ChemSpider 2D Image | (1S,3R,5Z,7E,23S)-23-(2-Hydroxy-2-methylpropyl)-20,24-epoxy-9,10-secochola-5,7,10-triene-1,3-diol | C28H44O4

(1S,3R,5Z,7E,23S)-23-(2-Hydroxy-2-methylpropyl)-20,24-epoxy-9,10-secochola-5,7,10-triene-1,3-diol

  • Molecular FormulaC28H44O4
  • Average mass444.647 Da
  • Monoisotopic mass444.323975 Da
  • ChemSpider ID13171758

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 7 of 7 defined stereocentres

More details:

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

(1S,3R,5Z,7E,14β,17α)-17-[(2S,4S)-4-(2-hydroxy-2-methylpropyl)-2-methyltetrahydrofuran-2-yl]-9,10-secoandrosta-5,7,10-triene-1,3-diol
(1S,3R,5Z,7E,23S)-23-(2-Hydroxy-2-methylpropyl)-20,24-epoxy-9,10-secochola-5,7,10-trien-1,3-diol [German] [ACD/IUPAC Name]
(1S,3R,5Z,7E,23S)-23-(2-Hydroxy-2-methylpropyl)-20,24-epoxy-9,10-secochola-5,7,10-triene-1,3-diol [ACD/IUPAC Name]
(1S,3R,5Z,7E,23S)-23-(2-Hydroxy-2-méthylpropyl)-20,24-époxy-9,10-sécochola-5,7,10-triène-1,3-diol [French] [ACD/IUPAC Name]
1,3-Cyclohexanediol, 4-methylene-5-[(2E)-2-[(1S,3aS,7aS)-octahydro-7a-methyl-1-[(2S,4S)-tetrahydro-4-(2-hydroxy-2-methylpropyl)-2-methyl-2-furanyl]-4H-inden-4-ylidene]ethylidene]-, (1R,3S,5Z)- [ACD/Index Name]
AMCR277A
COV
  • Miscellaneous

    • Chemical Class:

      A hydroxycalciol that is calcitriol which has undergone formal oxidative coupling at positions 20 and 23 to the hydroxy group and methyl group, respectively, of methanol to afford the corresponding ox olane ring (the 20<stereo>S</stereo>,23<stereo>S</stereo> stereoisomer). It is a superagonist of the vitamin D nuclear receptor in vitro, but is as calcemic in vivo as the natural ligand. ChEBI CHEBI:139026
      A hydroxycalciol that is calcitriol which has undergone formal oxidative coupling at positions 20 and 23 to the hydroxy group and methyl group, respectively, of methanol to afford the corresponding ox olane ring (the 20S,23S stereoisomer). It is a superagonist of the vitamin D nuclear receptor in vitro, but is as calcemic in vivo as the natural ligand. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:139026

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

Density: 1.1±0.1 g/cm3
Boiling Point: 595.1±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.8 mmHg at 25°C
Enthalpy of Vaporization: 101.8±6.0 kJ/mol
Flash Point: 313.7±30.1 °C
Index of Refraction: 1.564
Molar Refractivity: 128.7±0.4 cm3
#H bond acceptors: 4
#H bond donors: 3
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 4.42
ACD/LogD (pH 5.5): 4.64
ACD/BCF (pH 5.5): 1997.02
ACD/KOC (pH 5.5): 8016.97
ACD/LogD (pH 7.4): 4.64
ACD/BCF (pH 7.4): 1997.02
ACD/KOC (pH 7.4): 8016.97
Polar Surface Area: 70 Å2
Polarizability: 51.0±0.5 10-24cm3
Surface Tension: 47.2±5.0 dyne/cm
Molar Volume: 395.6±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) =  6.62

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  538.37  (Adapted Stein & Brown method)
    Melting Pt (deg C):  230.52  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.38E-015  (Modified Grain method)
    Subcooled liquid VP: 1.03E-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):  0.00361
       log Kow used: 6.62 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3.1578 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.00E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.034E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.62  (KowWin est)
  Log Kaw used:  -8.087  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.707
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.0458
   Biowin2 (Non-Linear Model)     :   0.0001
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8914  (months      )
   Biowin4 (Primary Survey Model) :   2.9950  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2315
   Biowin6 (MITI Non-Linear Model):   0.0060
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.6276
 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):  1.37E-010 Pa (1.03E-012 mm Hg)
  Log Koa (Koawin est  ): 14.707
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.18E+004 
       Octanol/air (Koa) model:  125 
   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 = 320.2079 E-12 cm3/molecule-sec
      Half-Life =     0.033 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    24.050 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =   223.583740 E-17 cm3/molecule-sec
      Half-Life =     0.005 Days (at 7E11 mol/cm3)
      Half-Life =      7.381 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    :  1.774E+004
      Log Koc:  4.249 

 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 = 4.394 (BCF = 2.476e+004)
       log Kow used: 6.62 (estimated)

 Volatilization from Water:
    Henry LC:  2E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.173E+006  hours   (2.572E+005 days)
    Half-Life from Model Lake : 6.734E+007  hours   (2.806E+006 days)

 Removal In Wastewater Treatment:
    Total removal:              93.58  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    92.80  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       0.00116         0.107        1000       
   Water     1.83            1.44e+003    1000       
   Soil      31.7            2.88e+003    1000       
   Sediment  66.5            1.3e+004     0          
     Persistence Time: 4.39e+003 hr

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