ChemSpider 2D Image | (+)-cucurbic acid | C12H20O3

(+)-cucurbic acid

  • Molecular FormulaC12H20O3
  • Average mass212.285 Da
  • Monoisotopic mass212.141251 Da
  • ChemSpider ID4444599

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 3 of 3 defined stereocentres

More details:

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

(+)-cucurbic acid
{(1R,2S,3S)-3-Hydroxy-2-[(2Z)-2-penten-1-yl]cyclopentyl}acetic acid [ACD/IUPAC Name]
{(1R,2S,3S)-3-Hydroxy-2-[(2Z)-2-penten-1-yl]cyclopentyl}essigsäure [German] [ACD/IUPAC Name]
131488-83-0 [RN]
58240-50-9 [RN]
Acide {(1R,2S,3S)-3-hydroxy-2-[(2Z)-2-pentén-1-yl]cyclopentyl}acétique [French] [ACD/IUPAC Name]
Cyclopentaneacetic acid, 3-hydroxy-2-[(2Z)-2-penten-1-yl]-, (1R,2S,3S)- [ACD/Index Name]
(±)-3-HYDROXY-2-(2-PENTENYL)CYCLOPENTANEACETIC ACID
(±)-3-HYDROXY-2-(2-PENTENYL)CYCLOPENTANEACETICACID
(±)-Cucurbic acid
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

5477675 [DBID]
C08482 [DBID]

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

Density: 1.1±0.1 g/cm3
Boiling Point: 364.5±15.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 70.7±6.0 kJ/mol
Flash Point: 188.4±16.9 °C
Index of Refraction: 1.504
Molar Refractivity: 58.8±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 2.02
ACD/LogD (pH 5.5): 1.20
ACD/BCF (pH 5.5): 2.96
ACD/KOC (pH 5.5): 42.26
ACD/LogD (pH 7.4): -0.60
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 58 Å2
Polarizability: 23.3±0.5 10-24cm3
Surface Tension: 41.3±3.0 dyne/cm
Molar Volume: 198.6±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) =  2.99

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  353.07  (Adapted Stein & Brown method)
    Melting Pt (deg C):  118.53  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.04E-007  (Modified Grain method)
    Subcooled liquid VP: 4.26E-006 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):  857.4
       log Kow used: 2.99 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2814.5 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 :   1.32E-010  atm-m3/mole
   Group Method:   7.73E-012  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.642E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.99  (KowWin est)
  Log Kaw used:  -8.268  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.258
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9863
   Biowin2 (Non-Linear Model)     :   0.9734
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.5529  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.3255  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6607
   Biowin6 (MITI Non-Linear Model):   0.4964
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5676
 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):  0.000568 Pa (4.26E-006 mm Hg)
  Log Koa (Koawin est  ): 11.258
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00528 
       Octanol/air (Koa) model:  0.0445 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.16 
       Mackay model           :  0.297 
       Octanol/air (Koa) model:  0.781 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  73.1758 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =  80.7758 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.754 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.589 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    13.000000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    20.000000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     2.116 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.375 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.229 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  14.23
      Log Koc:  1.153 

 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: 2.99 (estimated)

 Volatilization from Water:
    Henry LC:  7.73E-012 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 1.104E+008  hours   (4.598E+006 days)
    Half-Life from Model Lake : 1.204E+009  hours   (5.016E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               5.61  percent
    Total biodegradation:        0.12  percent
    Total sludge adsorption:     5.48  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       0.000276        1.32         1000       
   Water     18.8            208          1000       
   Soil      81              416          1000       
   Sediment  0.233           1.87e+003    0          
     Persistence Time: 462 hr

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