ChemSpider 2D Image | (-)-Prostaglandin E2 | C20H32O5

(-)-Prostaglandin E2

  • Molecular FormulaC20H32O5
  • Average mass352.465 Da
  • Monoisotopic mass352.224976 Da
  • ChemSpider ID4444059
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 4 of 4 defined stereocentres


More details:



Featured data source



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(-)-Prostaglandin E2
(5Z)-7-{(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl}hept-5-enoic acid
(5Z)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl}hept-5-ensäure [German]
(5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic Acid
(5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid [ACD/IUPAC Name]
(5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-säure [German] [ACD/IUPAC Name]
206-656-6 [EINECS]
3075
363-24-6 [RN]
acide (5Z)-7-{(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-én-1-yl]-5-oxocyclopentyl}hept-5-énoïque [French]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS003352 [DBID]
AIDS-003352 [DBID]
AIDS166064 [DBID]
AIDS-166064 [DBID]
C00584 [DBID]
CHEBI:15551 [DBID]
D00079 [DBID]
LMFA03010003 [DBID]
NSC 165560 [DBID]
NSC 196514 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      G02AD02 Wikidata Q416554
      IRRITANT Matrix Scientific 090192
    • Chemical Class:

      Prostaglandin F<smallsub>2<greek>alpha</greek></smallsub> in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E<smallsub>2</smallsub> is the most comm on and most biologically potent of mammalian prostaglandins. ChEBI CHEBI:15551
    • Bio Activity:

      7-TM Receptors Tocris Bioscience 2296
      Endogenous prostaglandin and primary product of arachidonic acid/cyclooxygenase pathway. Binds with high affinity to EP1, EP2, EP3 and EP4 receptors (Kd values range between ~ 1 - 10 nM). Influences a wide range of processes including inflammation, smooth muscle relaxation, fertility and gastric mucosal integrity. Regulates vertebrate hematopoietic stem cell (HSC) homeostasis. Tocris Bioscience 2296
      Endogenous prostaglandin and primary product of arachidonic acid/cyclooxygenase pathway. Binds with high affinity to EP1, EP2, EP3 and EP4 receptors (Kd values range between ~ 1 - 10 nM). Influences a wide range of processes including inflammation, smooth muscle relaxation, fertility and gastric mucosal integrity. Regulates vertebrate hematopoietic stem cell (HSC) homeostasis. Tocris Bioscience 2296
      Major endogenous prostanoid Tocris Bioscience 2296
      Prostanoid Receptors Tocris Bioscience 2296

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

Density: 1.1±0.1 g/cm3
Boiling Point: 530.1±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.2 mmHg at 25°C
Enthalpy of Vaporization: 92.6±6.0 kJ/mol
Flash Point: 288.5±26.6 °C
Index of Refraction: 1.561
Molar Refractivity: 99.3±0.3 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 12
#Rule of 5 Violations: 0
ACD/LogP: 1.88
ACD/LogD (pH 5.5): 1.67
ACD/BCF (pH 5.5): 6.98
ACD/KOC (pH 5.5): 81.89
ACD/LogD (pH 7.4): -0.13
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.31
Polar Surface Area: 95 Å2
Polarizability: 39.4±0.5 10-24cm3
Surface Tension: 53.6±3.0 dyne/cm
Molar Volume: 306.8±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) =  3.52
    Log Kow (Exper. database match) =  2.82
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  514.92  (Adapted Stein & Brown method)
    Melting Pt (deg C):  219.57  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.13E-012  (Modified Grain method)
    MP  (exp database):  67 deg C
    Subcooled liquid VP: 2.01E-011 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):  58.05
       log Kow used: 2.82 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  519.42 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.56E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.495E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.82  (exp database)
  Log Kaw used:  -12.195  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.015
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0852
   Biowin2 (Non-Linear Model)     :   0.9066
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.3807  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.2305  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7116
   Biowin6 (MITI Non-Linear Model):   0.4120
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2455
 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):  2.68E-009 Pa (2.01E-011 mm Hg)
  Log Koa (Koawin est  ): 15.015
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.12E+003 
       Octanol/air (Koa) model:  254 
   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 = 163.3351 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 178.5351 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.786 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.719 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    26.000000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    40.000000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     1.058 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     0.688 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    :  10
      Log Koc:  1.000 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 2.82 (expkow database)

 Volatilization from Water:
    Henry LC:  1.56E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.046E+010  hours   (2.936E+009 days)
    Half-Life from Model Lake : 7.687E+011  hours   (3.203E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               4.42  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     4.31  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       0.000606        0.632        1000       
   Water     19.1            208          1000       
   Soil      80.7            416          1000       
   Sediment  0.181           1.87e+003    0          
     Persistence Time: 459 hr




                    

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