ChemSpider 2D Image | ballotenic acid | C20H30O4

ballotenic acid

  • Molecular FormulaC20H30O4
  • Average mass334.450 Da
  • Monoisotopic mass334.214417 Da
  • ChemSpider ID8172609

  • defined stereocentres - 4 of 5 defined stereocentres

More details:

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

(4aR,5S,6R,8aR)-5,6,8a-Trimethyl-5-[2-(2-oxotetrahydro-3-furanyl)ethyl]-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalenecarboxylic acid [ACD/IUPAC Name]
(4aR,5S,6R,8aR)-5,6,8a-Trimethyl-5-[2-(2-oxotetrahydro-3-furanyl)ethyl]-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalincarbonsäure [German] [ACD/IUPAC Name]
1-Naphthalenecarboxylic acid, 3,4,4a,5,6,7,8,8a-octahydro-5,6,8a-trimethyl-5-[2-(tetrahydro-2-oxo-3-furanyl)ethyl]-, (4aR,5S,6R,8aR)- [ACD/Index Name]
Acide (4aR,5S,6R,8aR)-5,6,8a-triméthyl-5-[2-(2-oxotétrahydro-3-furanyl)éthyl]-3,4,4a,5,6,7,8,8a-octahydro-1-naphtalènecarboxylique [French] [ACD/IUPAC Name]
ballotenic acid
(4aR,5S,6R,8aR)-5,6,8a-trimethyl-5-[2-(2-oxotetrahydrofuran-3-yl)ethyl]-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid
  • Miscellaneous

    • Chemical Class:

      A diterpenoid that is 3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid substituted by methyl groups at positions 5, 6 and 8a and a 2-(2-oxotetrahydrofuran-3-yl)ethyl group at position 5 (the 4 a<stereo>R</stereo>,5<stereo>S</stereo>,6<stereo>R</stereo>,8a<stereo>R</stereo> stereoisomer). It is isolated from the whole plant of <ital>Ballota limbata</ital> (Syn.<ital>Otostegia limbata</ital>) and acts as a lipoxygenase inhibitor. ChEBI CHEBI:65462
      A diterpenoid that is 3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid substituted by methyl groups at positions 5, 6 and 8a and a 2-(2-oxotetrahydrofuran-3-yl)ethyl group at position 5 (the 4 aR,5S,6R,8aR stereoisomer). It is isolated from the whole plant of Ballota limbata (Syn.Otostegia limbata) and acts as a lipoxygenase inhibitor. ChEBI CHEBI:65462
      A diterpenoid that is 3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid substituted by methyl groups at positions 5, 6 and 8a and a 2-(2-oxotetrahydrofuran-3-yl)ethyl group at position 5 (the 4 aR,5S,6R,8aR stereoisomer). It is isolated from the whole plant of Ballota limbata (Syn.Otostegia limbata); and acts as a lipoxygenase inhibitor. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65462

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

Density: 1.1±0.1 g/cm3
Boiling Point: 496.7±18.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 83.7±6.0 kJ/mol
Flash Point: 171.9±14.7 °C
Index of Refraction: 1.511
Molar Refractivity: 91.3±0.3 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 4.45
ACD/LogD (pH 5.5): 3.43
ACD/BCF (pH 5.5): 159.87
ACD/KOC (pH 5.5): 814.15
ACD/LogD (pH 7.4): 1.65
ACD/BCF (pH 7.4): 2.61
ACD/KOC (pH 7.4): 13.31
Polar Surface Area: 64 Å2
Polarizability: 36.2±0.5 10-24cm3
Surface Tension: 38.7±3.0 dyne/cm
Molar Volume: 305.0±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) =  4.80

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  468.02  (Adapted Stein & Brown method)
    Melting Pt (deg C):  195.15  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.84E-009  (Modified Grain method)
    Subcooled liquid VP: 1.75E-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):  1.505
       log Kow used: 4.80 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.20971 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.76E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.304E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.80  (KowWin est)
  Log Kaw used:  -6.628  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.428
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4673
   Biowin2 (Non-Linear Model)     :   0.3859
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5406  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6728  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6392
   Biowin6 (MITI Non-Linear Model):   0.3155
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3357
 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):  2.33E-005 Pa (1.75E-007 mm Hg)
  Log Koa (Koawin est  ): 11.428
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.129 
       Octanol/air (Koa) model:  0.0658 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.823 
       Mackay model           :  0.911 
       Octanol/air (Koa) model:  0.84 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  48.8591 E-12 cm3/molecule-sec
      Half-Life =     0.219 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.627 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   Fraction sorbed to airborne particulates (phi): 0.867 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  3673
      Log Koc:  3.565 

 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: 4.80 (estimated)

 Volatilization from Water:
    Henry LC:  5.76E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.859E+005  hours   (7746 days)
    Half-Life from Model Lake : 2.028E+006  hours   (8.45E+004 days)

 Removal In Wastewater Treatment:
    Total removal:              70.37  percent
    Total biodegradation:        0.63  percent
    Total sludge adsorption:    69.74  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       0.0842          4.32         1000       
   Water     11.5            900          1000       
   Soil      71.6            1.8e+003     1000       
   Sediment  16.9            8.1e+003     0          
     Persistence Time: 1.56e+003 hr

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