ChemSpider 2D Image | (1R,3R,3aS,4S,5R,7aS)-3,4,5,7-Tetraethyl-1-methyl-2-oxo-5-[(E)-2-phenylvinyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid | C27H36O3

(1R,3R,3aS,4S,5R,7aS)-3,4,5,7-Tetraethyl-1-methyl-2-oxo-5-[(E)-2-phenylvinyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid

  • Molecular FormulaC27H36O3
  • Average mass408.573 Da
  • Monoisotopic mass408.266449 Da
  • ChemSpider ID9456261
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 6 of 6 defined stereocentres


More details:






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

(1R,3R,3aS,4S,5R,7aS)-3,4,5,7-Tetraethyl-1-methyl-2-oxo-5-[(E)-2-phenylvinyl]-2,3,3a,4,5,7a-hexahydro-1H-inden-4-carbonsäure [German] [ACD/IUPAC Name]
(1R,3R,3aS,4S,5R,7aS)-3,4,5,7-Tetraethyl-1-methyl-2-oxo-5-[(E)-2-phenylvinyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid [ACD/IUPAC Name]
1H-Indene-4-carboxylic acid, 3,4,5,7-tetraethyl-2,3,3a,4,5,7a-hexahydro-1-methyl-2-oxo-5-[(E)-2-phenylethenyl]-, (1R,3R,3aS,4S,5R,7aS)- [ACD/Index Name]
910333-81-2 [RN]
Acide (1R,3R,3aS,4S,5R,7aS)-3,4,5,7-tétraéthyl-1-méthyl-2-oxo-5-[(E)-2-phénylvinyl]-2,3,3a,4,5,7a-hexahydro-1H-indène-4-carboxylique [French] [ACD/IUPAC Name]
spiculoic acid A
(1R,3R,3aS,4S,5R,7aS)-3,4,5,7-tetraethyl-1-methyl-2-oxo-5-[(E)-2-phenylethenyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid
  • Miscellaneous
    • Chemical Class:

      A carbobicyclic compound that is 2,3,3a,4,5,7a-hexahydro-1<element>H</element>-indene substituted by ethyl groups at positions 3, 4, 5 and 7, a methyl group at position 1, an oxo group at position 2, a 2-phenylethenyl group at position 5 and a carboxy group at position 4 (the 1<stereo>R</stereo>,3<stereo>R</stereo>,3a<stereo>S</stereo>,4<stereo>S</stereo>,5<stereo>R</stereo>,7a<stereo>S</stereo> s tereoisomer). Isolated from <ital>Plakortis angulospiculatus</ital>, it exhibits cytotoxicity against human breast cancer MCF-7 cells. ChEBI CHEBI:66520
      A carbobicyclic compound that is 2,3,3a,4,5,7a-hexahydro-1H-indene substituted by ethyl groups at positions 3, 4, 5 and 7, a methyl group at position 1, an oxo group at position 2, ; a 2-phenylethenyl group at position 5 and a carboxy group at position 4 (the 1R,3R,3aS,4S,5R,7aS s; tereoisomer). Isolated from Plakortis angulospiculatus, it exhibits cytotoxicity against human breast cancer MCF-7 ce lls. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:66520

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.1±0.1 g/cm3
Boiling Point: 543.2±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 86.5±3.0 kJ/mol
Flash Point: 296.4±26.6 °C
Index of Refraction: 1.558
Molar Refractivity: 124.5±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 1
ACD/LogP: 7.27
ACD/LogD (pH 5.5): 5.66
ACD/BCF (pH 5.5): 5773.82
ACD/KOC (pH 5.5): 7398.75
ACD/LogD (pH 7.4): 3.88
ACD/BCF (pH 7.4): 96.09
ACD/KOC (pH 7.4): 123.13
Polar Surface Area: 54 Å2
Polarizability: 49.3±0.5 10-24cm3
Surface Tension: 39.8±3.0 dyne/cm
Molar Volume: 386.0±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) =  7.62

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  519.28  (Adapted Stein & Brown method)
    Melting Pt (deg C):  221.61  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.03E-011  (Modified Grain method)
    Subcooled liquid VP: 8.9E-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):  0.002095
       log Kow used: 7.62 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.0024949 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 :   3.07E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.804E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  7.62  (KowWin est)
  Log Kaw used:  -7.901  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.521
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3928
   Biowin2 (Non-Linear Model)     :   0.0141
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2361  (months      )
   Biowin4 (Primary Survey Model) :   3.3196  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2399
   Biowin6 (MITI Non-Linear Model):   0.0108
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6531
 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):  1.19E-006 Pa (8.9E-009 mm Hg)
  Log Koa (Koawin est  ): 15.521
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.53 
       Octanol/air (Koa) model:  815 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.989 
       Mackay model           :  0.995 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 169.5629 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 177.1629 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.757 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.724 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     8.443749 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     9.493750 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     3.257 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     2.897 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.992 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.751E+005
      Log Koc:  5.243 

 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: 7.62 (estimated)

 Volatilization from Water:
    Henry LC:  3.07E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.855E+006  hours   (1.606E+005 days)
    Half-Life from Model Lake : 4.205E+007  hours   (1.752E+006 days)

 Removal In Wastewater Treatment:
    Total removal:              93.99  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.21  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       0.00905         1.03         1000       
   Water     1.4             1.44e+003    1000       
   Soil      31.6            2.88e+003    1000       
   Sediment  67              1.3e+004     0          
     Persistence Time: 4.82e+003 hr




                    

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