ChemSpider 2D Image | Limaprost | C22H36O5

Limaprost

  • Molecular FormulaC22H36O5
  • Average mass380.518 Da
  • Monoisotopic mass380.256287 Da
  • ChemSpider ID4942859
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 5 defined stereocentres


More details:



Featured data source



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

(2E)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonen-1-yl]-5-oxocyclopentyl}-2-heptenoic acid [ACD/IUPAC Name]
(2E)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonen-1-yl]-5-oxocyclopentyl}-2-heptensäure [German] [ACD/IUPAC Name]
(2E)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-5-oxocyclopentyl}hept-2-enoic acid (non-preferred name)
(2E,11a,13E,15S,17S)-11,15-Dihydroxy-17,20-dimethyl-9-oxoprosta-2,13-dien-1-oic Acid
(E)-7-((1R,2R,3R)-3-Hydroxy-2-((E)-(3S,5S)-3-hydroxy-5-methyl-1-nonenyl)-5-oxocyclopentyl)-2-heptenoic acid
11α,15S-DIHYDROXY-17S,20-DIMETHYL-9-OXO-PROSTA-2E,13E-DIEN-1-OIC ACID
17S-Methyl-w-homo-trans-D2-PGE1
17α,20-dimethyl-δ2-pge1
5899
74397-12-9 [RN]
More...

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

D02722 [DBID]
ONO 1206 [DBID]
OP 1206 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 099415
    • Bio Activity:

      Limaprost(OP1206) is a PGE1 analog and potent platelet adhesion inhibitor. MedChem Express
      Limaprost(OP1206) is a PGE1 analog and potent platelet adhesion inhibitor.; Target: Others; Limaprost, an alprostadil (prostaglandin E1) analogue, is a vasodilator that increases blood flow and inhibits platelet aggregation. MedChem Express HY-B0683
      Limaprost(OP1206) is a PGE1 analog and potent platelet adhesion inhibitor.;Target: Limaprost, an alprostadil (prostaglandin E1) analogue, is a vasodilator that increases blood flow and inhibits platelet aggregation. Limaprost is a n analog of PGE1 with structural modifications intended to give a prolonged half-life and greater potency. It is orally active in both guinea pigs and rats at doses of 100 mg/kg as an inhibitor of ADP and collagen induced platelet aggregation. It is 10-1,000 times more potent than PGE1 as a platelet adhesive inhibitor, measured in vitro. Intra-coronary injection (100 ng/kg) or intravenous injection (3 mg/kg) in anesthetized dogs causes vasodilation and increased coronary blood flow by 60-80%. Significant hypotensive effects were seen at 100 and 300 mg/kg orally in rats [1]. MedChem Express HY-B0683
      Others MedChem Express HY-B0683

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

Density: 1.1±0.1 g/cm3
Boiling Point: 550.6±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.4 mmHg at 25°C
Enthalpy of Vaporization: 95.5±6.0 kJ/mol
Flash Point: 300.9±26.6 °C
Index of Refraction: 1.551
Molar Refractivity: 108.5±0.3 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 13
#Rule of 5 Violations: 0
ACD/LogP: 3.15
ACD/LogD (pH 5.5): 2.36
ACD/BCF (pH 5.5): 23.34
ACD/KOC (pH 5.5): 196.56
ACD/LogD (pH 7.4): 0.56
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 3.15
Polar Surface Area: 95 Å2
Polarizability: 43.0±0.5 10-24cm3
Surface Tension: 50.8±3.0 dyne/cm
Molar Volume: 340.2±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) =  4.43

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  531.13  (Adapted Stein & Brown method)
    Melting Pt (deg C):  227.14  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.14E-014  (Modified Grain method)
    Subcooled liquid VP: 6.1E-012 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):  1.665
       log Kow used: 4.43 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  15.235 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 :   1.47E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.245E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.43  (KowWin est)
  Log Kaw used:  -12.221  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.651
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0718
   Biowin2 (Non-Linear Model)     :   0.8670
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.3187  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.1900  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5779
   Biowin6 (MITI Non-Linear Model):   0.2234
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0001
 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):  8.13E-010 Pa (6.1E-012 mm Hg)
  Log Koa (Koawin est  ): 16.651
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.69E+003 
       Octanol/air (Koa) model:  1.1E+004 
   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 = 131.1666 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 141.4266 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.979 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.908 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    13.568750 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    21.137501 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     2.027 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.301 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   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    :  26.06
      Log Koc:  1.416 

 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: 4.43 (estimated)

 Volatilization from Water:
    Henry LC:  1.47E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.769E+010  hours   (3.237E+009 days)
    Half-Life from Model Lake : 8.476E+011  hours   (3.532E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              52.30  percent
    Total biodegradation:        0.49  percent
    Total sludge adsorption:    51.80  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       0.0568          0.996        1000       
   Water     20.3            208          1000       
   Soil      75.4            416          1000       
   Sediment  4.18            1.87e+003    0          
     Persistence Time: 392 hr




                    

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