ChemSpider 2D Image | Lovastatin | C24H36O5

Lovastatin

  • Molecular FormulaC24H36O5
  • Average mass404.540 Da
  • Monoisotopic mass404.256287 Da
  • ChemSpider ID48085
  • defined stereocentres - 8 of 8 defined stereocentres


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(+)-Mevinolin
(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 (S)-2-Methylbutyrate
(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 (2S)-2-methylbutanoate [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-(2S)-2-methylbutanoat [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 (2S)-2-methylbutanoate
(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-(2S)-2-methylbutanoat
(2S)-2-Méthylbutanoate 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]
(2S)-2-méthylbutanoate 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]
(2S)-2-Methylbutanoic 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
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

L 154803 [DBID]
AIDS059059 [DBID]
AIDS-059059 [DBID]
BRN 3631989 [DBID]
CHEBI:6544 [DBID]
D00359 [DBID]
DivK1c_001032 [DBID]
HSDB 6534 [DBID]
KBio1_001032 [DBID]
KBio3_002848 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      WHITE POWDER NIH Clinical Collection [SMR000673570]
    • Safety:

      22-36/37/38 Alfa Aesar H52792
      26-36/37 Alfa Aesar H52792
      C10AA02 Wikidata Q417740
      CAUTION: May irritate eyes, skin, and respiratory tract Alfa Aesar H52792
      IRRITANT Matrix Scientific 058472
    • Target Organs:

      HDAC inhibitor;HMG-CoA reductase inhibitor;Integrin TargetMol T1207
    • Chemical Class:

      A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as <ital>A spergillus terreus</ital> and <ital>Pleurotus ostreatus</ital> (oyster mushroom). ChEBI CHEBI:40303
    • Drug Status:

      approved BIONET-Key Organics KS-1082
    • Compound Source:

      Aspergillus spp; mevinolin Microsource [01503977]
      Metab. of Aspergillus terreus and Monascus ruber Zerenex Molecular [ZBioX-0714]
      synthetic Microsource [01503977]
    • Bio Activity:

      Antihyperlipidaemic agent Zerenex Molecular [ZBioX-0714]
      Chromatin/Epigenetic; Metabolism TargetMol T1207
      Enzymes Tocris Bioscience 1530
      HDAC2;HMG-CoA reductase; Integrin TargetMol T1207
      HMG-CoA Reductase Tocris Bioscience 1530
      HMG-CoA Reductase (HMGCR) MedChem Express HY-N0504
      Lovastatin is an inhibitor of HMG-CoA reductase with IC50 of 3.4 nM, used for lowering cholesterol (hypolipidemic agent). MedChem Express http://www.medchemexpress.com/Calycosin-7-O-_beta_-D-glucoside.html, HY-N0504
      Metabolism/Protease MedChem Express HY-N0504
      Metabolism/Protease; MedChem Express HY-N0504
      Potent HMG-CoA reductase inhibitor Tocris Bioscience 1530
      Potent, competitive inhibitor of HMG-CoA reductase (Ki = 0.6 nM) therefore decreases cholesterol biosynthesis, in vitro and in vivo. Decreases CDK2, 4, 6 and cyclin E levels and induces G1 arrest and apoptosis in tumor cell lines in vitro. Inactive lactam prodrug of lovastatin hydroxy acid, naturally bioactivated in vivo following oral administration. Tocris Bioscience 1530
      Potent, competitive inhibitor of HMG-CoA reductase (Ki = 0.6 nM) therefore decreases cholesterol biosynthesis, in vitro and in vivo. Decreases CDK2, 4, 6 and cyclin E levels and induces G1 arrest and apoptosis in tumor cell lines in vitro. Inactive lactam prodrug of lovastatin hydroxy acid, naturally bioactivated in vivo following oral administration. Tocris Bioscience 1530
      Reductases Tocris Bioscience 1530

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

Density: 1.1±0.1 g/cm3
Boiling Point: 559.2±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.4 mmHg at 25°C
Enthalpy of Vaporization: 96.7±6.0 kJ/mol
Flash Point: 185.3±23.6 °C
Index of Refraction: 1.532
Molar Refractivity: 111.7±0.4 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 4.07
ACD/LogD (pH 5.5): 4.14
ACD/BCF (pH 5.5): 828.59
ACD/KOC (pH 5.5): 4271.17
ACD/LogD (pH 7.4): 4.14
ACD/BCF (pH 7.4): 828.59
ACD/KOC (pH 7.4): 4271.17
Polar Surface Area: 73 Å2
Polarizability: 44.3±0.5 10-24cm3
Surface Tension: 43.5±5.0 dyne/cm
Molar Volume: 360.6±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) =  4.74
    Log Kow (Exper. database match) =  4.26
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  510.59  (Adapted Stein & Brown method)
    Melting Pt (deg C):  197.75  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.34E-012  (Modified Grain method)
    Subcooled liquid VP: 8.86E-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):  2.137
       log Kow used: 4.26 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.10807 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.12E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.338E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.26  (exp database)
  Log Kaw used:  -8.062  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.322
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0620
   Biowin2 (Non-Linear Model)     :   0.9986
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7456  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.8514  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6213
   Biowin6 (MITI Non-Linear Model):   0.1090
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6019
 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):  1.18E-008 Pa (8.86E-011 mm Hg)
  Log Koa (Koawin est  ): 12.322
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  254 
       Octanol/air (Koa) model:  0.515 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.976 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 229.6882 E-12 cm3/molecule-sec
      Half-Life =     0.047 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.559 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    :  6491
      Log Koc:  3.812 

 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 = 2.580 (BCF = 380.4)
       log Kow used: 4.26 (expkow database)

 Volatilization from Water:
    Henry LC:  2.12E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.555E+006  hours   (2.314E+005 days)
    Half-Life from Model Lake :  6.06E+007  hours   (2.525E+006 days)

 Removal In Wastewater Treatment:
    Total removal:              43.12  percent
    Total biodegradation:        0.42  percent
    Total sludge adsorption:    42.69  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       0.00924         0.221        1000       
   Water     16.3            900          1000       
   Soil      76.7            1.8e+003     1000       
   Sediment  7.03            8.1e+003     0          
     Persistence Time: 1.13e+003 hr




                    

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