ChemSpider 2D Image | Tolrestat | C16H14F3NO3S

Tolrestat

  • Molecular FormulaC16H14F3NO3S
  • Average mass357.348 Da
  • Monoisotopic mass357.064636 Da
  • ChemSpider ID48194

More details:

Featured data source
The Merck Index Online

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

[(6-Methoxy-5-trifluoromethyl-naphthalene-1-carbothioyl)-methyl-amino]-acetic acid
0T93LG5NMK
82964-04-3 [RN]
Glycine, N-[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]thioxomethyl]-N-methyl- [ACD/Index Name]
N-[[6-Methoxy-5-(trifluoromethyl)-1-naphthalenyl]thioxomethyl]-N-methylglycine
N-{[6-Methoxy-5-(trifluormethyl)-1-naphthyl]carbonothioyl}-N-methylglycin [German] [ACD/IUPAC Name]
N-{[6-Methoxy-5-(trifluoromethyl)-1-naphthyl]carbonothioyl}-N-methylglycine [ACD/IUPAC Name]
N-{[6-Methoxy-5-(trifluoromethyl)-1-naphthyl]carbothioyl}-N-methylglycine
N-{[6-Méthoxy-5-(trifluorométhyl)-1-naphtyl]carbonothioyl}-N-méthylglycine [French] [ACD/IUPAC Name]
N-{[6-methoxy-5-(trifluoromethyl)naphthalen-1-yl]carbothioyl}-N-methylglycine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

5529 [DBID]
AY 27773 [DBID]
AY-27773 [DBID]
C01621 [DBID]
D02323 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      A10XA01 Wikidata Q7814620

    • Therapeutical Effect:

      Enzyme Inhibitors Sean Ekins

    • Bio Activity:

      Aldose Reductase MedChem Express HY-16500
      Metabolic Enzyme/Protease; MedChem Express HY-16500
      Others MedChem Express HY-16500
      Tolrestat(AY-27773) is a potent, orally active aldose reductase inhibitor with IC50 value of 35 nM. MedChem Express
      Tolrestat(AY-27773) is a potent, orally active aldose reductase inhibitor with IC50 value of 35 nM.; IC50 value: 35 nM [1]; Target: aldose reductase; in vitro: Tolrestat inhibited in dose-dependent fashion the AR from bovine lenses (IC50, 3.5 X 10(-8) mol/L) and the formation of sorbitol in human RBC incubated with glucose (IC50, 3 X 10(-8) mol/L). MedChem Express HY-16500
      Tolrestat(AY-27773) is a potent, orally active aldose reductase inhibitor with IC50 value of 35 nM.;IC50 value: 35 nM [1];Target: aldose reductase;In vitro: Tolrestat inhibited in dose-dependent fashion the AR from bovine lenses (IC50, 3.5 X 10(-8) mol/L) and the formation of sorbitol in human RBC incubated with glucose (IC50, 3 X 10(-8) mol/L). Upon administration with the diet to rats made galactosemic or diabetic, tolrestat decreased, in a dose-related fashion, the accumulation of galactitol or sorbitol in the sciatic nerve and lens [2].;In vivo: The effectiveness of tolrestat depended upon the experimental conditions and tended to be higher in less severe galactosemia and after suitable pretreatment, particularly in galactosemic rats, resulting in ID50 of 5 mg/kg/d in the sciatic nerve and 12-15 mg/kg/d in the lens. Tolrestat also decreased, in dose-related manner, the RBC sorbitol levels in normal and in streptozotocin diabetic rats; in the latter, at less than 2 mg/kg/d, the MedChem Express HY-16500
  • Gas Chromatography

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

Density: 1.4±0.1 g/cm3
Boiling Point: 498.1±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 80.7±3.0 kJ/mol
Flash Point: 255.0±31.5 °C
Index of Refraction: 1.602
Molar Refractivity: 87.6±0.3 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 3.41
ACD/LogD (pH 5.5): 1.26
ACD/BCF (pH 5.5): 1.39
ACD/KOC (pH 5.5): 8.90
ACD/LogD (pH 7.4): 0.05
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 82 Å2
Polarizability: 34.7±0.5 10-24cm3
Surface Tension: 49.9±3.0 dyne/cm
Molar Volume: 255.4±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) =  1.80

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  452.26  (Adapted Stein & Brown method)
    Melting Pt (deg C):  190.30  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8E-009  (Modified Grain method)
    Subcooled liquid VP: 4.32E-007 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):  1.377
       log Kow used: 1.80 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.1842 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.41E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.732E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.80  (KowWin est)
  Log Kaw used:  -9.239  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.039
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4718
   Biowin2 (Non-Linear Model)     :   0.1041
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1488  (months      )
   Biowin4 (Primary Survey Model) :   3.7259  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2955
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0227
 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):  5.76E-005 Pa (4.32E-007 mm Hg)
  Log Koa (Koawin est  ): 11.039
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0521 
       Octanol/air (Koa) model:  0.0269 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.653 
       Mackay model           :  0.806 
       Octanol/air (Koa) model:  0.682 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  28.0452 E-12 cm3/molecule-sec
      Half-Life =     0.381 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     4.577 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.73 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  654.7
      Log Koc:  2.816 

 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: 1.80 (estimated)

 Volatilization from Water:
    Henry LC:  1.41E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.849E+007  hours   (3.271E+006 days)
    Half-Life from Model Lake : 8.563E+008  hours   (3.568E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               2.10  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     2.00  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       0.000405        9.15         1000       
   Water     27.7            1.44e+003    1000       
   Soil      72.2            2.88e+003    1000       
   Sediment  0.0886          1.3e+004     0          
     Persistence Time: 1.71e+003 hr

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