ChemSpider 2D Image | tioxolone | C7H4O3S


  • Molecular FormulaC7H4O3S
  • Average mass168.170 Da
  • Monoisotopic mass167.988113 Da
  • ChemSpider ID65113

More details:

Featured data source

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

1,3-Benzoxathiol-2-one, 6-hydroxy- [ACD/Index Name]
225-653-0 [EINECS]
4991-65-5 [RN]
6-Hydroxy-1,3-benzoxathiol-2-on [German] [ACD/IUPAC Name]
6-Hydroxy-1,3-benzoxathiol-2-one [ACD/IUPAC Name]
6-Hydroxy-1,3-benzoxathiol-2-one [French] [ACD/IUPAC Name]

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

MFCD00005859 [DBID]
DivK1c_006997 [DBID]
KBio1_001941 [DBID]
KBio2_001838 [DBID]
KBio2_004406 [DBID]
KBio2_006974 [DBID]
KBio3_002029 [DBID]
KBioGR_001731 [DBID]
KBioSS_001838 [DBID]
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      Carbonic anhydrase inhibitor TargetMol T0515
    • Chemical Class:

      A 1,3-benzoxathiole having a hydroxy substituent at the 6-position. ChEBI CHEBI:568021
    • Drug Status:

      INN, BAN Microsource [01503094]
    • Compound Source:

      synthetic Microsource [01503094]
    • Bio Activity:

      Antiseborrheic; Zerenex Molecular [ZBioX-0358]
      CA TargetMol T0515
      Carbonic Anhydrase MedChem Express HY-B0483
      Metabolism TargetMol T0515
      Others MedChem Express HY-B0483
      Tioxolone, a metalloenzyme carbonic anhydrase I inhibitor, is an anti-acne preparation. MedChem Express
      Tioxolone, a metalloenzyme carbonic anhydrase I inhibitor, is an anti-acne preparation.; Target: Carbonic Anhydrase ; Tioxolone is a metalloenzyme carbonic anhydrase I inhibitor with a Ki of 91 nM. MedChem Express HY-B0483
      Tioxolone, a metalloenzyme carbonic anhydrase I inhibitor, is an anti-acne preparation.;Target: Carbonic Anhydrase ;Tioxolone is a metalloenzyme carbonic anhydrase I inhibitor with a Ki of 91 nM. Tioxolone lacks sulfonamide, sulfamate, or hydroxamate functional groups that are typically found in therapeutic carbonic anhydrase (CA) inhibitors, such as acetazolamide. Tioxolone is proposed to be a prodrug inhibitor that is cleaved via a CA II zinc-hydroxide mechanism known to catalyze the hydrolysis of esters. When tioxolone binds in the active site of CA II, it is cleaved and forms 4-mercaptobenzene-1,3-diol via the intermediate S-(2,4-thiophenyl) hydrogen thiocarbonate. The esterase cleavage product binds to the zinc active site via the thiol group and is therefore the active CA inhibitor, while the intermediate is located at the rim of the active-site cavity. From Wikipedia. MedChem Express HY-B0483
  • Gas Chromatography

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

Density: 1.6±0.1 g/cm3
Boiling Point: 377.8±44.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 65.0±3.0 kJ/mol
Flash Point: 182.3±28.4 °C
Index of Refraction: 1.718
Molar Refractivity: 41.0±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 1.77
ACD/LogD (pH 5.5): 1.63
ACD/BCF (pH 5.5): 10.25
ACD/KOC (pH 5.5): 184.01
ACD/LogD (pH 7.4): 1.56
ACD/BCF (pH 7.4): 8.69
ACD/KOC (pH 7.4): 155.95
Polar Surface Area: 72 Å2
Polarizability: 16.2±0.5 10-24cm3
Surface Tension: 74.5±3.0 dyne/cm
Molar Volume: 104.0±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) =  1.67

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  339.00  (Adapted Stein & Brown method)
    Melting Pt (deg C):  112.00  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.78E-006  (Modified Grain method)
    MP  (exp database):  160 deg C
    Subcooled liquid VP: 6.74E-005 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):  9005
       log Kow used: 1.67 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  12061 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.71E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.831E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.67  (KowWin est)
  Log Kaw used:  -6.501  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.171
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7833
   Biowin2 (Non-Linear Model)     :   0.8219
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8839  (weeks       )
   Biowin4 (Primary Survey Model) :   3.6448  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3007
   Biowin6 (MITI Non-Linear Model):   0.1854
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6305
 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):  0.00899 Pa (6.74E-005 mm Hg)
  Log Koa (Koawin est  ): 8.171
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000334 
       Octanol/air (Koa) model:  3.64E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0119 
       Mackay model           :  0.026 
       Octanol/air (Koa) model:  0.0029 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  19.6839 E-12 cm3/molecule-sec
      Half-Life =     0.543 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     6.521 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.019 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  164.9
      Log Koc:  2.217 

 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 = 0.583 (BCF = 3.829)
       log Kow used: 1.67 (estimated)

 Volatilization from Water:
    Henry LC:  7.71E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.848E+004  hours   (4103 days)
    Half-Life from Model Lake : 1.074E+006  hours   (4.477E+004 days)

 Removal In Wastewater Treatment:
    Total removal:               2.03  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.94  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       0.145           13           1000       
   Water     27.8            360          1000       
   Soil      72              720          1000       
   Sediment  0.0733          3.24e+003    0          
     Persistence Time: 626 hr


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