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Search term: 9604856 (Found by CSID)
ChemSpider 2D Image | 5alpha,8alpha-epidioxycholest-6-en-3beta-ol | C27H44O3

5α,8α-epidioxycholest-6-en-3β-ol

  • Molecular FormulaC27H44O3
  • Average mass416.637 Da
  • Monoisotopic mass416.329041 Da
  • ChemSpider ID9604856

  • defined stereocentres - 9 of 9 defined stereocentres

More details:

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

(1S,2R,5R,6R,9R,10R,13S,15S)-6,10-Dimethyl-5-[(2R)-6-methyl-2-heptanyl]-16,17-dioxapentacyclo[13.2.2.01,9.02,6.010,15]nonadec-18-en-13-ol [German] [ACD/IUPAC Name]
(1S,2R,5R,6R,9R,10R,13S,15S)-6,10-Dimethyl-5-[(2R)-6-methyl-2-heptanyl]-16,17-dioxapentacyclo[13.2.2.01,9.02,6.010,15]nonadec-18-en-13-ol [ACD/IUPAC Name]
(1S,2R,5R,6R,9R,10R,13S,15S)-6,10-Diméthyl-5-[(2R)-6-méthyl-2-heptanyl]-16,17-dioxapentacyclo[13.2.2.01,9.02,6.010,15]nonadéc-18-én-13-ol [French] [ACD/IUPAC Name]
14231-33-5 [RN]
3b,5a-Etheno-1H-benz[c]indeno[5,4-e][1,2]dioxin-7-ol, 1-[(1R)-1,5-dimethylhexyl]-2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-9a,11a-dimethyl-, (1R,3aR,3bS,5aS,7S,9aR,9bR,11aR)- [ACD/Index Name]
5α,8α-epidioxycholest-6-en-3β-ol
(3S,5S,8S,9R,10R,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-ol
1e
5??,8??-epidioxycholest-6-en-3??-ol
5α,8α-epidioxy-cholest-6-en-3β-ol
More...
  • Miscellaneous

    • Chemical Class:

      A cholestanoid that is cholest-6-ene substituted by a <stereo>beta</stereo>-hydroxy group at position 3 and a peroxy group between positions 5 and 8 (the 5<stereo>alpha</stereo>,8<stereo>alpha</stereo > stereoisomer). Isolated from the sea urchin <ital>Diadema setosum</ital>, it exhibits cytotoxicity against variuos cancer cell lines. ChEBI CHEBI:65851
      A cholestanoid that is cholest-6-ene substituted by a beta-hydroxy group at position 3 and a peroxy group between positions 5 and 8 (the 5alpha,8alpha stereoisomer). Isolated from the sea urchin Diade ma setosum, it exhibits cytotoxicity against variuos cancer cell lines. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65851, CHEBI:65851

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

Density: 1.1±0.1 g/cm3
Boiling Point: 491.9±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.8 mmHg at 25°C
Enthalpy of Vaporization: 87.4±6.0 kJ/mol
Flash Point: 251.3±28.7 °C
Index of Refraction: 1.545
Molar Refractivity: 121.7±0.4 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: 7.85
ACD/LogD (pH 5.5): 7.24
ACD/BCF (pH 5.5): 186449.70
ACD/KOC (pH 5.5): 206178.92
ACD/LogD (pH 7.4): 7.24
ACD/BCF (pH 7.4): 186449.70
ACD/KOC (pH 7.4): 206178.92
Polar Surface Area: 39 Å2
Polarizability: 48.2±0.5 10-24cm3
Surface Tension: 42.4±5.0 dyne/cm
Molar Volume: 385.0±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) =  9.19

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  451.90  (Adapted Stein & Brown method)
    Melting Pt (deg C):  190.13  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.93E-011  (Modified Grain method)
    Subcooled liquid VP: 5.34E-009 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):  0.0001108
       log Kow used: 9.19 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5.3362e-005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.39E-006  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.913E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  9.19  (KowWin est)
  Log Kaw used:  -4.245  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.435
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.0278
   Biowin2 (Non-Linear Model)     :   0.0002
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5899  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.7623  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1534
   Biowin6 (MITI Non-Linear Model):   0.0108
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.8490
 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):  7.12E-007 Pa (5.34E-009 mm Hg)
  Log Koa (Koawin est  ): 13.435
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.21 
       Octanol/air (Koa) model:  6.68 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.993 
       Mackay model           :  0.997 
       Octanol/air (Koa) model:  0.998 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  94.3143 E-12 cm3/molecule-sec
      Half-Life =     0.113 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.361 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.175000 E-17 cm3/molecule-sec
      Half-Life =     6.549 Days (at 7E11 mol/cm3)
   Fraction sorbed to airborne particulates (phi): 0.995 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4.343E+006
      Log Koc:  6.638 

 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 = 1.810 (BCF = 64.58)
       log Kow used: 9.19 (estimated)

 Volatilization from Water:
    Henry LC:  1.39E-006 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      861.9  hours   (35.91 days)
    Half-Life from Model Lake :       9573  hours   (398.9 days)

 Removal In Wastewater Treatment:
    Total removal:              94.03  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.26  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       0.0101          2.68         1000       
   Water     0.73            4.32e+003    1000       
   Soil      41              8.64e+003    1000       
   Sediment  58.3            3.89e+004    0          
     Persistence Time: 1.1e+004 hr

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