ChemSpider 2D Image | Misoprostol | C22H38O5

Misoprostol

  • Molecular FormulaC22H38O5
  • Average mass382.534 Da
  • Monoisotopic mass382.271912 Da
  • ChemSpider ID4445541
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 3 of 4 defined stereocentres


More details:






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

(11a,13E)-(±)-11,16-Dihydroxy-16-methyl-9-oxoprost-13-en-1-oic Acid Methyl Ester
(11α,13E)-11,16-Dihydroxy-16-méthyl-9-oxoprost-13-én-1-oate de méthyle [French] [ACD/IUPAC Name]
5154
59122-46-2 [RN]
7-{(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-méthyloct-1-én-1-yl]-5-oxocyclopentyl}heptanoate de méthyle [French]
Methyl (11α,13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [ACD/IUPAC Name]
methyl 7-{(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl}heptanoate
Methyl-(11α,13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oat [German] [ACD/IUPAC Name]
Methyl-7-{(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl}heptanoat
misoprostol [Spanish] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

0E43V0BB57 [DBID]
HSDB 3573 [DBID]
SC 29333 [DBID]
UNII:0E43V0BB57 [DBID]
BRN 4155643 [DBID]
CCRIS 6859 [DBID]
D00419 [DBID]
M6807_SIGMA [DBID]
MLS000028863 [DBID]
PubChem Substance ID 329831176 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      A02BB01 Wikidata Q416025
      Danger Biosynth Q-201409
      G02AD06 Wikidata Q416025
      GHS06; GHS08 Biosynth Q-201409
      H301; H360 Biosynth Q-201409
      P201; P301+P310; P308+P313 Biosynth Q-201409
    • Target Organs:

      Estrogen/Progestogen Receptor agonist TargetMol T2573
    • Therapeutical Effect:

      antiulcer Microsource [01505616]
    • Drug Status:

      USAN, INN, BAN, JAN Microsource [01505616]
    • Compound Source:

      semisynthetic; SC-29333 Microsource [01505616]
    • Bio Activity:

      7-TM Receptors Tocris Bioscience 2297
      Cytoprotective PGE1 analog Tocris Bioscience 2297
      Cytoprotective prostaglandin E1 analog that displays agonist activity at EP receptors. Ki values are 120, 250, 67 and 67 nM at cloned mouse EP1, EP2, EP3 and EP4 receptors respectively. Prevents NSAID -induced gastric ulceration. Tocris Bioscience 2297
      Cytoprotective prostaglandin E1 analog that displays agonist activity at EP receptors. Ki values are 120, 250, 67 and 67 nM at cloned mouse EP1, EP2, EP3 and EP4 receptors respectively. Prevents NSAID-induced gastric ulceration. Tocris Bioscience 2297
      Endocrinology/ Hormones TargetMol T2573
      Estrogen/progestogen Receptor TargetMol T2573
      GPCR/G protein MedChem Express HY-B0610
      GPCR/G protein; MedChem Express HY-B0610
      Misoprostol(SC29333) is a synthetic prostaglandin E1 (PGE1) analog that is used to prevent gastric ulcers, to treat missed miscarriage, to induce labor, and to induce abortion. MedChem Express
      Misoprostol(SC29333) is a synthetic prostaglandin E1 (PGE1) analog that is used to prevent gastric ulcers, to treat missed miscarriage, to induce labor, and to induce abortion.; Target: Prostaglandin Receptor; Misoprostol is a synthetic analog of natural prostaglandin E1. MedChem Express HY-B0610
      Misoprostol(SC29333) is a synthetic prostaglandin E1 (PGE1) analog that is used to prevent gastric ulcers, to treat missed miscarriage, to induce labor, and to induce abortion.;Target: Prostaglandin ReceptorMisoprostol is a synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties. Misoprostol seems to inhibit gastric acid secretion by a direct action on the parietal cells through binding to the prostaglandin receptor. Administration of misoprostol to EP3+/+ and EP3-/- mice showed similar levels of infarct rescue, indicating that misoprostol protection was not mediated through the EP3 receptor. Taken together, these findings suggest a novel function for misoprostol as a protective agent in cerebral ischemia acting via the PGE(2) EP2 and/or EP4 receptors [1, 2]. MedChem Express HY-B0610
      Prostaglandin Receptor MedChem Express HY-B0610
      Prostanoid Receptors Tocris Bioscience 2297

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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