ChemSpider 2D Image | Withanolide | C28H38O6

Withanolide

  • Molecular FormulaC28H38O6
  • Average mass470.598 Da
  • Monoisotopic mass470.266846 Da
  • ChemSpider ID141995
  • defined stereocentres - 11 of 11 defined stereocentres


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

Withanolide
(4β,5β,6β,22R)-4,20-Dihydroxy-5,6:22,26-diepoxyergosta-2,24-dien-1,26-dion [German] [ACD/IUPAC Name]
(4β,5β,6β,22R)-4,20-Dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione [ACD/IUPAC Name]
(4β,5β,6β,22R)-4,20-Dihydroxy-5,6:22,26-diépoxyergosta-2,24-diène-1,26-dione [French] [ACD/IUPAC Name]
Ergosta-2,24-diene-1,26-dione, 5,6:22,26-diepoxy-4,20-dihydroxy-, (4β,5β,6β,22R)- [ACD/Index Name]
withanolide D
(4β,5β,6β,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid δ-lactone
5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid δ-lactone
(4β,5β,6β,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid, δ-lactone
30655-48-2 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C08842 [DBID]
NSC 179841 [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 22 (the 4<stereo>beta</stereo>,5<stereo>beta</stereo>,6<stereo>beta</stereo>,22<s tereo>R</stereo> stereoisomer). Isolated from <ital>Tubocapsicum anomalum</ital> and <ital>Withania somnifera</ital>, it exhibits cytotoxic activity. ChEBI CHEBI:10041
      A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 22 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Tubocapsicum anomalum and Withania somnifera, it exhibits cytotoxic activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:10041

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

Density: 1.3±0.1 g/cm3
Boiling Point: 663.7±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.6 mmHg at 25°C
Enthalpy of Vaporization: 111.7±6.0 kJ/mol
Flash Point: 220.3±25.0 °C
Index of Refraction: 1.600
Molar Refractivity: 125.5±0.4 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 2.89
ACD/LogD (pH 5.5): 3.04
ACD/BCF (pH 5.5): 119.36
ACD/KOC (pH 5.5): 1067.17
ACD/LogD (pH 7.4): 3.04
ACD/BCF (pH 7.4): 119.36
ACD/KOC (pH 7.4): 1067.17
Polar Surface Area: 96 Å2
Polarizability: 49.7±0.5 10-24cm3
Surface Tension: 54.9±5.0 dyne/cm
Molar Volume: 366.8±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) =  2.90

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  593.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  256.26  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.75E-016  (Modified Grain method)
    Subcooled liquid VP: 5.84E-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):  3.692
       log Kow used: 2.90 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  39.198 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Epoxides
       Methacrylates
       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]:  2.935E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.90  (KowWin est)
  Log Kaw used:  -13.562  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.462
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.2198
   Biowin2 (Non-Linear Model)     :   0.0001
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5797  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.8814  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4265
   Biowin6 (MITI Non-Linear Model):   0.0098
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.8342
 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):  7.79E-012 Pa (5.84E-014 mm Hg)
  Log Koa (Koawin est  ): 16.462
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.85E+005 
       Octanol/air (Koa) model:  7.11E+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 = 162.0203 E-12 cm3/molecule-sec
      Half-Life =     0.066 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.792 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    :  162.4
      Log Koc:  2.210 

 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 = 1.532 (BCF = 34.03)
       log Kow used: 2.90 (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:               4.92  percent
    Total biodegradation:        0.12  percent
    Total sludge adsorption:     4.81  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       0.00495         0.413        1000       
   Water     10.4            4.32e+003    1000       
   Soil      89.4            8.64e+003    1000       
   Sediment  0.227           3.89e+004    0          
     Persistence Time: 3.63e+003 hr




                    

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