ChemSpider 2D Image | Atovaquone | C22H19ClO3

Atovaquone

  • Molecular FormulaC22H19ClO3
  • Average mass366.837 Da
  • Monoisotopic mass366.102264 Da
  • ChemSpider ID10482034
  • defined stereocentres - 2 of 2 defined stereocentres


More details:



Featured data source



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

1,4-Naphthalenedione, 2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy- [ACD/Index Name]
2-[trans-4-(4-chlorophenyl)cyclohexyl]-3- hydroxy-1,4-naphthoquinone
2-[trans-4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone [ACD/IUPAC Name]
2-[trans-4-(4-Chlorophényl)cyclohexyl]-3-hydroxy-1,4-naphtoquinone [French] [ACD/IUPAC Name]
2-[trans-4-(4-chlorophényl)cyclohexyl]-3-hydroxynaphtalène-1,4-dione
2-[trans-4-(4-Chlorphenyl)cyclohexyl]-3-hydroxy-1,4-naphthochinon [German] [ACD/IUPAC Name]
2-[trans-4-(4-Chlorphenyl)cyclohexyl]-3-hydroxynaphthalen-1,4-dion
2-[trans-4-(p-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone
566C80
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Drug Status:

      USP, INN, BAN Microsource [01504210]
    • Compound Source:

      synthetic Microsource [01504210]
    • Bio Activity:

      Anti-infection MedChem Express HY-13832
      Anti-infection; MedChem Express HY-13832
      Antiparasitic MedChem Express HY-13832
      Antiprotozoal; Zerenex Molecular [ZBioX-0108]
      Atovaquone is a medication used to treat or prevent for pneumocystis pneumonia, toxoplasmosis, malaria, and babesia. MedChem Express
      Atovaquone is a medication used to treat or prevent for pneumocystis pneumonia, toxoplasmosis, malaria, and babesia.; Target: Antiparasitic; Atovaquone (atavaquone) is a chemical compound that belongs to the class of naphthalenes. MedChem Express HY-13832
      Atovaquone is a medication used to treat or prevent for pneumocystis pneumonia, toxoplasmosis, malaria, and babesia.;Target: AntiparasiticAtovaquone (atavaquone) is a chemical compound that belongs to the class of naphthalenes. Atovaquone is a hydroxy-1,4-naphthoquinone, an analog of ubiquinone, with antipneumocystic activity [1]. Atovaquone is an anti-protozoal mitochondrial electron transport inhibitor; Antimalarial; Antipneumocystic, and has also been used to treat toxoplasmosis. It acts by inhibiting the cytochrome bc(1) complex via interactions with the Rieske iron-sulfur protein and cytochrome b in the ubiquinol oxidation pocket [2]. Atovaquone is a unique naphthoquinone with broad-spectrum antiprotozoal activity. It is effective for the treatment and prevention of Pneumocystis carinii pneumonia (PCP), it is effective in combination with proguanil for the treatment and prevention of malaria, and it is effective in combination with azithromycin for the treatment of babesiosis MedChem Express HY-13832

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

Density: 1.4±0.1 g/cm3
Boiling Point: 535.0±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 85.4±3.0 kJ/mol
Flash Point: 277.3±30.1 °C
Index of Refraction: 1.653
Molar Refractivity: 99.5±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: 6.18
ACD/LogD (pH 5.5): 4.24
ACD/BCF (pH 5.5): 705.02
ACD/KOC (pH 5.5): 2552.54
ACD/LogD (pH 7.4): 2.49
ACD/BCF (pH 7.4): 12.60
ACD/KOC (pH 7.4): 45.63
Polar Surface Area: 54 Å2
Polarizability: 39.5±0.5 10-24cm3
Surface Tension: 60.5±3.0 dyne/cm
Molar Volume: 271.8±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) =  5.87

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  530.56  (Adapted Stein & Brown method)
    Melting Pt (deg C):  226.87  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.47E-013  (Modified Grain method)
    Subcooled liquid VP: 2.15E-011 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):  0.04742
       log Kow used: 5.87 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.0036502 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Quinone/Hydroquinone

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.74E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.496E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.87  (KowWin est)
  Log Kaw used:  -11.400  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.270
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6175
   Biowin2 (Non-Linear Model)     :   0.0315
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2220  (months      )
   Biowin4 (Primary Survey Model) :   3.1696  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1709
   Biowin6 (MITI Non-Linear Model):   0.0273
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.5026
 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):  2.87E-009 Pa (2.15E-011 mm Hg)
  Log Koa (Koawin est  ): 17.270
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.05E+003 
       Octanol/air (Koa) model:  4.57E+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 =  27.5370 E-12 cm3/molecule-sec
      Half-Life =     0.388 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     4.661 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    13.650000 E-17 cm3/molecule-sec
      Half-Life =     0.084 Days (at 7E11 mol/cm3)
      Half-Life =      2.015 Hrs
   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    :  953.5
      Log Koc:  2.979 

 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 = 2.981 (BCF = 956.5)
       log Kow used: 5.87 (estimated)

 Volatilization from Water:
    Henry LC:  9.74E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.151E+010  hours   (4.797E+008 days)
    Half-Life from Model Lake : 1.256E+011  hours   (5.233E+009 days)

 Removal In Wastewater Treatment:
    Total removal:              91.51  percent
    Total biodegradation:        0.76  percent
    Total sludge adsorption:    90.75  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       0.00901         1.66         1000       
   Water     3.06            1.44e+003    1000       
   Soil      47.1            2.88e+003    1000       
   Sediment  49.9            1.3e+004     0          
     Persistence Time: 4.28e+003 hr




                    

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