ChemSpider 2D Image | Ciglitazone | C18H23NO3S

Ciglitazone

  • Molecular FormulaC18H23NO3S
  • Average mass333.445 Da
  • Monoisotopic mass333.139862 Da
  • ChemSpider ID2648

More details:






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

2,4-Thiazolidinedione, 5-[[4-[(1-methylcyclohexyl)methoxy]phenyl]methyl]- [ACD/Index Name]
5-[4-(1-methylcyclohexylmethoxy) benzyl]-thiazolidine-2,4-dione
5-{4-[(1-Methylcyclohexyl)methoxy]benzyl}-1,3-thiazolidin-2,4-dion [German] [ACD/IUPAC Name]
5-{4-[(1-Methylcyclohexyl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione [ACD/IUPAC Name]
5-{4-[(1-Méthylcyclohexyl)méthoxy]benzyl}-1,3-thiazolidine-2,4-dione [French] [ACD/IUPAC Name]
5364
74772-77-3 [RN]
ciglitazona
Ciglitazone, (R)-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:64227 [DBID]
8D14653K4S [DBID]
ADD 3878 [DBID]
ADD-3878 [DBID]
Bio1_000144 [DBID]
Bio1_000633 [DBID]
Bio1_001122 [DBID]
Bio2_000295 [DBID]
Bio2_000775 [DBID]
C3974_SIGMA [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      An aromatic ether that consists of 1,3-thiazolidine-2,4-dione with position 5 substituted by a 4-[(1-methylcyclohexyl)methoxy]benzyl group. A selective PPAR<greek>gamma</greek> agonist. ChEBI CHEBI:64227
    • Bio Activity:

      Nuclear Receptors Tocris Bioscience 1307
      PPAR Receptors Tocris Bioscience 1307
      PPARgamma Receptors Tocris Bioscience 1307
      PPARs Tocris Bioscience 1307
      Selective agonist at PPAR? (peroxisome proliferator-activated receptor ?). Activates PPAR? with an EC50 value of 3 ?M in vitro, and is at least 33-fold selective over PPAR? and ?. Antihyperglycemic in vivo. Tocris Bioscience 1307
      Selective agonist at PPAR? (peroxisome proliferator-activated receptor ?). Activates PPAR? with an EC50 value of 3 ?M in vitro, and is at least 33-fold selective over PPAR? and ?. Antihyperglycemic in vivo. Tocris Bioscience 1307
      Selective agonist at PPARgamma (peroxisome proliferator-activated receptor gamma). Activates PPARgamma with an EC50 value of 3 muM in vitro, and is at least 33-fold selective over PPARalpha and delta. Antihyperglycemic in vivo. Tocris Bioscience 1307
      Selective PPAR? agonist Tocris Bioscience 1307
      Selective PPARgamma agonist Tocris Bioscience 1307

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

Density: 1.2±0.1 g/cm3
Boiling Point: 504.5±23.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 77.4±3.0 kJ/mol
Flash Point: 258.9±22.6 °C
Index of Refraction: 1.568
Molar Refractivity: 91.7±0.3 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 4.69
ACD/LogD (pH 5.5): 3.69
ACD/BCF (pH 5.5): 366.63
ACD/KOC (pH 5.5): 2296.86
ACD/LogD (pH 7.4): 2.71
ACD/BCF (pH 7.4): 38.37
ACD/KOC (pH 7.4): 240.36
Polar Surface Area: 81 Å2
Polarizability: 36.4±0.5 10-24cm3
Surface Tension: 45.7±3.0 dyne/cm
Molar Volume: 280.4±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) =  5.13

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  582.37  (Adapted Stein & Brown method)
    Melting Pt (deg C):  251.08  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.36E-013  (Modified Grain method)
    Subcooled liquid VP: 2.12E-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):  0.3265
       log Kow used: 5.13 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.93832 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.68E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.890E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.13  (KowWin est)
  Log Kaw used:  -5.960  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.090
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5914
   Biowin2 (Non-Linear Model)     :   0.3489
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1172  (months      )
   Biowin4 (Primary Survey Model) :   3.2218  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1211
   Biowin6 (MITI Non-Linear Model):   0.0287
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4378
 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):  2.83E-008 Pa (2.12E-010 mm Hg)
  Log Koa (Koawin est  ): 11.090
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  106 
       Octanol/air (Koa) model:  0.0302 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.707 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  60.6777 E-12 cm3/molecule-sec
      Half-Life =     0.176 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.115 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  1.033E+004
      Log Koc:  4.014 

 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 = 3.247 (BCF = 1766)
       log Kow used: 5.13 (estimated)

 Volatilization from Water:
    Henry LC:  2.68E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.989E+004  hours   (1662 days)
    Half-Life from Model Lake : 4.354E+005  hours   (1.814E+004 days)

 Removal In Wastewater Treatment:
    Total removal:              81.42  percent
    Total biodegradation:        0.70  percent
    Total sludge adsorption:    80.72  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       0.0647          4.23         1000       
   Water     7.53            1.44e+003    1000       
   Soil      62              2.88e+003    1000       
   Sediment  30.4            1.3e+004     0          
     Persistence Time: 2.53e+003 hr




                    

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