ChemSpider 2D Image | Compactin | C23H34O5

Compactin

  • Molecular FormulaC23H34O5
  • Average mass390.513 Da
  • Monoisotopic mass390.240631 Da
  • ChemSpider ID58262
  • defined stereocentres - 7 of 7 defined stereocentres


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

(+)-Compactin
(1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl (2S)-2-methylbutanoate [ACD/IUPAC Name]
(1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-1-naphthalinyl-(2S)-2-methylbutanoat [German] [ACD/IUPAC Name]
(1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
(2S)-2-Méthylbutanoate de (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotétrahydro-2H-pyran-2-yl]éthyl}-7-méthyl-1,2,3,7,8,8a-hexahydro-1-naphtalényle [French] [ACD/IUPAC Name]
[1S-[1a(R*),7b,8b(2S*,4S*),8ab]]-2-Methylbutanoic acid 1,2,3,7,8,8a-hexahydro-7-methyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl ester
1UQM1K0W9X
2b-Methyl-8a-(2-methyl-1-oxobutoxy)mevinic acid lactone
4943
7-[1,2,6,7,8,8a-Hexahydro-2-methyl-8-(methylbutyryloxy)naphthyl]-3-hydroxyheptan-5-olide
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C13963 [DBID]
CCRIS 4505 [DBID]
CS 500 [DBID]
CS-500 [DBID]
EU-0100754 [DBID]
L-637312 [DBID]
M2537_SIGMA [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      HMG-CoA Reductase inhibitor;CES inhibitor TargetMol T0683
    • Chemical Class:

      A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group and in which the lactone moiety has been hydrolysed to the corresponding <locant>delta</locant>-hydroxy-carboxylic acid . A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from <ital>Penicillium citrinum</ital> and from <ital>Penicillium brevicompactum</ital>, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals. ChEBI CHEBI:34848
    • Drug Status:

      experimental BIONET-Key Organics KS-1085
    • Bio Activity:

      Enzymes Tocris Bioscience 1526
      HMG-CoA Reductase Tocris Bioscience 1526
      HMG-CoA Reductase (HMGCR) MedChem Express HY-17408
      HMG-CoA Reductase ;CES 1 TargetMol T0683
      HMG-CoA reductase inhibitor Tocris Bioscience 1526
      Inhibitor of HMG-CoA reductase; decreases cholesterol biosynthesis, in vitro and in vivo. Induces apoptosis, arrests cancer cells in G1 phase and downregulates cdk 2, 4, and 6, cyclin D1 and E1, p21 a nd p27. Inactive lactam prodrug of mevastatin hydroxy acid, naturally bioactivated in vivo following oral administration. Tocris Bioscience 1526
      Inhibitor of HMG-CoA reductase; decreases cholesterol biosynthesis, in vitro and in vivo. Induces apoptosis, arrests cancer cells in G1 phase and downregulates cdk 2, 4, and 6, cyclin D1 and E1, p21 and p27. Inactive lactam prodrug of mevastatin hydroxy acid, naturally bioactivated in vivo following oral administration. Tocris Bioscience 1526
      Metabolism TargetMol T0683
      Metabolism/Protease MedChem Express HY-17408
      Metabolism/Protease; MedChem Express HY-17408
      Mevastatin (Compactin; ML236B) inhibits HMGCR (HMG-CoA reductase) (Ki for acid form is 1 nM) which in turn inhibits isoprenoid biosynthesis and therefore blocks protein isoprenylation and reduces plas ma cholesterol levels in humans. MedChem Express http://www.medchemexpress.com/strontium-ranelate.html
      Mevastatin (Compactin; ML236B) inhibits HMGCR (HMG-CoA reductase) (Ki for acid form is 1 nM) which in turn inhibits isoprenoid biosynthesis and therefore blocks protein isoprenylation and reduces plasma cholesterol levels in humans. MedChem Express HY-17408
      Reductases Tocris Bioscience 1526

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

Density: 1.1±0.1 g/cm3
Boiling Point: 555.0±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.4 mmHg at 25°C
Enthalpy of Vaporization: 96.1±6.0 kJ/mol
Flash Point: 186.5±23.6 °C
Index of Refraction: 1.535
Molar Refractivity: 107.1±0.4 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 3.57
ACD/LogD (pH 5.5): 3.87
ACD/BCF (pH 5.5): 511.04
ACD/KOC (pH 5.5): 3022.15
ACD/LogD (pH 7.4): 3.87
ACD/BCF (pH 7.4): 511.04
ACD/KOC (pH 7.4): 3022.15
Polar Surface Area: 73 Å2
Polarizability: 42.5±0.5 10-24cm3
Surface Tension: 44.5±5.0 dyne/cm
Molar Volume: 343.9±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) =  4.32
    Log Kow (Exper. database match) =  3.95
       Exper. Ref:  Sangster (1994)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  502.35  (Adapted Stein & Brown method)
    Melting Pt (deg C):  201.05  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.04E-012  (Modified Grain method)
    MP  (exp database):  152 deg C
    Subcooled liquid VP: 1.58E-010 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):  4.801
       log Kow used: 3.95 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.34461 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.60E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.605E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.95  (exp database)
  Log Kaw used:  -8.184  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.134
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0687
   Biowin2 (Non-Linear Model)     :   0.9988
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7766  (weeks       )
   Biowin4 (Primary Survey Model) :   3.8717  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6699
   Biowin6 (MITI Non-Linear Model):   0.2059
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5220
 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):  2.11E-008 Pa (1.58E-010 mm Hg)
  Log Koa (Koawin est  ): 12.134
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  142 
       Octanol/air (Koa) model:  0.334 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.964 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 228.2835 E-12 cm3/molecule-sec
      Half-Life =     0.047 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.562 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    :  4008
      Log Koc:  3.603 

 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 = 2.342 (BCF = 219.5)
       log Kow used: 3.95 (expkow database)

 Volatilization from Water:
    Henry LC:  1.6E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.231E+006  hours   (3.013E+005 days)
    Half-Life from Model Lake : 7.889E+007  hours   (3.287E+006 days)

 Removal In Wastewater Treatment:
    Total removal:              27.83  percent
    Total biodegradation:        0.30  percent
    Total sludge adsorption:    27.53  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       0.022           0.221        1000       
   Water     23.9            360          1000       
   Soil      73.4            720          1000       
   Sediment  2.73            3.24e+003    0          
     Persistence Time: 475 hr




                    

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