ChemSpider 2D Image | Bimatoprost | C25H37NO4

Bimatoprost

  • Molecular FormulaC25H37NO4
  • Average mass415.566 Da
  • Monoisotopic mass415.272247 Da
  • ChemSpider ID4470565
  • 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

(5Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl}-N-ethyl-5-heptenamid [German] [ACD/IUPAC Name]
(5Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl}-N-ethyl-5-heptenamide [ACD/IUPAC Name]
(5Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phényl-1-pentén-1-yl]cyclopentyl}-N-éthyl-5-hepténamide [French] [ACD/IUPAC Name]
(5Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide
155206-00-1 [RN]
5-Heptenamide, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-, (5Z)- [ACD/Index Name]
8035
bimatoprost [French] [INN]
bimatoprost [Spanish] [INN]
Bimatoprost [USAN] [Wiki]
More...

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

AGN 192024 [DBID]
AGN-192024 [DBID]
D02724 [DBID]
LS-181817 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      S01EE03 Wikidata Q2393348
    • Target Organs:

      PGE2 inhibitor TargetMol T2538
    • Bio Activity:

      Bimatoprost is a prostaglandin analog used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension.; Target: Prostaglandin Receptor; Bimatoprost is a prostaglandin analog/prodrug used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. MedChem Express HY-B0191
      Bimatoprost is a prostaglandin analog used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension.;Target: Prostaglandin ReceptorBimatoprost is a prostaglandin analog/prodrug used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. It reduces intraocular pressure (IOP) by increasing the outflow of aqueous fluid from the eyes. In December 2008, the indication to lengthen eyelashes was approved by the U.S. Food and Drug Administration (FDA); the cosmetic formulation of bimatoprost is sold as Latisse. In 2008-2011, at least three case series suggested that bimatoprost has the ability to reduce adipose (fat) tissue.Bimatoprost activates prostamide alpha F2 receptors found in the hair follicle to stimulate its growth rate. Research led by Professor Randall and the University of Bradford found that it may also offer a treatment for scalp hair regrowth in trials conducted on s MedChem Express HY-B0191
      GPCR/G protein MedChem Express HY-B0191
      GPCR/G protein; MedChem Express HY-B0191
      Immunology/Inflammation TargetMol T2538
      PGE2, PGF2 TargetMol T2538
      Prostaglandin Receptor MedChem Express HY-B0191

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

Density: 1.1±0.1 g/cm3
Boiling Point: 629.8±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 97.9±3.0 kJ/mol
Flash Point: 334.7±31.5 °C
Index of Refraction: 1.591
Molar Refractivity: 122.7±0.3 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 12
#Rule of 5 Violations: 0
ACD/LogP: 1.98
ACD/LogD (pH 5.5): 2.37
ACD/BCF (pH 5.5): 37.24
ACD/KOC (pH 5.5): 463.61
ACD/LogD (pH 7.4): 2.37
ACD/BCF (pH 7.4): 37.24
ACD/KOC (pH 7.4): 463.61
Polar Surface Area: 90 Å2
Polarizability: 48.6±0.5 10-24cm3
Surface Tension: 48.0±3.0 dyne/cm
Molar Volume: 362.8±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) =  3.97

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  616.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  267.01  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.27E-018  (Modified Grain method)
    Subcooled liquid VP: 2.39E-015 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):  0.9948
       log Kow used: 3.97 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  68.1 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.08E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.897E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.97  (KowWin est)
  Log Kaw used:  -12.900  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.870
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.4188
   Biowin2 (Non-Linear Model)     :   0.9960
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6537  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7783  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4117
   Biowin6 (MITI Non-Linear Model):   0.0591
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0600
 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):  3.19E-013 Pa (2.39E-015 mm Hg)
  Log Koa (Koawin est  ): 16.870
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  9.41E+006 
       Octanol/air (Koa) model:  1.82E+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 = 164.3571 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 179.5571 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.781 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.715 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    :  2.307E+004
      Log Koc:  4.363 

 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 = 1.708 (BCF = 51.04)
       log Kow used: 3.97 (estimated)

 Volatilization from Water:
    Henry LC:  3.08E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.875E+011  hours   (1.615E+010 days)
    Half-Life from Model Lake : 4.227E+012  hours   (1.761E+011 days)

 Removal In Wastewater Treatment:
    Total removal:              28.71  percent
    Total biodegradation:        0.31  percent
    Total sludge adsorption:    28.40  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       0.0263          0.631        1000       
   Water     16.9            900          1000       
   Soil      79.3            1.8e+003     1000       
   Sediment  3.72            8.1e+003     0          
     Persistence Time: 1.11e+003 hr




                    

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