ChemSpider 2D Image | (1R,2S,3R,4S)-2,3-Dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid | C10H14O5

(1R,2S,3R,4S)-2,3-Dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid

  • Molecular FormulaC10H14O5
  • Average mass214.215 Da
  • Monoisotopic mass214.084122 Da
  • ChemSpider ID108402

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

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

(1R,2S,3R,4S)-2,3-Dimethyl-7-oxabicyclo[2.2.1]heptan-2,3-dicarbonsäure [German] [ACD/IUPAC Name]
(1R,2S,3R,4S)-2,3-Dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid [ACD/IUPAC Name]
28874-45-5 [RN]
7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid, 2,3-dimethyl-, (1R,2S,3R,4S)- [ACD/Index Name]
Acide (1R,2S,3R,4S)-2,3-diméthyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylique [French] [ACD/IUPAC Name]
rel-(1R,2S,3R,4S)-2,3-Dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid
2,3-Dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid [ACD/IUPAC Name]
7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid, 2,3-dimethyl-, (1R,2S,3R,4S)-rel-
Cantharidic Acid
NHC

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

C8088_SIGMA [DBID]
Lopac-C-8088 [DBID]
NCGC00015272-01 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A monoterpenoid with an epoxy-bridged bicyclic dicarboxylic acid structure, which acts as an inhibitor of protein phosphatases 1 and 2A. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:78695, CHEBI:78695

    • Bio Activity:

      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB0167
      Enzymes/Phosphatase/Phosphoprotein phosphatase/PP2A Hello Bio HB0167
      Potent and selective protein phosphatase 2A (PP2A) inhibitor (IC<sub>50</sub> = 53 nM). Selective for PP2A over PP1 (IC<sub>50</sub> = 562 nM). Potentiates cyclic-AMP Response element binding (CREB) signalling (EC<sub>50</sub> = 0.45 &micro;M). Increases transduction of adenovirus vectors. Shows apoptotic actions. Hello Bio HB0167
      Potent, selective PP2A inhibitor Hello Bio HB0167

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

Density: 1.4±0.1 g/cm3
Boiling Point: 407.8±40.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 72.4±6.0 kJ/mol
Flash Point: 164.1±20.8 °C
Index of Refraction: 1.531
Molar Refractivity: 48.8±0.3 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 0.62
ACD/LogD (pH 5.5): -0.96
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.01
ACD/LogD (pH 7.4): -3.43
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 84 Å2
Polarizability: 19.3±0.5 10-24cm3
Surface Tension: 52.7±3.0 dyne/cm
Molar Volume: 157.6±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) =  2.80

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  360.83  (Adapted Stein & Brown method)
    Melting Pt (deg C):  147.37  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.17E-006  (Modified Grain method)
    Subcooled liquid VP: 7.3E-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):  372.8
       log Kow used: 2.80 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  50002 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 :   6.39E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.153E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.80  (KowWin est)
  Log Kaw used:  -12.583  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.383
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.0757
   Biowin2 (Non-Linear Model)     :   0.0036
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0221  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9932  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6390
   Biowin6 (MITI Non-Linear Model):   0.3904
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0364
 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):  0.00973 Pa (7.3E-005 mm Hg)
  Log Koa (Koawin est  ): 15.383
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000308 
       Octanol/air (Koa) model:  593 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.011 
       Mackay model           :  0.0241 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  17.8499 E-12 cm3/molecule-sec
      Half-Life =     0.599 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     7.191 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.0175 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  17.73
      Log Koc:  1.249 

 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: 2.80 (estimated)

 Volatilization from Water:
    Henry LC:  6.39E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.341E+011  hours   (5.588E+009 days)
    Half-Life from Model Lake : 1.463E+012  hours   (6.096E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               4.31  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     4.20  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       1.15e-007       14.4         1000       
   Water     17.4            360          1000       
   Soil      82.4            720          1000       
   Sediment  0.202           3.24e+003    0          
     Persistence Time: 768 hr

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