ChemSpider 2D Image | (+)-Simvastatin | C25H38O5

(+)-Simvastatin

  • Molecular FormulaC25H38O5
  • Average mass418.566 Da
  • Monoisotopic mass418.271912 Da
  • ChemSpider ID49179

  • defined stereocentres - 7 of 7 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(+)-Simvastatin
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl 2,2-dimethylbutanoate [ACD/IUPAC Name]
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalinyl-2,2-dimethylbutanoat [German] [ACD/IUPAC Name]
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl-2,2-dimethylbutanoat [German]
[1S-[1a,3a,7b,8b(2S*,4S*),8ab]]-2,2-Dimethylbutanoic Acid1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl Ester
2,2-Diméthylbutanoate de (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotétrahydro-2H-pyran-2-yl]éthyl}-3,7-diméthyl-1,2,3,7,8,8a-hexahydro-1-naphtalényle [French] [ACD/IUPAC Name]
2,2-diméthylbutanoate de (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotétrahydro-2H-pyran-2-yl]éthyl}-3,7-diméthyl-1,2,3,7,8,8a-hexahydronaphtalén-1-yle [French]
2,2-Dimethylbutanoic acid (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester
2,2-Dimethylbutyric Acid 8-Ester with (4R,6R)-6-[2-[(1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-Hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl]ethyl]tetrahydro-4-hydroxy-2H-pyran-2-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

6147 [DBID]
DRG 0320 [DBID]
GMK-733 [DBID]
MK 733 [DBID]
AIDS111666 [DBID]
AIDS-111666 [DBID]
BRN 4768037 [DBID]
CCRIS 7558 [DBID]
CHEBI:9150 [DBID]
D00434 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Ether; Ester; Drug; Food Toxin; Anticholesteremic Agent; Hydroxymethylglutaryl-CoA Reductase Inhibitor; Metabolite; Fungal Toxin; Synthetic Compound; Hypolipidemic Agent Toxin, Toxin-Target Database T3D4788

    • Safety:

      C10AA01 Wikidata Q670131

    • Target Organs:

      MRP inhibitor; HMG-CoA Reductase inhibitor; Integrin TargetMol T0687

    • Chemical Class:

      A carbobicyclic compound that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovasc ular disease drug. ChEBI CHEBI:9150
      A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-loweri ng and anti-cardiovascular disease drug. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9150

    • Bio Activity:

      Enzymes Tocris Bioscience 1965
      HMG-CoA Reductase Tocris Bioscience 1965
      HMG-CoA Reductase (HMGCR) MedChem Express HY-17502
      HMG-CoA reductase inhibitor Tocris Bioscience 1965
      HMG-CoA reductase inhibitor; decreases levels of low density lipoprotein. Has multiple biological effects including bone formation stimulation, inhibition of smooth muscle cell proliferation and migra tion, and anticancer and anti-inflammatory activity. Inactive lactone prodrug of simvastatin hydroxy acid, naturally bioactivated in vivo following oral administration. Tocris Bioscience 1965
      HMG-CoA reductase inhibitor; decreases levels of low density lipoprotein. Has multiple biological effects including bone formation stimulation, inhibition of smooth muscle cell proliferation and migration, and anticancer and anti-inflammatory activity. Inactive lactone prodrug of simvastatin hydroxy acid, naturally bioactivated in vivo following oral administration. Tocris Bioscience 1965
      HMG-CoA reductase inhibitor; decreases levels of low density lipoprotein. Has multiple biological effects including bone formation stimulation, inhibition of smooth muscle cell proliferation and migration, induction of ferroptosis, and anticancer and anti-inflammatory activity. Inactive lactone prodrug of simvastatin hydroxy acid, naturally bioactivated in vivo following oral administration. Deuterated analog also available. Tocris Bioscience 1965
      Metabolism TargetMol T0687
      Metabolism/Protease MedChem Express HY-17502
      Metabolism/Protease; MedChem Express HY-17502
      MRP1; HMG-CoA Reductase ; Integrin beta-2 TargetMol T0687
      Reductases Tocris Bioscience 1965
      Simvastatin is a competitive inhibitor of HMG-CoA reductase with Ki of 0.1-0.2 nM . MedChem Express
      Simvastatin is a competitive inhibitor of HMG-CoA reductase with Ki of 0.1-0.2 nM .; Target: HMG-CoA reductase; Simvastatin inhibits cholesterol synthesis in mouse L-M cell (fibroblast), rat H4II E cell (liver), and human Hep G2 cell (liver) with IC50 of 19.3 nM, 13.3 nM and 15.6 nM, respectively [1]. MedChem Express HY-17502

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

Density: 1.1±0.1 g/cm3
Boiling Point: 564.9±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.5 mmHg at 25°C
Enthalpy of Vaporization: 97.5±6.0 kJ/mol
Flash Point: 184.8±23.6 °C
Index of Refraction: 1.530
Molar Refractivity: 116.4±0.4 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 4.41
ACD/LogD (pH 5.5): 4.60
ACD/BCF (pH 5.5): 1855.12
ACD/KOC (pH 5.5): 7604.98
ACD/LogD (pH 7.4): 4.60
ACD/BCF (pH 7.4): 1855.12
ACD/KOC (pH 7.4): 7604.98
Polar Surface Area: 73 Å2
Polarizability: 46.1±0.5 10-24cm3
Surface Tension: 43.1±5.0 dyne/cm
Molar Volume: 376.6±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) =  5.19
    Log Kow (Exper. database match) =  4.68
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  517.59  (Adapted Stein & Brown method)
    Melting Pt (deg C):  206.76  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.23E-012  (Modified Grain method)
    MP  (exp database):  135-138 deg C
    Subcooled liquid VP: 5.4E-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):  0.7653
       log Kow used: 4.68 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.047687 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.81E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.044E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.68  (exp database)
  Log Kaw used:  -7.940  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.620
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8714
   Biowin2 (Non-Linear Model)     :   0.9902
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5024  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6778  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6983
   Biowin6 (MITI Non-Linear Model):   0.1205
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3540
 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):  7.2E-009 Pa (5.4E-011 mm Hg)
  Log Koa (Koawin est  ): 12.620
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  417 
       Octanol/air (Koa) model:  1.02 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.988 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 229.1157 E-12 cm3/molecule-sec
      Half-Life =     0.047 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.560 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    :  9643
      Log Koc:  3.984 

 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 = 2.904 (BCF = 800.9)
       log Kow used: 4.68 (expkow database)

 Volatilization from Water:
    Henry LC:  2.81E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.263E+006  hours   (1.776E+005 days)
    Half-Life from Model Lake :  4.65E+007  hours   (1.938E+006 days)

 Removal In Wastewater Treatment:
    Total removal:              65.05  percent
    Total biodegradation:        0.59  percent
    Total sludge adsorption:    64.46  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       0.00839         0.221        1000       
   Water     14.2            900          1000       
   Soil      69.9            1.8e+003     1000       
   Sediment  16              8.1e+003     0          
     Persistence Time: 1.25e+003 hr

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