ChemSpider 2D Image | Eunicea sesquiterpenoid 7 | C20H28O5

Eunicea sesquiterpenoid 7

  • Molecular FormulaC20H28O5
  • Average mass348.433 Da
  • Monoisotopic mass348.193665 Da
  • ChemSpider ID9877727

  • 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

(1S,2E,10R)-10-Acetyl-3-methyl-7-methylen-6-oxo-2-cyclodecen-1-yl-(2E)-4-hydroxy-4-methyl-2-pentenoat [German] [ACD/IUPAC Name]
(1S,2E,10R)-10-Acetyl-3-methyl-7-methylene-6-oxo-2-cyclodecen-1-yl (2E)-4-hydroxy-4-methyl-2-pentenoate [ACD/IUPAC Name]
(2E)-4-Hydroxy-4-méthyl-2-penténoate de (1S,2E,10R)-10-acétyl-3-méthyl-7-méthylène-6-oxo-2-cyclodécén-1-yle [French] [ACD/IUPAC Name]
2-Pentenoic acid, 4-hydroxy-4-methyl-, (1S,2E,10R)-10-acetyl-3-methyl-7-methylene-6-oxo-2-cyclodecen-1-yl ester, (2E)- [ACD/Index Name]
Eunicea sesquiterpenoid 7
(1S,2E,10R)-10-acetyl-3-methyl-7-methylidene-6-oxocyclodec-2-en-1-yl (2E)-4-hydroxy-4-methylpent-2-enoate
(E)-((1S,10R,E)-10-acetyl-3-methyl-7-methylene-6-oxocyclodec-2-enyl) 4-hydroxy-4-methylpent-2-enoate
https://www.ebi.ac.uk/chembl/compoundreportcard/CHEMBL465964/
  • Miscellaneous

    • Chemical Class:

      A sesquiterpenoid that is a carboxylic ester obtained by the formal condensation of the 6-hydroxy group of cyclodec-4-en-1-one which is also substituted by an acetyl, a methyl and a methylidene group at positions 7, 4 and 10 respectively with the carboxy group of pent-2-enoic acid substituted with a hydroxy and a methyl group at position 4. It is an antiplasmodial drug isolated from a Caribbean go rgonian coral <ital>Eunicea</ital> sp. ChEBI CHEBI:65877
      A sesquiterpenoid that is a carboxylic ester obtained by the formal condensation of the 6-hydroxy group of cyclodec-4-en-1-one which is also substituted by an acetyl, a methyl and a methylidene group at positions 7, 4 and 10 respectively with the carboxy group of pent-2-enoic acid substituted with a hydroxy and a methyl group at position 4. It is an antiplasmodial drug isolated from a Caribbean go rgonian coral Eunicea sp. ChEBI CHEBI:65877

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

Density: 1.1±0.1 g/cm3
Boiling Point: 504.0±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.9 mmHg at 25°C
Enthalpy of Vaporization: 89.1±6.0 kJ/mol
Flash Point: 171.7±23.6 °C
Index of Refraction: 1.515
Molar Refractivity: 95.3±0.4 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 2.51
ACD/LogD (pH 5.5): 2.81
ACD/BCF (pH 5.5): 80.26
ACD/KOC (pH 5.5): 803.27
ACD/LogD (pH 7.4): 2.81
ACD/BCF (pH 7.4): 80.26
ACD/KOC (pH 7.4): 803.27
Polar Surface Area: 81 Å2
Polarizability: 37.8±0.5 10-24cm3
Surface Tension: 41.7±5.0 dyne/cm
Molar Volume: 316.3±5.0 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) =  2.62

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  445.95  (Adapted Stein & Brown method)
    Melting Pt (deg C):  172.71  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.38E-010  (Modified Grain method)
    Subcooled liquid VP: 8.05E-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):  118.2
       log Kow used: 2.62 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  389.62 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylates
       Vinyl/Allyl Ketones
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.16E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.232E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.62  (KowWin est)
  Log Kaw used:  -12.324  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.944
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5856
   Biowin2 (Non-Linear Model)     :   0.3802
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3123  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3761  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4587
   Biowin6 (MITI Non-Linear Model):   0.1077
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.1971
 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):  1.07E-006 Pa (8.05E-009 mm Hg)
  Log Koa (Koawin est  ): 14.944
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.8 
       Octanol/air (Koa) model:  216 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.99 
       Mackay model           :  0.996 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 178.7519 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 181.4119 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.718 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.708 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    44.225002 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    44.312500 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     0.622 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     0.621 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.993 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  25.72
      Log Koc:  1.410 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.051E-004  L/mol-sec
  Kb Half-Life at pH 8:     107.076  years  
  Kb Half-Life at pH 7:    1070.760  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.319 (BCF = 20.83)
       log Kow used: 2.62 (estimated)

 Volatilization from Water:
    Henry LC:  1.16E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.421E+010  hours   (3.926E+009 days)
    Half-Life from Model Lake : 1.028E+012  hours   (4.282E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               3.49  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.38  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       1.23e-005       0.434        1000       
   Water     15              900          1000       
   Soil      84.9            1.8e+003     1000       
   Sediment  0.154           8.1e+003     0          
     Persistence Time: 1.69e+003 hr

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