ChemSpider 2D Image | Iloprost | C22H32O4

Iloprost

  • Molecular FormulaC22H32O4
  • Average mass360.487 Da
  • Monoisotopic mass360.230072 Da
  • ChemSpider ID4470703
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 6 defined stereocentres


More details:



Featured data source



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

(5E)-5-[(3aS,4R,5R,6aS)-5-Hydroxy-4-[(1E,3S)-3-hydroxy-4-methyl-1-octen-6-in-1-yl]hexahydro-2(1H)-pentalenyliden]pentansäure [German] [ACD/IUPAC Name]
(5E)-5-[(3aS,4R,5R,6aS)-5-Hydroxy-4-[(1E,3S)-3-hydroxy-4-methyl-1-octen-6-yn-1-yl]hexahydro-2(1H)-pentalenylidene]pentanoic acid [ACD/IUPAC Name]
(5E)-5-[(3aS,4R,5R,6aS)-5-Hydroxy-4-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]hexahydropentalen-2(1H)-ylidene]pentanoic acid
78919-13-8 [RN]
Acide (5E)-5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-méthyl-1-octén-6-yn-1-yl]hexahydro-2(1H)-pentalénylidène]pentanoïque [French] [ACD/IUPAC Name]
CILOPROST
iloprostum [Latin] [INN]
Pentanoic acid, 5-[(3aS,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyl-1-octen-6-yn-1-yl]-2(1H)-pentalenylidene]-, (5E)- [ACD/Index Name]
UNII:JED5K35YGL
More...

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

CHEBI:63916 [DBID]
D02721 [DBID]
E-1030 [DBID]
SH-401 [DBID]
UN1231 [DBID]
ZK 36374 [DBID]
ZK-36374 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      B01AC11 Wikidata Q20817139
    • Chemical Class:

      A carbobicyclic compound that is prostaglandin I<smallsub>2</smallsub> in which the endocyclic oxygen is replaced by a methylene group and in which the (1<stereo>E</stereo>,3<stereo>S</stereo>)-3-hydr oxyoct-1-en-1-yl side chain is replaced by a (3<stereo>R</stereo>)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl group. A synthetic analogue of prostacyclin, it is used as the trometamol salt (generally by int ravenous infusion) for the treatment of peripheral vascular disease and pulmonary hypertension. ChEBI CHEBI:63916
    • Bio Activity:

      7-TM Receptors Tocris Bioscience 2038
      GPCR/G protein; MedChem Express HY-A0096
      Iloprost (ZK 36374) is a synthetic analogue of prostacyclin PGI2.;Target: ;Iloprost is a stable prostacyclin analog commonly employed in the treatment of peripheral vascular disease and also indicated in the treatment of patients affected by systemic sclerosis (SSc) in the presence of severe Raynaud's phenomenon (RP). [1] Iloprost dilates systemic and pulmonary arterial vascularbeds. Iloprost also affects platelet aggregation but the relevance of this effect to the treatment of pulmonary hypertension is unknown. The two diastereoisomers of iloprost differ in their potency in dilating blood vessels, with the 4S isomer substantially more potent than the 4R isomer.[2] Iloprost is a stable carbacyclin derivative of prostacyclin, was studied during electrically-induced coronary artery thrombosis in the open chest anesthetized pig. Infusion of ZK 36374 (100 ng/kg/min, n = 6) had no effect on heart rate and cardiac output, but caused a 20% reduction in mean arterial blood pressure by peri MedChem Express HY-A0096
      Prostacyclin (PGI2) analog Tocris Bioscience 2038
      Prostacyclin (PGI2) analog that binds with high affinity to IP, EP1 and EP3 receptors (Ki values are 11, 11, 56, 284, 619, 1035, 1870 and 6487 nM for IP, EP1, EP3, EP4, FP, DP, EP2 and TP receptors re spectively). Inhibits platelet aggregation induced by collagen, thrombin and ADP (IC50 values are 0.24, 0.71 and 1.07 nM respectively). Tocris Bioscience 2038
      Prostacyclin (PGI2) analog that binds with high affinity to IP, EP1 and EP3 receptors (Ki values are 11, 11, 56, 284, 619, 1035, 1870 and 6487 nM for IP, EP1, EP3, EP4, FP, DP, EP2 and TP receptors respectively). Inhibits platelet aggregation induced by collagen, thrombin and ADP (IC50 values are 0.24, 0.71 and 1.07 nM respectively). Tocris Bioscience 2038
      Prostaglandin Receptor MedChem Express HY-A0096
      Prostanoid Receptors Tocris Bioscience 2038

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

Density: 1.2±0.1 g/cm3
Boiling Point: 539.2±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.3 mmHg at 25°C
Enthalpy of Vaporization: 93.9±6.0 kJ/mol
Flash Point: 294.0±26.6 °C
Index of Refraction: 1.629
Molar Refractivity: 105.9±0.3 cm3
#H bond acceptors: 4
#H bond donors: 3
#Freely Rotating Bonds: 9
#Rule of 5 Violations: 0
ACD/LogP: 2.94
ACD/LogD (pH 5.5): 2.79
ACD/BCF (pH 5.5): 49.60
ACD/KOC (pH 5.5): 335.60
ACD/LogD (pH 7.4): 0.99
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 5.37
Polar Surface Area: 78 Å2
Polarizability: 42.0±0.5 10-24cm3
Surface Tension: 64.9±3.0 dyne/cm
Molar Volume: 297.8±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) =  4.95

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  506.75  (Adapted Stein & Brown method)
    Melting Pt (deg C):  215.75  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.4E-013  (Modified Grain method)
    Subcooled liquid VP: 3.67E-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):  0.793
       log Kow used: 4.95 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  16.25 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.35E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.034E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.95  (KowWin est)
  Log Kaw used:  -10.017  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.967
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9661
   Biowin2 (Non-Linear Model)     :   0.6832
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0871  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9721  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3678
   Biowin6 (MITI Non-Linear Model):   0.0520
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4787
 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):  4.89E-009 Pa (3.67E-011 mm Hg)
  Log Koa (Koawin est  ): 14.967
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  613 
       Octanol/air (Koa) model:  228 
   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 = 201.0474 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 208.6474 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.638 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.615 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    56.002998 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    63.002998 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     0.491 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     0.437 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    :  273.2
      Log Koc:  2.436 

 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: 4.95 (estimated)

 Volatilization from Water:
    Henry LC:  2.35E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  4.73E+008  hours   (1.971E+007 days)
    Half-Life from Model Lake :  5.16E+009  hours   (2.15E+008 days)

 Removal In Wastewater Treatment:
    Total removal:              76.05  percent
    Total biodegradation:        0.67  percent
    Total sludge adsorption:    75.39  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       0.0289          0.355        1000       
   Water     18.5            360          1000       
   Soil      62.4            720          1000       
   Sediment  19              3.24e+003    0          
     Persistence Time: 570 hr




                    

Click to predict properties on the Chemicalize site





Feedback Form