ChemSpider 2D Image | rosuvastatin | C22H28FN3O6S

rosuvastatin

  • Molecular FormulaC22H28FN3O6S
  • Average mass481.538 Da
  • Monoisotopic mass481.168274 Da
  • ChemSpider ID393589

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 2 of 2 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(3R,5S)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-propan-2-yl-5-pyrimidinyl]-3,5-dihydroxy-6-heptenoic acid
(3R,5S,6E)-7-{4-(4-Fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl}-3,5-dihydroxy-6-heptenoic acid [ACD/IUPAC Name]
(3R,5S,6E)-7-{4-(4-Fluorphenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl}-3,5-dihydroxy-6-heptensäure [German] [ACD/IUPAC Name]
147098-20-2 [RN]
413KH5ZJ73
6-Heptenoic acid, 7-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3,5-dihydroxy-, (3R,5S,6E)- [ACD/Index Name]
Acide (3R,5S,6E)-7-{4-(4-fluorophényl)-6-isopropyl-2-[méthyl(méthylsulfonyl)amino]-5-pyrimidinyl}-3,5-dihydroxy-6-hepténoïque [French] [ACD/IUPAC Name]
rosuvastatin [BAN] [INN] [JAN] [Wiki]
rosuvastatina [Spanish] [INN]
rosuvastatine [French] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

8021 [DBID]
KBio2_002543 [DBID]
KBio2_005111 [DBID]
KBio2_007679 [DBID]
KBio3_002932 [DBID]
KBioGR_000990 [DBID]
KBioSS_002552 [DBID]
SPBio_001140 [DBID]
Spectrum_001986 [DBID]
Spectrum2_001090 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Organofluoride; Amide; Drug; Anticholesteremic Agent; Hydroxymethylglutaryl-CoA Reductase Inhibitor; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D2680

    • Safety:

      C10AA07 Wikidata Q415159

    • Chemical Class:

      A dihydroxy monocarboxylic acid that is (6<stereo>E</stereo>)-7-{4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl} hept-6-enoic acid carrying two hydroxy substituents a t positions 3 and 5 (the 3<stereo>R</stereo>,5<stereo>S</stereo>-diastereomer). ChEBI CHEBI:38545
      A dihydroxy monocarboxylic acid that is (6E)-7-{4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl} hept-6-enoic acid carrying two hydroxy substituents at positions 3 and 5 (the 3R,5S-diastereomer). ChEBI CHEBI:38545

    • Bio Activity:

      HMG-CoA Reductase (HMGCR) MedChem Express HY-17504A
      Metabolism/Protease MedChem Express HY-17504A
      Metabolism/Protease; MedChem Express HY-17504A
      Rosuvastatin is a competitive inhibitor of HMG-CoA reductase with IC50 of 11 nM. MedChem Express http://www.medchemexpress.com/parecoxib-sodium.html, HY-17504A

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

Density: 1.4±0.1 g/cm3
Boiling Point: 745.6±70.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.6 mmHg at 25°C
Enthalpy of Vaporization: 114.1±3.0 kJ/mol
Flash Point: 404.7±35.7 °C
Index of Refraction: 1.598
Molar Refractivity: 120.0±0.4 cm3
#H bond acceptors: 9
#H bond donors: 3
#Freely Rotating Bonds: 10
#Rule of 5 Violations: 0
ACD/LogP: 0.42
ACD/LogD (pH 5.5): 0.00
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 5.63
ACD/LogD (pH 7.4): -1.77
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 149 Å2
Polarizability: 47.6±0.5 10-24cm3
Surface Tension: 62.3±3.0 dyne/cm
Molar Volume: 351.9±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) =  2.48

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  658.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  286.63  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.27E-019  (Modified Grain method)
    Subcooled liquid VP: 4.19E-016 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):  17.96
       log Kow used: 2.48 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  27568 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.50E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.859E-020 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.48  (KowWin est)
  Log Kaw used:  -14.212  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.692
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1531
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3378  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7424  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1650
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0802
 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):  5.59E-014 Pa (4.19E-016 mm Hg)
  Log Koa (Koawin est  ): 16.692
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.37E+007 
       Octanol/air (Koa) model:  1.21E+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 =  88.6254 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =  96.2254 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.448 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.334 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     6.825000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    13.650000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     4.030 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     2.015 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   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    :  15.74
      Log Koc:  1.197 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 2.48 (estimated)

 Volatilization from Water:
    Henry LC:  1.5E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.565E+012  hours   (3.569E+011 days)
    Half-Life from Model Lake : 9.344E+013  hours   (3.893E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               3.04  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.94  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       0.0736          1.69         1000       
   Water     22.4            900          1000       
   Soil      77.4            1.8e+003     1000       
   Sediment  0.177           8.1e+003     0          
     Persistence Time: 996 hr

Click to predict properties on the Chemicalize site


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