ChemSpider 2D Image | 20a-Hydroxycholesterol | C27H46O2

20a-Hydroxycholesterol

  • Molecular FormulaC27H46O2
  • Average mass402.653 Da
  • Monoisotopic mass402.349792 Da
  • ChemSpider ID389586
  • defined stereocentres - 8 of 8 defined stereocentres


More details:






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

(3b,20R)-Cholest-5-ene-3,20-diol
(3β,20R)-Cholest-5-en-3,20-diol [German] [ACD/IUPAC Name]
(3β,20R)-Cholest-5-ene-3,20-diol [ACD/IUPAC Name]
(3β,20R)-Cholest-5-ène-3,20-diol [French] [ACD/IUPAC Name]
20a-Hydroxycholesterol
20α-HYDROXYCHOLESTEROL
516-72-3 [RN]
Cholest-5-ene-3,20-diol, (3β,20R)- [ACD/Index Name]
nat-20(R)-Hydroxycholesterol
(1S,2R,5S,10S,11S,14S,15S)-14-[(2R)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-ol
More...

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

C05500 [DBID]
CCRIS 4693 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Bio Activity:

      Allosteric activator of Hedgehog (Hh) signaling; induces Smo accumulation Tocris Bioscience 4474
      Allosteric activator of the Hedgehog signaling pathway Smoothened (Smo) oncoprotein; binds at a site distinct from the canonical cyclopamine binding site. Activates Hedgehog (Hh) signaling (EC50 ~ 3?M for induction of Hh reporter gene transcription in in NIH 3T3 cells). Induces Smo accumulation in primary cilia; also exhibits osteogenic activity and activates the liver X receptor (LXR). Tocris Bioscience 4474
      Allosteric activator of the Hedgehog signaling pathway Smoothened (Smo) oncoprotein; binds at a site distinct from the canonical cyclopamine binding site. Activates Hedgehog (Hh) signaling (EC50 ~ 3?M for induction of Hh reporter gene transcription in in NIH 3T3 cells). Induces Smo accumulation in primary cilia; also exhibits osteogenic activity and activates the liver X receptor (LXR). Tocris Bioscience 4474
      Allosteric activator of the Hedgehog signaling pathway Smoothened (Smo) oncoprotein; binds at a site distinct from the canonical cyclopamine binding site. Activates Hedgehog (Hh) signaling (EC50 ~ 3muM for induction of Hh reporter gene transcription in in NIH 3T3 cells). Induces Smo accumulation in primary cilia; also exhibits osteogenic activity and activates the liver X receptor (LXR). Tocris Bioscience 4474
      Cell Biology Tocris Bioscience 4474
      Hedgehog Signaling Tocris Bioscience 4474
      Signal Transduction Tocris Bioscience 4474

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

Density: 1.0±0.1 g/cm3
Boiling Point: 512.3±23.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.0 mmHg at 25°C
Enthalpy of Vaporization: 90.2±6.0 kJ/mol
Flash Point: 213.1±17.2 °C
Index of Refraction: 1.538
Molar Refractivity: 121.5±0.4 cm3
#H bond acceptors: 2
#H bond donors: 2
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: 7.66
ACD/LogD (pH 5.5): 6.64
ACD/BCF (pH 5.5): 66134.33
ACD/KOC (pH 5.5): 98184.41
ACD/LogD (pH 7.4): 6.64
ACD/BCF (pH 7.4): 66134.33
ACD/KOC (pH 7.4): 98184.41
Polar Surface Area: 40 Å2
Polarizability: 48.2±0.5 10-24cm3
Surface Tension: 41.9±5.0 dyne/cm
Molar Volume: 388.5±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) =  7.64

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  462.45  (Adapted Stein & Brown method)
    Melting Pt (deg C):  191.58  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.64E-011  (Modified Grain method)
    Subcooled liquid VP: 9.17E-010 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):  0.0008765
       log Kow used: 7.64 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.13403 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.11E-006  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.914E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  7.64  (KowWin est)
  Log Kaw used:  -3.602  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.242
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1628
   Biowin2 (Non-Linear Model)     :   0.0012
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8329  (months      )
   Biowin4 (Primary Survey Model) :   2.9359  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2041
   Biowin6 (MITI Non-Linear Model):   0.0129
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.3560
 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):  1.22E-007 Pa (9.17E-010 mm Hg)
  Log Koa (Koawin est  ): 11.242
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  24.5 
       Octanol/air (Koa) model:  0.0429 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  0.774 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 134.6435 E-12 cm3/molecule-sec
      Half-Life =     0.079 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.953 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.393750 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.720 Hrs
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  6.366E+004
      Log Koc:  4.804 

 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 = 3.930 (BCF = 8504)
       log Kow used: 7.64 (estimated)

 Volatilization from Water:
    Henry LC:  6.11E-006 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      194.3  hours   (8.097 days)
    Half-Life from Model Lake :       2288  hours   (95.34 days)

 Removal In Wastewater Treatment:
    Total removal:              93.99  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.21  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       0.012           1.26         1000       
   Water     1.42            1.44e+003    1000       
   Soil      30.7            2.88e+003    1000       
   Sediment  67.9            1.3e+004     0          
     Persistence Time: 4.72e+003 hr




                    

Click to predict properties on the Chemicalize site






Advertisement