ChemSpider 2D Image | (3beta,5alpha,22E)-3,5,9-Trihydroxyergosta-7,22-dien-6-one | C28H44O4

(3β,5α,22E)-3,5,9-Trihydroxyergosta-7,22-dien-6-one

  • Molecular FormulaC28H44O4
  • Average mass444.647 Da
  • Monoisotopic mass444.323975 Da
  • ChemSpider ID10398057

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 9 of 9 defined stereocentres

More details:

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

(22E,24R)-3β,5α,9α-trihydroxyergosta-7,22-dien-6-one
(3β,5α,22E)-3,5,9-Trihydroxyergosta-7,22-dien-6-on [German] [ACD/IUPAC Name]
(3β,5α,22E)-3,5,9-Trihydroxyergosta-7,22-dien-6-one [ACD/IUPAC Name]
(3β,5α,22E)-3,5,9-Trihydroxyergosta-7,22-dién-6-one [French] [ACD/IUPAC Name]
Ergosta-7,22-dien-6-one, 3,5,9-trihydroxy-, (3β,5α,22E)- [ACD/Index Name]
(3S,5R,9R,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3,5,9-trihydroxy-10,13-dimethyl-1,2,3,4,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
3,5,9-Trihydroxyergosta-7,22-dien-6-one
3??,5??,9??-trihydroxy-(22E,24R)-ergosta-7,22-dien-6-one
3??,5??,9??-Trihydroxyergosta-7,22-dien-6-one
88191-14-4 [RN]
More...
  • Miscellaneous

    • Chemical Class:

      An ergostanoid that is (22<stereo>E</stereo>)-ergosta-7,22-diene substituted by hydroxy groups at positions 3, 5 and 9 and an oxo group at position 6 (the 3<stereo>beta</stereo>,5<stereo>alpha</stere o> stereoisomer). It has been isolated from <ital>Aspergillus ochraceus</ital>. ChEBI CHEBI:70335
      An ergostanoid that is (22E)-ergosta-7,22-diene substituted by hydroxy groups at positions 3, 5 and 9 and an oxo group at position 6 (the 3beta,5alpha stereoisomer). It has been isolated from Aspergi llus ochraceus. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:70335, CHEBI:70335

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

Density: 1.1±0.1 g/cm3
Boiling Point: 581.3±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.7 mmHg at 25°C
Enthalpy of Vaporization: 99.8±6.0 kJ/mol
Flash Point: 319.4±26.6 °C
Index of Refraction: 1.564
Molar Refractivity: 127.7±0.4 cm3
#H bond acceptors: 4
#H bond donors: 3
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 1
ACD/LogP: 5.51
ACD/LogD (pH 5.5): 4.81
ACD/BCF (pH 5.5): 2665.65
ACD/KOC (pH 5.5): 9857.92
ACD/LogD (pH 7.4): 4.81
ACD/BCF (pH 7.4): 2665.58
ACD/KOC (pH 7.4): 9857.67
Polar Surface Area: 78 Å2
Polarizability: 50.6±0.5 10-24cm3
Surface Tension: 48.3±5.0 dyne/cm
Molar Volume: 392.5±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) =  6.20

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  530.00  (Adapted Stein & Brown method)
    Melting Pt (deg C):  226.61  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.35E-014  (Modified Grain method)
    Subcooled liquid VP: 1.96E-012 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):  0.008105
       log Kow used: 6.20 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.79615 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.27E-007  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.745E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.20  (KowWin est)
  Log Kaw used:  -5.032  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.232
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.0343
   Biowin2 (Non-Linear Model)     :   0.0001
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5055  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.6997  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0169
   Biowin6 (MITI Non-Linear Model):   0.0033
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.6773
 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):  2.61E-010 Pa (1.96E-012 mm Hg)
  Log Koa (Koawin est  ): 11.232
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.15E+004 
       Octanol/air (Koa) model:  0.0419 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.77 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 172.5475 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 180.1475 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.744 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.712 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    14.137500 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    21.137501 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     1.945 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.301 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Reaction With Nitrate Radicals May Be Important!
   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    :  1.607E+004
      Log Koc:  4.206 

 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 = 4.077 (BCF = 1.194e+004)
       log Kow used: 6.20 (estimated)

 Volatilization from Water:
    Henry LC:  2.27E-007 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       5441  hours   (226.7 days)
    Half-Life from Model Lake : 5.953E+004  hours   (2481 days)

 Removal In Wastewater Treatment:
    Total removal:              92.84  percent
    Total biodegradation:        0.77  percent
    Total sludge adsorption:    92.07  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       0.00409         0.843        1000       
   Water     1.31            4.32e+003    1000       
   Soil      45.2            8.64e+003    1000       
   Sediment  53.5            3.89e+004    0          
     Persistence Time: 9.47e+003 hr

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