ChemSpider 2D Image | Treprostinil | C23H34O5

Treprostinil

  • Molecular FormulaC23H34O5
  • Average mass390.513 Da
  • Monoisotopic mass390.240631 Da
  • ChemSpider ID5293353
  • defined stereocentres - 5 of 5 defined stereocentres


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

({(1R,2R,3aS,9aS)-2-Hydroxy-1-[(3S)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yl}oxy)acetic acid [ACD/IUPAC Name]
({(1R,2R,3aS,9aS)-2-Hydroxy-1-[(3S)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalin-5-yl}oxy)essigsäure [German] [ACD/IUPAC Name]
[(1R,2R,3aS,9aS)-2-hydroxy-1-((3S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cylopent[b]naphthalen-5-yl]oxy]acetate
2-[[(1R,2R,3aS,9aS)-2,3,4,9,9a-hexahydro-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]inden-5-yl]oxy]-acetic acid
8170
81846-19-7 [RN]
acetic acid, [[(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]inden-5-yl]oxy]-
Acetic acid, 2-[[(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]inden-5-yl]oxy]- [ACD/Index Name]
Acide ({(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphtalén-5-yl}oxy)acétique [French] [ACD/IUPAC Name]
MFCD00888847
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

15AU81 [DBID]
LRX-15 [DBID]
UT-15 [DBID]
CCRIS 4693 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      B01AC21 Wikidata Q3495231
    • Bio Activity:

      7-TM Receptors Tocris Bioscience 5349
      Potent prostacyclin (PGI2) analog Tocris Bioscience 5349
      Potent prostacyclin (PGI2) analog (EC50 values are 0.6, 1.9 and 6.2 nM at DP1, IP and EP2 receptors respectively). Causes vasodilation of human pulmonary arteries and inhibits NF?B nuclear translocati on in human alveolar macrophages in vitro. Tocris Bioscience 5349
      Potent prostacyclin (PGI2) analog (EC50 values are 0.6, 1.9 and 6.2 nM at DP1, IP and EP2 receptors respectively). Causes vasodilation of human pulmonary arteries and inhibits NF?B nuclear translocation in human alveolar macrophages in vitro. Tocris Bioscience 5349
      Potent prostacyclin (PGI2) analog (EC50 values are 0.6, 1.9 and 6.2 nM at DP1, IP and EP2 receptors respectively). Causes vasodilation of human pulmonary arteries and inhibits NFkappaB nuclear translocation in human alveolar macrophages in vitro. Tocris Bioscience 5349
      Prostanoid Receptors Tocris Bioscience 5349

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

Density: 1.2±0.1 g/cm3
Boiling Point: 587.1±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 92.2±3.0 kJ/mol
Flash Point: 199.3±23.6 °C
Index of Refraction: 1.554
Molar Refractivity: 108.0±0.3 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 10
#Rule of 5 Violations: 0
ACD/LogP: 4.40
ACD/LogD (pH 5.5): 2.60
ACD/BCF (pH 5.5): 15.71
ACD/KOC (pH 5.5): 55.68
ACD/LogD (pH 7.4): 1.28
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 2.63
Polar Surface Area: 87 Å2
Polarizability: 42.8±0.5 10-24cm3
Surface Tension: 47.3±3.0 dyne/cm
Molar Volume: 337.1±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) =  5.01

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  537.34  (Adapted Stein & Brown method)
    Melting Pt (deg C):  230.04  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.41E-014  (Modified Grain method)
    Subcooled liquid VP: 3.86E-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):  0.4606
       log Kow used: 5.01 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.1998 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.11E-013  atm-m3/mole
   Group Method:   7.73E-017  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  2.689E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.01  (KowWin est)
  Log Kaw used:  -11.064  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.074
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.3015
   Biowin2 (Non-Linear Model)     :   0.9963
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1112  (weeks       )
   Biowin4 (Primary Survey Model) :   4.1379  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5274
   Biowin6 (MITI Non-Linear Model):   0.1785
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5931
 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):  5.15E-010 Pa (3.86E-012 mm Hg)
  Log Koa (Koawin est  ): 16.074
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.83E+003 
       Octanol/air (Koa) model:  2.91E+003 
   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 = 105.5346 E-12 cm3/molecule-sec
      Half-Life =     0.101 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.216 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  231
      Log Koc:  2.364 

 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 = 0.750 (BCF = 5.623)
       log Kow used: 5.01 (estimated)

 Volatilization from Water:
    Henry LC:  2.11E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.483E+009  hours   (2.285E+008 days)
    Half-Life from Model Lake : 5.982E+010  hours   (2.492E+009 days)

 Removal In Wastewater Treatment:
    Total removal:              78.02  percent
    Total biodegradation:        0.68  percent
    Total sludge adsorption:    77.34  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       0.147           2.43         1000       
   Water     16.8            360          1000       
   Soil      63.5            720          1000       
   Sediment  19.6            3.24e+003    0          
     Persistence Time: 632 hr




                    

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