ChemSpider 2D Image | subersic acid | C27H38O3

subersic acid

  • Molecular FormulaC27H38O3
  • Average mass410.589 Da
  • Monoisotopic mass410.282104 Da
  • ChemSpider ID9536819

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(+)-subersic acid
4-Hydroxy-3-{(2E)-3-methyl-5-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalenyl]-2-penten-1-yl}benzoic acid [ACD/IUPAC Name]
4-Hydroxy-3-{(2E)-3-methyl-5-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalinyl]-2-penten-1-yl}benzoesäure [German] [ACD/IUPAC Name]
Acide 4-hydroxy-3-{(2E)-3-méthyl-5-[(4aS,8aS)-2,5,5,8a-tétraméthyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphtalényl]-2-pentén-1-yl}benzoïque [French] [ACD/IUPAC Name]
Benzoic acid, 4-hydroxy-3-[(2E)-3-methyl-5-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-2-penten-1-yl]- [ACD/Index Name]
subersic acid
4-hydroxy-3-{(2E)-3-methyl-5-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]pent-2-en-1-yl}benzoic acid
CHEMBL455101
https://www.ebi.ac.uk/chembl/compoundreportcard/CHEMBL455101/
  • Miscellaneous

    • Chemical Class:

      A meroterpenoid that is 4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene substituted by a (3<stereo>E</stereo>)-5-(5-carboxy-2-hydroxyphenyl)-3-methylpent-3-en-1-yl moiety at position 8. It is isolated from the marine sponge <ital>Acanthodendrilla</ital> and exhibits inhibitory activity against the enzyme mitogen-activated protein kinase-activated protein kinase 2 (EC 2.7.11.1). ChEBI CHEBI:66532
      A meroterpenoid that is 4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene substituted by a (3E)-5-(5-carboxy-2-hydroxyphenyl)-3-methylpent-3-en-1-yl moiety at position 8. It is isolated from the marine sponge Acanthodendrilla and exhibits inhibitory activity against the enzyme mitogen-activated protein kinase-activated protein kinase 2 (EC 2.7.11.1). ChEBI CHEBI:66532
      A meroterpenoid that is 4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene substituted by a (3E)-5-(5-carboxy-2-hydroxyphenyl)-3-methylpent-3-en-1-yl moiety at position 8. It; is isolated fr om the marine sponge Acanthodendrilla and 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:66532

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

Density: 1.1±0.1 g/cm3
Boiling Point: 556.3±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 88.2±3.0 kJ/mol
Flash Point: 304.3±26.6 °C
Index of Refraction: 1.547
Molar Refractivity: 123.5±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 1
ACD/LogP: 9.93
ACD/LogD (pH 5.5): 7.95
ACD/BCF (pH 5.5): 363515.97
ACD/KOC (pH 5.5): 166828.59
ACD/LogD (pH 7.4): 6.28
ACD/BCF (pH 7.4): 7791.17
ACD/KOC (pH 7.4): 3575.60
Polar Surface Area: 58 Å2
Polarizability: 48.9±0.5 10-24cm3
Surface Tension: 39.5±3.0 dyne/cm
Molar Volume: 389.5±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) =  9.81

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  528.37  (Adapted Stein & Brown method)
    Melting Pt (deg C):  225.85  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.13E-012  (Modified Grain method)
    Subcooled liquid VP: 5.88E-010 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):  4.223e-005
       log Kow used: 9.81 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  8.7817e-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 :   6.71E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.284E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  9.81  (KowWin est)
  Log Kaw used:  -7.562  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.372
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5315
   Biowin2 (Non-Linear Model)     :   0.0863
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9370  (months      )
   Biowin4 (Primary Survey Model) :   2.9274  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2541
   Biowin6 (MITI Non-Linear Model):   0.0348
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.8742
 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):  7.84E-008 Pa (5.88E-010 mm Hg)
  Log Koa (Koawin est  ): 17.372
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  38.3 
       Octanol/air (Koa) model:  5.78E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 227.0108 E-12 cm3/molecule-sec
      Half-Life =     0.047 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.565 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =   131.725006 E-17 cm3/molecule-sec
      Half-Life =     0.009 Days (at 7E11 mol/cm3)
      Half-Life =     12.528 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    :  1.076E+006
      Log Koc:  6.032 

 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: 9.81 (estimated)

 Volatilization from Water:
    Henry LC:  6.71E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.768E+006  hours   (7.367E+004 days)
    Half-Life from Model Lake : 1.929E+007  hours   (8.037E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              94.04  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.26  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       0.00179         0.176        1000       
   Water     1.39            1.44e+003    1000       
   Soil      29.8            2.88e+003    1000       
   Sediment  68.9            1.3e+004     0          
     Persistence Time: 4.69e+003 hr

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