ChemSpider 2D Image | Cantharidin | C10H12O4

Cantharidin

  • Molecular FormulaC10H12O4
  • Average mass196.200 Da
  • Monoisotopic mass196.073563 Da
  • ChemSpider ID5731
  • defined stereocentres - 4 of 4 defined stereocentres


More details:



Featured data source



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

(1R,2S,6R,7S)-2,6-Dimethyl-4,10-dioxatricyclo[5.2.1.02,6]decan-3,5-dion [German] [ACD/IUPAC Name]
(1R,2S,6R,7S)-2,6-Dimethyl-4,10-dioxatricyclo[5.2.1.02,6]decane-3,5-dione [ACD/IUPAC Name]
(1R,2S,6R,7S)-2,6-Diméthyl-4,10-dioxatricyclo[5.2.1.02,6]décane-3,5-dione [French] [ACD/IUPAC Name]
(3ar,4s,7r,7as)-3a,7a-dimethylhexahydro-4,7-epoxy-2-benzofuran-1,3-dione
4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aR,4S,7R,7aS)- [ACD/Index Name]
4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aα,4β,7β,7aα)-
4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aα,4β,7β,7aα)-
56-25-7 [RN]
Cantharidin [Wiki]
(1R,2S,3R,6S)-1,2-Dimethyl-3,6-epoxycyclohexane-1,2-dicarboxylic anhydride
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:64213 [DBID]
AI3-04021 [DBID]
AIDS014422 [DBID]
AIDS-014422 [DBID]
BRN 0085302 [DBID]
Caswell No. 157 [DBID]
CCRIS 635 [DBID]
EPA Pesticide Chemical Code 013101 [DBID]
HSDB 2181 [DBID]
NCGC00016247-01 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      Others TargetMol T2903
    • Bio Activity:

      Cantharidin, a natural toxin isolated from beetles in the families Meloidae and Oedemeridae, has been reported to be toxic to some pests, including the diamondback moth.; IC50 value:; Target:; In vitr o: A 48 h treatment of human erythrocytes with cantharidin significantly increased the percentage of annexin-V-binding cells (?10 ?g/mL), significantly decreased forward scatter (?25 ?g/mL), significa ntly increased [Ca2+]i (?25 ?g/mL), but did not significantly modify ceramide abundance or ROS [1]. MedChem Express HY-N0209
      Enzymes Tocris Bioscience 1548
      Natural toxin inhibitor of protein phosphatases 1 and 2A (Ki values are 1.1 and 0.19 ?M respectively); similar to okadaic acid (Cat. No. 1136). Displays > 500-fold selectivity over PP2B. Tocris Bioscience 1548
      Others MedChem Express HY-N0209
      Others TargetMol T2903
      Phosphatases Tocris Bioscience 1548
      Protein phosphatase 1 and 2A inhibitor Tocris Bioscience 1548
      Protein Ser/Thr Phosphatases Tocris Bioscience 1548
  • Gas Chromatography
    • Retention Index (Kovats):

      1457 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column diameter: 0.53 mm; Column length: 25 m; Column type: Capillary; Start T: 130 C; CAS no: 56257; Active phase: BP-1; Carrier gas: N2; Phase thickness: 1 um; Data type: Kovats RI; Authors: Japp, M.; Gill, R.; Osselton, M.D., Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns, J. Forensic Sci., 32(6), 1987, 1574-1586.) NIST Spectra nist ri
      1468 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column diameter: 0.53 mm; Column length: 30 m; Column type: Capillary; Start T: 130 C; CAS no: 56257; Active phase: DB-1; Carrier gas: N2; Phase thickness: 1.5 um; Data type: Kovats RI; Authors: Japp, M.; Gill, R.; Osselton, M.D., Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns, J. Forensic Sci., 32(6), 1987, 1574-1586.) NIST Spectra nist ri
      1472 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column diameter: 0.22 mm; Column length: 25 m; Column type: Capillary; Start T: 130 C; CAS no: 56257; Active phase: BP-1; Carrier gas: N2; Phase thickness: 0.25 um; Data type: Kovats RI; Authors: Japp, M.; Gill, R.; Osselton, M.D., Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns, J. Forensic Sci., 32(6), 1987, 1574-1586.) NIST Spectra nist ri
    • Retention Index (Normal Alkane):

      1490 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 56257; Active phase: Methyl Silicone; Data type: Normal alkane RI; Authors: Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 220, 1981, 195-252.) NIST Spectra nist ri

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

Density: 1.4±0.1 g/cm3
Boiling Point: 326.9±35.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.7 mmHg at 25°C
Enthalpy of Vaporization: 56.9±3.0 kJ/mol
Flash Point: 146.1±26.0 °C
Index of Refraction: 1.547
Molar Refractivity: 45.7±0.3 cm3
#H bond acceptors: 4
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 0.10
ACD/LogD (pH 5.5): 0.37
ACD/BCF (pH 5.5): 1.12
ACD/KOC (pH 5.5): 37.65
ACD/LogD (pH 7.4): 0.37
ACD/BCF (pH 7.4): 1.12
ACD/KOC (pH 7.4): 37.65
Polar Surface Area: 53 Å2
Polarizability: 18.1±0.5 10-24cm3
Surface Tension: 49.2±3.0 dyne/cm
Molar Volume: 144.0±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) =  1.22

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  266.86  (Adapted Stein & Brown method)
    Melting Pt (deg C):  58.55  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.71E-005  (Modified Grain method)
    MP  (exp database):  218 deg C
    Subcooled liquid VP: 0.0111 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):  4138
       log Kow used: 1.22 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  30 mg/L (20 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  28318 mg/L
    Wat Sol (Exper. database match) =  30.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.86E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.058E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.22  (KowWin est)
  Log Kaw used:  -6.119  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.339
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.0611
   Biowin2 (Non-Linear Model)     :   0.0013
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3327  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2480  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3303
   Biowin6 (MITI Non-Linear Model):   0.1002
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4099
 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):  1.48 Pa (0.0111 mm Hg)
  Log Koa (Koawin est  ): 7.339
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.03E-006 
       Octanol/air (Koa) model:  5.36E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  7.32E-005 
       Mackay model           :  0.000162 
       Octanol/air (Koa) model:  0.000428 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  16.8099 E-12 cm3/molecule-sec
      Half-Life =     0.636 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     7.635 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.000118 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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 = 0.241 (BCF = 1.742)
       log Kow used: 1.22 (estimated)

 Volatilization from Water:
    Henry LC:  1.86E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.409E+004  hours   (1837 days)
    Half-Life from Model Lake : 4.811E+005  hours   (2.005E+004 days)

 Removal In Wastewater Treatment:
    Total removal:               1.91  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.82  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       0.191           15.3         1000       
   Water     39.4            900          1000       
   Soil      60.4            1.8e+003     1000       
   Sediment  0.088           8.1e+003     0          
     Persistence Time: 966 hr




                    

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