ChemSpider 2D Image | (11R,16S)-misoprostol | C22H38O5

(11R,16S)-misoprostol

  • Molecular FormulaC22H38O5
  • Average mass382.534 Da
  • Monoisotopic mass382.271912 Da
  • ChemSpider ID8061946
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 4 of 4 defined stereocentres


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(11R,16S)-misoprostol
(11α,13E,16S)-11,16-Dihydroxy-16-méthyl-9-oxoprost-13-én-1-oate de méthyle [French] [ACD/IUPAC Name]
Methyl (11α,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [ACD/IUPAC Name]
Methyl-(11α,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oat [German] [ACD/IUPAC Name]
Prost-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, methyl ester, (11α,13E,16S)- [ACD/Index Name]
(16S)-15-deoxy--16-hydroxy-16-methyl-PGE1 methyl ester
59122-46-2 [RN]
7-[(1R,2R,3R)-3-hydroxy-2-[(E,4S)-4-hydroxy-4-methyl-oct-1-enyl]-5-keto-cyclopentyl]enanthic acid methyl ester
7-[(1R,2R,3R)-3-hydroxy-2-[(E,4S)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoic acid methyl ester
methyl 11R,16S-dihydroxy-16-methyl-9-oxoprost-13E-en-1-oate
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:63695 [DBID]
  • Miscellaneous
    • Chemical Class:

      A methyl (13<stereo>E</stereo>)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate that has 8<stereo>S</stereo>,11<stereo>S</stereo>,12<stereo>S</stereo>,16<stereo>R</stereo>-configuration. It is the p harmacologically active diastereoisomeric component of misoprostol. ChEBI CHEBI:63695

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

Density: 1.1±0.1 g/cm3
Boiling Point: 497.3±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.9 mmHg at 25°C
Enthalpy of Vaporization: 88.1±6.0 kJ/mol
Flash Point: 160.4±22.2 °C
Index of Refraction: 1.525
Molar Refractivity: 108.7±0.3 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 14
#Rule of 5 Violations: 0
ACD/LogP: 2.91
ACD/LogD (pH 5.5): 3.28
ACD/BCF (pH 5.5): 182.04
ACD/KOC (pH 5.5): 1443.58
ACD/LogD (pH 7.4): 3.28
ACD/BCF (pH 7.4): 182.04
ACD/KOC (pH 7.4): 1443.58
Polar Surface Area: 84 Å2
Polarizability: 43.1±0.5 10-24cm3
Surface Tension: 46.1±3.0 dyne/cm
Molar Volume: 354.8±3.0 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) =  4.47

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  479.87  (Adapted Stein & Brown method)
    Melting Pt (deg C):  192.53  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.54E-012  (Modified Grain method)
    Subcooled liquid VP: 2.6E-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):  0.5951
       log Kow used: 4.47 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  12.878 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.56E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.840E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.47  (KowWin est)
  Log Kaw used:  -9.510  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.980
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8297
   Biowin2 (Non-Linear Model)     :   0.9199
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7177  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7476  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8291
   Biowin6 (MITI Non-Linear Model):   0.6043
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0307
 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):  3.47E-008 Pa (2.6E-010 mm Hg)
  Log Koa (Koawin est  ): 13.980
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  86.5 
       Octanol/air (Koa) model:  23.4 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 107.3090 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 114.9090 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.196 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.117 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    13.000000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    20.000000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     2.116 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.375 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    :  68.5
      Log Koc:  1.836 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  6.634E-002  L/mol-sec
  Kb Half-Life at pH 8:     120.916  days   
  Kb Half-Life at pH 7:       3.310  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.744 (BCF = 55.4)
       log Kow used: 4.47 (estimated)

 Volatilization from Water:
    Henry LC:  7.56E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.515E+008  hours   (6.311E+006 days)
    Half-Life from Model Lake : 1.652E+009  hours   (6.885E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              54.44  percent
    Total biodegradation:        0.51  percent
    Total sludge adsorption:    53.93  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       0.0354          1.12         1000       
   Water     14.3            900          1000       
   Soil      75.7            1.8e+003     1000       
   Sediment  10              8.1e+003     0          
     Persistence Time: 1.29e+003 hr




                    

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