ChemSpider 2D Image | Oseltamivir | C16H28N2O4

Oseltamivir

  • Molecular FormulaC16H28N2O4
  • Average mass312.405 Da
  • Monoisotopic mass312.204895 Da
  • ChemSpider ID58540
  • defined stereocentres - 3 of 3 defined stereocentres


More details:



Featured data source



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

(1E)-N-[(1R,2R,6S)-6-Amino-4-(ethoxycarbonyl)-2-(3-pentanyloxy)-3-cyclohexen-1-yl]ethanimidic acid [ACD/IUPAC Name]
(1E)-N-[(1R,2R,6S)-6-Amino-4-(ethoxycarbonyl)-2-(3-pentanyloxy)-3-cyclohexen-1-yl]ethanimidsäure [German] [ACD/IUPAC Name]
(3R-(3a,4b,5a))-4-(Acetylamino)-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic Acid Ethyl Ester
(3R,4R,5S)-4-Acétamido-5-amino-3-(3-pentanyloxy)-1-cyclohexène-1-carboxylate d'éthyle [French] [ACD/IUPAC Name]
196618-13-0 [RN]
1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)- [ACD/Index Name]
1-Cyclohexene-1-carboxylic acid, 5-amino-3-(1-ethylpropoxy)-4-[[(1E)-1-hydroxyethylidene]amino]-, ethyl ester, (3R,4R,5S)- [ACD/Index Name]
204255-11-8 [RN]
20O93L6F9H
7793
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS070972 [DBID]
AIDS-070972 [DBID]
C08092 [DBID]
GS 4104 [DBID]
GS-4104 [DBID]
  • Miscellaneous
    • Chemical Class:

      A cyclohexenecarboxylate ester that is the ethyl ester of oseltamivir acid. An antiviral prodrug (it is hydrolysed to the active free carboxylic acid in the liver), it is used to slow the spread of in fluenza. ChEBI CHEBI:7798

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

Density: 1.1±0.1 g/cm3
Boiling Point: 473.3±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 73.6±3.0 kJ/mol
Flash Point: 240.0±28.7 °C
Index of Refraction: 1.502
Molar Refractivity: 84.7±0.4 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 1.50
ACD/LogD (pH 5.5): -1.07
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): 0.63
ACD/BCF (pH 7.4): 1.14
ACD/KOC (pH 7.4): 22.46
Polar Surface Area: 91 Å2
Polarizability: 33.6±0.5 10-24cm3
Surface Tension: 41.1±5.0 dyne/cm
Molar Volume: 286.8±5.0 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) =  0.95

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  445.20  (Adapted Stein & Brown method)
    Melting Pt (deg C):  187.00  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.31E-008  (Modified Grain method)
    Subcooled liquid VP: 6.46E-007 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):  1592
       log Kow used: 0.95 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2.4139e+005 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylates
       Aliphatic Amines
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.92E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.383E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.95  (KowWin est)
  Log Kaw used:  -13.923  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.873
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7896
   Biowin2 (Non-Linear Model)     :   0.9536
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6105  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.8649  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4503
   Biowin6 (MITI Non-Linear Model):   0.0824
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1213
 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):  8.61E-005 Pa (6.46E-007 mm Hg)
  Log Koa (Koawin est  ): 14.873
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0348 
       Octanol/air (Koa) model:  183 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.557 
       Mackay model           :  0.736 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 134.2485 E-12 cm3/molecule-sec
      Half-Life =     0.080 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.956 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.393750 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.720 Hrs
   Fraction sorbed to airborne particulates (phi): 0.647 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  340.3
      Log Koc:  2.532 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.954E-003  L/mol-sec
  Kb Half-Life at pH 8:      11.238  years  
  Kb Half-Life at pH 7:     112.381  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 0.95 (estimated)

 Volatilization from Water:
    Henry LC:  2.92E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.544E+012  hours   (1.477E+011 days)
    Half-Life from Model Lake : 3.866E+013  hours   (1.611E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               1.88  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.79  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       1.03e-008       1.26         1000       
   Water     41.2            900          1000       
   Soil      58.7            1.8e+003     1000       
   Sediment  0.0861          8.1e+003     0          
     Persistence Time: 1.05e+003 hr




                    

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