ChemSpider 2D Image | (3aR,4R,5R,6aS)-tilsuprost | C20H33NO4S

(3aR,4R,5R,6aS)-tilsuprost

  • Molecular FormulaC20H33NO4S
  • Average mass383.545 Da
  • Monoisotopic mass383.213043 Da
  • ChemSpider ID4947239
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 5 defined stereocentres


More details:






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

(3aR,4R,5R,6aS)-tilsuprost
4-({(3aR,4R,5R,6aS)-5-Hydroxy-4-[(1E,3S)-3-hydroxy-1-octén-1-yl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]pyrrol-2-yl}sulfanyl)butanoate de méthyle [French] [ACD/IUPAC Name]
Butanoic acid, 4-[[(3aR,4R,5R,6aS)-3,3a,4,5,6,6a-hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]cyclopenta[b]pyrrol-2-yl]thio]-, methyl ester [ACD/Index Name]
Methyl 4-(((3aR,4R,5R,6aS)-3,3a,4,5,6,6a-hexahydro-5-hydroxy-4-((E)-(3S)-3-hydroxy-1-octenyl)cyclopenta[b]pyrrol-2-yl)thio)butyrate
Methyl 4-({(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]pyrrol-2-yl}sulfanyl)butanoate [ACD/IUPAC Name]
Methyl-4-({(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]pyrrol-2-yl}sulfanyl)butanoat [German] [ACD/IUPAC Name]
tilsuprost [INN]
tilsuprost [Spanish] [INN]
tilsuprost [French] [INN]
tilsuprostum [Latin] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Hoe 892 [DBID]
Hoe-892 [DBID]

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

Density: 1.2±0.1 g/cm3
Boiling Point: 506.9±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.0 mmHg at 25°C
Enthalpy of Vaporization: 89.4±6.0 kJ/mol
Flash Point: 260.3±30.1 °C
Index of Refraction: 1.579
Molar Refractivity: 104.1±0.5 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 12
#Rule of 5 Violations: 0
ACD/LogP: 2.04
ACD/LogD (pH 5.5): 2.33
ACD/BCF (pH 5.5): 20.81
ACD/KOC (pH 5.5): 166.55
ACD/LogD (pH 7.4): 3.22
ACD/BCF (pH 7.4): 160.06
ACD/KOC (pH 7.4): 1280.80
Polar Surface Area: 104 Å2
Polarizability: 41.3±0.5 10-24cm3
Surface Tension: 44.1±7.0 dyne/cm
Molar Volume: 313.3±7.0 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) =  5.49

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  488.75  (Adapted Stein & Brown method)
    Melting Pt (deg C):  202.47  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.82E-012  (Modified Grain method)
    Subcooled liquid VP: 1.37E-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):  0.07996
       log Kow used: 5.49 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.3963 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.97E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.149E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.49  (KowWin est)
  Log Kaw used:  -10.094  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.584
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1650
   Biowin2 (Non-Linear Model)     :   0.9967
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1101  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0513  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6348
   Biowin6 (MITI Non-Linear Model):   0.2433
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5834
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  1.83E-008 Pa (1.37E-010 mm Hg)
  Log Koa (Koawin est  ): 15.584
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  164 
       Octanol/air (Koa) model:  942 
   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 =  96.1770 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 103.7770 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.335 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.237 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    :  883.9
      Log Koc:  2.946 

 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 = 2.524 (BCF = 334.1)
       log Kow used: 5.49 (estimated)

 Volatilization from Water:
    Henry LC:  1.97E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  5.82E+008  hours   (2.425E+007 days)
    Half-Life from Model Lake :  6.35E+009  hours   (2.646E+008 days)

 Removal In Wastewater Treatment:
    Total removal:              88.15  percent
    Total biodegradation:        0.74  percent
    Total sludge adsorption:    87.41  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       0.0541          1.18         1000       
   Water     11.7            360          1000       
   Soil      52              720          1000       
   Sediment  36.3            3.24e+003    0          
     Persistence Time: 800 hr




                    

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