneous
    • Chemical Class:

      A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4<stereo>beta</stereo>,5<stereo>beta</stereo>,6<stereo>beta</stereo>,22<s tereo>R</stereo> stereoisomer). Isolated from <ital>Physalis longifolia</ital>, it exhibits cytotoxic activity. ChEBI CHEBI:69120

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

Density: 1.3±0.1 g/cm3
Boiling Point: 680.7±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.8 mmHg at 25°C
Enthalpy of Vaporization: 114.3±6.0 kJ/mol
Flash Point: 226.7±25.0 °C
Index of Refraction: 1.599
Molar Refractivity: 125.4±0.4 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 3.80
ACD/LogD (pH 5.5): 3.32
ACD/BCF (pH 5.5): 196.96
ACD/KOC (pH 5.5): 1527.29
ACD/LogD (pH 7.4): 3.32
ACD/BCF (pH 7.4): 196.96
ACD/KOC (pH 7.4): 1527.29
Polar Surface Area: 96 Å2
Polarizability: 49.7±0.5 10-24cm3
Surface Tension: 55.1±5.0 dyne/cm
Molar Volume: 367.0±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) =  2.94

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  607.25  (Adapted Stein & Brown method)
    Melting Pt (deg C):  262.70  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.16E-017  (Modified Grain method)
    Subcooled liquid VP: 2.07E-014 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):  3.429
       log Kow used: 2.94 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  26.69 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.70E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.318E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.94  (KowWin est)
  Log Kaw used:  -13.562  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.502
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1228
   Biowin2 (Non-Linear Model)     :   0.0016
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9518  (months      )
   Biowin4 (Primary Survey Model) :   3.1643  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5184
   Biowin6 (MITI Non-Linear Model):   0.0240
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.4275
 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):  2.76E-012 Pa (2.07E-014 mm Hg)
  Log Koa (Koawin est  ): 16.502
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.09E+006 
       Octanol/air (Koa) model:  7.8E+003 
   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 = 153.0992 E-12 cm3/molecule-sec
      Half-Life =     0.070 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.838 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    49.196873 E-17 cm3/molecule-sec
      Half-Life =     0.023 Days (at 7E11 mol/cm3)
      Half-Life =     33.544 Min
   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    :  208.6
      Log Koc:  2.319 

 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 = 1.561 (BCF = 36.37)
       log Kow used: 2.94 (estimated)

 Volatilization from Water:
    Henry LC:  6.7E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.896E+012  hours   (7.899E+010 days)
    Half-Life from Model Lake : 2.068E+013  hours   (8.617E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               5.21  percent
    Total biodegradation:        0.12  percent
    Total sludge adsorption:     5.09  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       0.0124          0.419        1000       
   Water     16.2            1.44e+003    1000       
   Soil      83.4            2.88e+003    1000       
   Sediment  0.353           1.3e+004     0          
     Persistence Time: 1.54e+003 hr




                    

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