ChemSpider 2D Image | (+)-Fluprostenol | C23H29F3O6

(+)-Fluprostenol

  • Molecular FormulaC23H29F3O6
  • Average mass458.468 Da
  • Monoisotopic mass458.191620 Da
  • ChemSpider ID4470630

  • 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

(+)-Fluprostenol
(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-{(1E,3R)-3-hydroxy-4-[3-(trifluormethyl)phenoxy]-1-buten-1-yl}cyclopentyl]-5-heptensäure [German] [ACD/IUPAC Name]
(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-{(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl}cyclopentyl]-5-heptenoic acid [ACD/IUPAC Name]
(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-{(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl}cyclopentyl]hept-5-enoic acid
255-029-3 [EINECS]
40666-16-8 [RN]
5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]cyclopentyl]-, (5Z)- [ACD/Index Name]
Acide (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-{(1E,3R)-3-hydroxy-4-[3-(trifluorométhyl)phénoxy]-1-butén-1-yl}cyclopentyl]-5-hepténoïque [French] [ACD/IUPAC Name]
Equimate [Trade name]
Fluprostenol [INN]
More...

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

358S7VUE5N [DBID]
3794 [DBID]
ICI 81008 [DBID]
MEH3MCE8X1 [DBID]
UNII:358S7VUE5N [DBID]
CCRIS 4693 [DBID]
UNII:MEH3MCE8X1 [DBID]
UNII-358S7VUE5N [DBID]
UNII-MEH3MCE8X1 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      An organofluorine compound that is racemic prostaglandin F<smallsub>2<stereo>alpha</stereo></smallsub> in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic an alogue of prostaglandin F<smallsub>2<stereo>alpha</stereo></smallsub>, ophthalmic solutions of its isopropyl ester prodrug, travoprost, are used as a topical medication for controlling the progression of open-angle glaucoma and ocular hypertension, by reducing intraocular pressure. The isopropyl ester group of travoprost is hydrolysed to the biologically active free acid by esterases in the cornea . ChEBI CHEBI:60782
      An organofluorine compound that is racemic prostaglandin F2alpha in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic an; alogue of prostaglandin F2alpha, oph thalmic solutions of its isopropyl ester prodrug, travoprost, are used as a topical medication for controlling the progression; of open-angle glaucoma and ocular hypertension, by reducing intraocular pressure. The isopropyl ester group of travoprost is hydrolysed to the biologically active free acid by esterases in the cornea. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:60782
      An organofluorine compound that is racemic prostaglandin F2alpha in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic analogue of prostaglandin F2alpha, ophth almic solutions of its isopropyl ester prodrug, travoprost, are used as a topical medication for controlling the progression of open-angle glaucoma and ocular hypertension, by reducing intraocular pre ssure. The isopropyl ester group of travoprost is hydrolysed to the biologically active free acid by esterases in the cornea. ChEBI CHEBI:60782

    • Bio Activity:

      7-TM Receptors Tocris Bioscience 4542
      High affinity FP prostaglandin receptor agonist Tocris Bioscience 4542
      Prostaglandin F2? (FP) receptor agonist (Ki = 49.9 nM; EC50 = 2.4 nM). Stimulates intracellular calcium mobilization in cloned human ocular FP receptors, rat A7r5 cells and mouse 3T3 cells (EC50 value s are 17.5, 19.1 and 37.3 nM respectively). Analog of prostaglandin F2?. Isopropyl ester travaprost (Cat. No. 4218) also available. Tocris Bioscience 4542
      Prostaglandin F2? (FP) receptor agonist (Ki = 49.9 nM; EC50 = 2.4 nM). Stimulates intracellular calcium mobilization in cloned human ocular FP receptors, rat A7r5 cells and mouse 3T3 cells (EC50 values are 17.5, 19.1 and 37.3 nM respectively). Analog of prostaglandin F2?. Isopropyl ester travaprost (Cat. No. 4218) also available. Tocris Bioscience 4542
      Prostaglandin F2alpha (FP) receptor agonist (Ki = 49.9 nM; EC50 = 2.4 nM). Stimulates intracellular calcium mobilization in cloned human ocular FP receptors, rat A7r5 cells and mouse 3T3 cells (EC50 values are 17.5, 19.1 and 37.3 nM respectively). Analog of prostaglandin F2alpha. Isopropyl ester travaprost (Cat. No. 4218) also available. Tocris Bioscience 4542
      Prostanoid Receptors Tocris Bioscience 4542

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point: 608.0±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 95.0±3.0 kJ/mol
Flash Point: 321.5±31.5 °C
Index of Refraction: 1.575
Molar Refractivity: 113.5±0.3 cm3
#H bond acceptors: 6
#H bond donors: 4
#Freely Rotating Bonds: 12
#Rule of 5 Violations: 0
ACD/LogP: 2.55
ACD/LogD (pH 5.5): 1.92
ACD/BCF (pH 5.5): 10.78
ACD/KOC (pH 5.5): 112.14
ACD/LogD (pH 7.4): 0.12
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.79
Polar Surface Area: 107 Å2
Polarizability: 45.0±0.5 10-24cm3
Surface Tension: 47.6±3.0 dyne/cm
Molar Volume: 343.2±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) =  4.27

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  571.73  (Adapted Stein & Brown method)
    Melting Pt (deg C):  246.11  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.14E-016  (Modified Grain method)
    Subcooled liquid VP: 7.87E-014 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):  0.7398
       log Kow used: 4.27 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  10.643 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 :   1.81E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.560E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.27  (KowWin est)
  Log Kaw used:  -12.131  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.401
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6896
   Biowin2 (Non-Linear Model)     :   0.0509
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4594  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7629  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5836
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.9252
 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):  1.05E-011 Pa (7.87E-014 mm Hg)
  Log Koa (Koawin est  ): 16.401
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.86E+005 
       Octanol/air (Koa) model:  6.18E+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 = 155.1681 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 170.3681 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.827 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.753 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    :  1606
      Log Koc:  3.206 

 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: 4.27 (estimated)

 Volatilization from Water:
    Henry LC:  1.81E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.926E+010  hours   (2.886E+009 days)
    Half-Life from Model Lake : 7.556E+011  hours   (3.148E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              43.65  percent
    Total biodegradation:        0.43  percent
    Total sludge adsorption:    43.22  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       0.0257          0.645        1000       
   Water     16              900          1000       
   Soil      76.9            1.8e+003     1000       
   Sediment  7.08            8.1e+003     0          
     Persistence Time: 1.16e+003 hr

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