ChemSpider 2D Image | makassaric acid | C27H38O3

makassaric acid

  • Molecular FormulaC27H38O3
  • Average mass410.589 Da
  • Monoisotopic mass410.282104 Da
  • ChemSpider ID9467775

  • defined stereocentres - 5 of 5 defined stereocentres

More details:

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(+)-Makassaric acid
3-{[(14β)-8,13-Dimethylpodocarp-12-en-14-yl]methyl}-4-hydroxybenzoesäure [German] [ACD/IUPAC Name]
3-{[(14β)-8,13-Dimethylpodocarp-12-en-14-yl]methyl}-4-hydroxybenzoic acid [ACD/IUPAC Name]
Acide 3-{[(14β)-8,13-diméthylpodocarp-12-én-14-yl]méthyl}-4-hydroxybenzoïque [French] [ACD/IUPAC Name]
Benzoic acid, 3-[[(1R,4aR,4bS,8aS,10aS)-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethyl-1-phenanthrenyl]methyl]-4-hydroxy- [ACD/Index Name]
makassaric acid
4-hydroxy-3-{[(1R,4aR,4bS,8aS,10aS)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}benzoic acid
CHEMBL454582
https://www.ebi.ac.uk/chembl/compoundreportcard/CHEMBL454582/
  • Miscellaneous

    • Chemical Class:

      A meroterpenoid isolated from the marine sponge <ital>Acanthodendrilla</ital> sp. It exhibits inhibitory activity against the enzyme mitogen-activated protein kinase-activated protein kinase 2 (EC 2.7 .11.1). ChEBI CHEBI:66654
      A meroterpenoid isolated from the marine sponge Acanthodendrilla sp. It exhibits inhibitory activity against the enzyme mitogen-activated protein kinase-activated protein kinase 2 (EC 2.7.11.1). ChEBI CHEBI:66654
      A meroterpenoid isolated from the marine sponge Acanthodendrilla sp. It exhibits inhibitory activity against the enzyme mitogen-activated protein kinase-activated protein kinase 2 (EC 2.7; .11.1). ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:66654

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

Density: 1.1±0.1 g/cm3
Boiling Point: 535.1±43.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 85.4±3.0 kJ/mol
Flash Point: 291.5±24.7 °C
Index of Refraction: 1.554
Molar Refractivity: 121.5±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 1
ACD/LogP: 9.69
ACD/LogD (pH 5.5): 7.96
ACD/BCF (pH 5.5): 372035.44
ACD/KOC (pH 5.5): 171678.52
ACD/LogD (pH 7.4): 6.28
ACD/BCF (pH 7.4): 7881.73
ACD/KOC (pH 7.4): 3637.08
Polar Surface Area: 58 Å2
Polarizability: 48.2±0.5 10-24cm3
Surface Tension: 41.0±3.0 dyne/cm
Molar Volume: 378.9±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) =  8.85

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  519.15  (Adapted Stein & Brown method)
    Melting Pt (deg C):  221.54  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.38E-012  (Modified Grain method)
    Subcooled liquid VP: 1.06E-009 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):  0.0002746
       log Kow used: 8.85 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  6.0477e-005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.41E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.649E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  8.85  (KowWin est)
  Log Kaw used:  -8.006  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.856
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3476
   Biowin2 (Non-Linear Model)     :   0.0166
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7248  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.7739  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2675
   Biowin6 (MITI Non-Linear Model):   0.0218
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.3015
 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):  1.41E-007 Pa (1.06E-009 mm Hg)
  Log Koa (Koawin est  ): 16.856
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  21.2 
       Octanol/air (Koa) model:  1.76E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 122.9174 E-12 cm3/molecule-sec
      Half-Life =     0.087 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.044 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    43.000000 E-17 cm3/molecule-sec
      Half-Life =     0.027 Days (at 7E11 mol/cm3)
      Half-Life =     38.378 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.04E+006
      Log Koc:  6.310 

 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 = 1.000 (BCF = 10)
       log Kow used: 8.85 (estimated)

 Volatilization from Water:
    Henry LC:  2.41E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.923E+006  hours   (2.051E+005 days)
    Half-Life from Model Lake :  5.37E+007  hours   (2.238E+006 days)

 Removal In Wastewater Treatment:
    Total removal:              94.03  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.25  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       0.00212         0.49         1000       
   Water     0.747           4.32e+003    1000       
   Soil      39.6            8.64e+003    1000       
   Sediment  59.6            3.89e+004    0          
     Persistence Time: 1.07e+004 hr

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