ChemSpider 2D Image | Pravastatin | C23H36O7

Pravastatin

  • Molecular FormulaC23H36O7
  • Average mass424.528 Da
  • Monoisotopic mass424.246094 Da
  • ChemSpider ID49398
  • defined stereocentres - 8 of 8 defined stereocentres


More details:






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

(3R,5R)-3,5-Dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydro-1-naphthalenyl]heptanoic acid [ACD/IUPAC Name]
(3R,5R)-3,5-Dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydro-1-naphthalinyl]heptansäure [German] [ACD/IUPAC Name]
(3R,5R)-3,5-Dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic acid
1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-β,δ,6-trihydroxy-2-methyl-8-[(2S)-2-methyl-1-oxobutoxy]-, (βR,δR,1S,2S,6S,8S,8aR)- [ACD/Index Name]
6070
81093-37-0 [RN]
Acide (3R,5R)-3,5-dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-méthyl-8-{[(2S)-2-méthylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydro-1-naphtalényl]heptanoïque [French] [ACD/IUPAC Name]
KXO2KT9N0G
Pravachol
Pravastatin [INN] [Wiki]
More...

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

CHEBI:63618 [DBID]
C01844 [DBID]
CCRIS 7557 [DBID]
EPA Pesticide Chemical Code 079011 [DBID]
nchembio790-comp15 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      C10AA03 Wikidata Q1240093
    • Chemical Class:

      A carboxylic ester resulting from the formal condensation of (<stereo>S</stereo>)-2-methylbutyric acid with the hydroxy group adjacent to the ring junction of (3<stereo>R</stereo>,5<stereo>R</stereo>) -7-[(1<stereo>S</stereo>,2<stereo>S</stereo>,6<stereo>S</stereo>,8<stereo>S</stereo>,8a<stereo>R</stereo>)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid. De rived from microbial transformation of mevastatin, pravastatin is a reversible inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA). The sodium salt is used for lowering cholesterol and preven ting cardiovascular disease. It is one of the lower potency statins, but has the advantage of fewer side effects compared with lovastatin and simvastatin. ChEBI CHEBI:63618
    • Drug Status:

      approved BIONET-Key Organics KS-5015
    • Bio Activity:

      HMG-CoA Reductase (HMGCR) MedChem Express HY-B0165
      Metabolism/Protease MedChem Express HY-B0165
      Metabolism/Protease; MedChem Express HY-B0165
      Pravastatin is an HMG-CoA reductase inhibitor against sterol synthesis with IC50 of 5.6 ?M.; Target: HMG-CoA reductase; Pravastatin (marketed as Pravachol or Selektine) is a member of the drug class of statins, used in combination with diet, exercise, and weight-loss for lowering cholesterol and preventing cardiovascular disease.; Pravastatin is primarily used for the treatment of dyslipidemia and the prevention of cardiovascular disease. MedChem Express HY-B0165

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

Density: 1.2±0.1 g/cm3
Boiling Point: 634.5±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.2 mmHg at 25°C
Enthalpy of Vaporization: 107.5±6.0 kJ/mol
Flash Point: 213.2±25.0 °C
Index of Refraction: 1.555
Molar Refractivity: 112.0±0.4 cm3
#H bond acceptors: 7
#H bond donors: 4
#Freely Rotating Bonds: 11
#Rule of 5 Violations: 0
ACD/LogP: 1.35
ACD/LogD (pH 5.5): 1.02
ACD/BCF (pH 5.5): 1.71
ACD/KOC (pH 5.5): 21.65
ACD/LogD (pH 7.4): -0.75
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 124 Å2
Polarizability: 44.4±0.5 10-24cm3
Surface Tension: 54.0±5.0 dyne/cm
Molar Volume: 349.1±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) =  3.10

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  564.52  (Adapted Stein & Brown method)
    Melting Pt (deg C):  242.74  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.04E-016  (Modified Grain method)
    Subcooled liquid VP: 1.38E-013 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):  12.06
       log Kow used: 3.10 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  590.28 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.01E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.798E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.10  (KowWin est)
  Log Kaw used:  -13.085  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.185
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2685
   Biowin2 (Non-Linear Model)     :   0.9937
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2457  (weeks       )
   Biowin4 (Primary Survey Model) :   4.2381  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6543
   Biowin6 (MITI Non-Linear Model):   0.1742
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8434
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  1.84E-011 Pa (1.38E-013 mm Hg)
  Log Koa (Koawin est  ): 16.185
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.63E+005 
       Octanol/air (Koa) model:  3.76E+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 = 242.3684 E-12 cm3/molecule-sec
      Half-Life =     0.044 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.530 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =   100.000000 E-17 cm3/molecule-sec
      Half-Life =     0.011 Days (at 7E11 mol/cm3)
      Half-Life =     16.502 Min
   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    :  107.3
      Log Koc:  2.031 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.534E-003  L/mol-sec
  Kb Half-Life at pH 8:      14.322  years  
  Kb Half-Life at pH 7:     143.216  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 3.10 (estimated)

 Volatilization from Water:
    Henry LC:  2.01E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.002E+011  hours   (2.501E+010 days)
    Half-Life from Model Lake : 6.547E+012  hours   (2.728E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               6.64  percent
    Total biodegradation:        0.13  percent
    Total sludge adsorption:     6.50  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       0.0212          0.218        1000       
   Water     24.7            360          1000       
   Soil      74.8            720          1000       
   Sediment  0.499           3.24e+003    0          
     Persistence Time: 472 hr




                    

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