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ChemSpider 2D Image | Cerivastatin | C26H34FNO5

Cerivastatin

  • Molecular FormulaC26H34FNO5
  • Average mass459.550 Da
  • Monoisotopic mass459.242096 Da
  • ChemSpider ID393588
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 2 of 2 defined stereocentres


More details:



Featured data source



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

(3R,5S)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-di(propan-2-yl)-3-pyridinyl]-3,5-dihydroxy-6-heptenoic acid
(3R,5S,6E)-7-[4-(4-Fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)-3-pyridinyl]-3,5-dihydroxy-6-heptenoic acid [ACD/IUPAC Name]
(3R,5S,6E)-7-[4-(4-Fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
(3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
(3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-di(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
(3R,5S,6E)-7-[4-(4-Fluorphenyl)-2,6-diisopropyl-5-(methoxymethyl)-3-pyridinyl]-3,5-dihydroxy-6-heptensäure [German] [ACD/IUPAC Name]
(3R,5S,6E)-7-{4-(4-fluorophenyl)-2,6-bis(1-methylethyl)-5-[(methyloxy)methyl]pyridin-3-yl}-3,5-dihydroxyhept-6-enoic acid
[S-[R*,S*-(E)]]-7-[4-(4-Fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl]-3,5-dihydroxy-6-heptenoic Acid
145599-86-6 [RN]
6-Heptenoic acid, 7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl]-3,5-dihydroxy-, (3R,5S,6E)- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AM91H2KS67 [DBID]
C07966 [DBID]
nchembio790-comp12 [DBID]
PubChem Substance ID 329831176 [DBID]
UNII:AM91H2KS67 [DBID]
UNII-AM91H2KS67 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      C10AA06 Wikidata Q423439
    • Chemical Class:

      (3<stereo>R</stereo>,5<stereo>S</stereo>)-3,5-dihydroxyhept-6-enoic acid in which the (7<stereo>E</stereo>)-hydrogen is substituted by a 4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-y l group. Formerly used (as its sodium salt) to lower cholesterol and prevent cardiovascular disease, it was withdrawn from the market worldwide in 2001 following reports of a severe form of muscle tox icity. ChEBI CHEBI:3558
    • Therapeutical Effect:

      Hydroxymethylglutaryl-CoA Reductase Inhibitors Sean Ekins

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

Density: 1.2±0.1 g/cm3
Boiling Point: 646.3±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 100.2±3.0 kJ/mol
Flash Point: 344.7±31.5 °C
Index of Refraction: 1.570
Molar Refractivity: 127.6±0.3 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 11
#Rule of 5 Violations: 0
ACD/LogP: 3.70
ACD/LogD (pH 5.5): 2.00
ACD/BCF (pH 5.5): 7.64
ACD/KOC (pH 5.5): 49.26
ACD/LogD (pH 7.4): 0.59
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.91
Polar Surface Area: 100 Å2
Polarizability: 50.6±0.5 10-24cm3
Surface Tension: 47.4±3.0 dyne/cm
Molar Volume: 388.9±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) =  4.83

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  599.43  (Adapted Stein & Brown method)
    Melting Pt (deg C):  259.04  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.03E-016  (Modified Grain method)
    Subcooled liquid VP: 3.73E-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):  0.2393
       log Kow used: 4.83 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  284.43 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 :   5.77E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.603E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.83  (KowWin est)
  Log Kaw used:  -16.627  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.457
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.2837
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0887  (months      )
   Biowin4 (Primary Survey Model) :   3.6771  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1967
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2958
 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):  4.97E-012 Pa (3.73E-014 mm Hg)
  Log Koa (Koawin est  ): 21.457
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.03E+005 
       Octanol/air (Koa) model:  7.03E+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 =  93.9732 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 101.5732 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.366 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.264 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    :  682.6
      Log Koc:  2.834 

 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: 4.83 (estimated)

 Volatilization from Water:
    Henry LC:  5.77E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.175E+015  hours   (9.064E+013 days)
    Half-Life from Model Lake : 2.373E+016  hours   (9.887E+014 days)

 Removal In Wastewater Treatment:
    Total removal:              71.60  percent
    Total biodegradation:        0.64  percent
    Total sludge adsorption:    70.96  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       0.0001          1.63         1000       
   Water     6.78            1.44e+003    1000       
   Soil      79              2.88e+003    1000       
   Sediment  14.2            1.3e+004     0          
     Persistence Time: 3.32e+003 hr




                    

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