ChemSpider 2D Image | Balapiravir | C21H30N6O8

Balapiravir

  • Molecular FormulaC21H30N6O8
  • Average mass494.498 Da
  • Monoisotopic mass494.212524 Da
  • ChemSpider ID9866453

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

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

(2R,3S,4R,5R)-5-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-2-azido-2-[(isobutyryloxy)methyl]tetrahydrofuran-3,4-diyl bis(2-methylpropanoate) [ACD/IUPAC Name]
(2R,3S,4R,5R)-5-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-2-azido-2-[(isobutyryloxy)methyl]tetrahydrofuran-3,4-diyl-bis(2-methylpropanoat) [German] [ACD/IUPAC Name]
[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-2-azido-3,4-bis[(2-methylpropanoyl)oxy]oxolan-2-yl]methyl 2-methylpropanoate
690270-29-2 [RN]
balapiravir [French] [INN]
balapiravir [Spanish] [INN]
Balapiravir [INN] [USAN] [Wiki]
balapiravirum [Latin] [INN]
Bis(2-méthylpropanoate) de (2R,3S,4R,5R)-5-(4-amino-2-oxo-1(2H)-pyrimidinyl)-2-azido-2-[(isobutyryloxy)méthyl]tétrahydrofurane-3,4-diyle [French] [ACD/IUPAC Name]
VOT0LP7I9K
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

8977 [DBID]
RO4588161 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Bio Activity:

      Anti-infection MedChem Express HY-10443
      Anti-infection; MedChem Express HY-10443
      Balapiravir (R1626, Ro 4588161) is the prodrug of a nucleoside analogue inhibitor of the hepatitis C virus (HCV) RNA-dependent RNA polymerase (R1479, RG1479). MedChem Express
      Balapiravir (R1626, Ro 4588161) is the prodrug of a nucleoside analogue inhibitor of the hepatitis C virus (HCV) RNA-dependent RNA polymerase (R1479, RG1479).; IC50 Value: ; Target: HCV; Balapiravir(R-1626; R 1626; Ro 4588161) is useful for Anti HCV. MedChem Express HY-10443
      Balapiravir (R1626, Ro 4588161) is the prodrug of a nucleoside analogue inhibitor of the hepatitis C virus (HCV) RNA-dependent RNA polymerase (R1479, RG1479).;IC50 Value: ;Target: HCVBalapiravir(R-1626; R 1626; Ro 4588161) is useful for Anti HCV. Balapiravir (R1626) is the tri-isobutyrate ester prodrug of R1479 under clinical development to improve exposure of R1479 upon oral administration. Balapiravir was discontinued for safety reasons in 28-36% of patients (most often for lymphopenia) and the percentage of patients with serious adverse events (especially hematological, infection, ocular events) was dose related. Serious hematological adverse events (particularly neutropenia, lymphopenia) were more common in balapiravir recipients. Two deaths in the balapiravir/peginterferon alfa-2a/ribavirin combination groups were considered possibly related to study medication. MedChem Express HY-10443
      HCV MedChem Express HY-10443

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

Density:
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction:
Molar Refractivity:
#H bond acceptors: 14
#H bond donors: 2
#Freely Rotating Bonds: 12
#Rule of 5 Violations: 1
ACD/LogP: 3.69
ACD/LogD (pH 5.5): 2.13
ACD/BCF (pH 5.5): 24.25
ACD/KOC (pH 5.5): 335.62
ACD/LogD (pH 7.4): 2.16
ACD/BCF (pH 7.4): 25.62
ACD/KOC (pH 7.4): 354.61
Polar Surface Area: 159 Å2
Polarizability:
Surface Tension:
Molar Volume:

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™ 

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -3.89

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  714.61  (Adapted Stein & Brown method)
    Melting Pt (deg C):  312.85  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.96E-017  (Modified Grain method)
    Subcooled liquid VP: 6.77E-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):  2.922e+004
       log Kow used: -3.89 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  7944.4 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.96E-027  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.836E-022 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -3.89  (KowWin est)
  Log Kaw used:  -24.693  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.803
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5029
   Biowin2 (Non-Linear Model)     :   0.9551
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3040  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6565  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2786
   Biowin6 (MITI Non-Linear Model):   0.0184
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6552
 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):  9.03E-012 Pa (6.77E-014 mm Hg)
  Log Koa (Koawin est  ): 20.803
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.32E+005 
       Octanol/air (Koa) model:  1.56E+008 
   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 = 113.6304 E-12 cm3/molecule-sec
      Half-Life =     0.094 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.130 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.175000 E-17 cm3/molecule-sec
      Half-Life =     6.549 Days (at 7E11 mol/cm3)
   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    :  982.9
      Log Koc:  2.992 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  4.833E-002  L/mol-sec
  Kb Half-Life at pH 8:     165.992  days   
  Kb Half-Life at pH 7:       4.545  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -3.89 (estimated)

 Volatilization from Water:
    Henry LC:  4.96E-027 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.628E+023  hours   (1.095E+022 days)
    Half-Life from Model Lake : 2.866E+024  hours   (1.194E+023 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       2.25e-012       2.23         1000       
   Water     46.5            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0892          8.1e+003     0          
     Persistence Time: 973 hr

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