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ChemSpider 2D Image | Eicosapentanoic acid | C20H30O2

Eicosapentanoic acid

  • Molecular FormulaC20H30O2
  • Average mass302.451 Da
  • Monoisotopic mass302.224579 Da
  • ChemSpider ID393682

  • Double-bond stereo - Double-bond stereo

More details:

Featured data source
The Merck Index Online

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

(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acid
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Icosapentaenoic acid [ACD/IUPAC Name]
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Icosapentaensäure [German] [ACD/IUPAC Name]
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acid
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid
10417-94-4 [RN]
1714433 [Beilstein]
5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)- [ACD/Index Name]
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid
More...

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

6328 [DBID]
CHEBI:28364 [DBID]
44864_FLUKA [DBID]
62160_FLUKA [DBID]
62170_FLUKA [DBID]
AIDS082784 [DBID]
AIDS-082784 [DBID]
BSPBio_001376 [DBID]
C06427 [DBID]
C06428 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      An icosapentaenoic acid having five <stereo>cis</stereo>-double bonds at positions 5, 8, 11, 14 and 17. ChEBI CHEBI:28364
      An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28364, CHEBI:28364

    • Bio Activity:

      Eicosapentaenoic acid (EPA) is an omega-3 fatty acid. MedChem Express
      Eicosapentaenoic acid (EPA) is an omega-3 fatty acid.; Target: Others; Studies have suggested that EPA may be efficacious in treating depression. MedChem Express HY-B0660
      Eicosapentaenoic acid (EPA) is an omega-3 fatty acid.;Target: Studies have suggested that EPA may be efficacious in treating depression. One 2004 study, took blood samples of 100 suicide attempt patients and compared the blood samples to those of controls and found that levels of eicosapentaenoic acid were significantly lower in the washed red blood cells of the suicide-attempt patients. A 2009 metastudy found that patients taking omega-3 supplements with a higher EPA:DHA ratio experienced fewer depressive symptoms. One study also reports the remission of depressive symptoms and decrease in lateral ventricular volume of a patient who suffers from chronic fatigue syndrome after taking high-EPA essential fatty acid supplement [1, 2]. MedChem Express HY-B0660
      Endogenous polyunsaturated fatty acid. Stimulates ERK1/2 and C/EBP? phosphorylation, and induces demethylation of CpG island B in U937 leukemia cells. Attenuates proliferation of U9137 cells, and induces cell cycle arrest and apoptosis in pancreatic cells in vitro. Also inhibits leukotriene B4 synthesis in rats. Tocris Bioscience 5979
      Endogenous polyunsaturated fatty acid. Stimulates ERK1/2 and C/EBPbeta phosphorylation, and induces demethylation of CpG island B in U937 leukemia cells. Attenuates proliferation of U9137 cells, and induces cell cycle arrest and apoptosis in pancreatic cells in vitro. Also inhibits leukotriene B4 synthesis in rats. Tocris Bioscience 5979
      Endogenous polyunsaturated fatty acid; stimulates ERK1/2 phosphorylation Tocris Bioscience 5979
      Enzymes Tocris Bioscience 5979
      Kinases Tocris Bioscience 5979
      MAPK Family Tocris Bioscience 5979
      Others MedChem Express HY-B0660
  • Gas Chromatography

    • Retention Index (Kovats):

      2406 (estimated with error: 51) NIST Spectra mainlib_336741, mainlib_333529

    • Retention Index (Linear):

      2334.2 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: Multi-step temperature program; T(initial)=60C; T(final)=270C; CAS no: 10417944; Active phase: VF-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., 2007.) NIST Spectra nist ri

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

Density: 0.9±0.1 g/cm3
Boiling Point: 439.3±24.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.3 mmHg at 25°C
Enthalpy of Vaporization: 76.3±6.0 kJ/mol
Flash Point: 336.0±18.0 °C
Index of Refraction: 1.513
Molar Refractivity: 96.6±0.3 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 13
#Rule of 5 Violations: 1
ACD/LogP: 6.23
ACD/LogD (pH 5.5): 4.91
ACD/BCF (pH 5.5): 2030.70
ACD/KOC (pH 5.5): 4747.92
ACD/LogD (pH 7.4): 3.12
ACD/BCF (pH 7.4): 32.41
ACD/KOC (pH 7.4): 75.78
Polar Surface Area: 37 Å2
Polarizability: 38.3±0.5 10-24cm3
Surface Tension: 35.7±3.0 dyne/cm
Molar Volume: 321.4±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) =  7.85

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  423.12  (Adapted Stein & Brown method)
    Melting Pt (deg C):  148.00  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.27E-007  (Modified Grain method)
    Subcooled liquid VP: 2.26E-006 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):  0.005814
       log Kow used: 7.85 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.044384 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.73E-005  atm-m3/mole
   Group Method:   1.86E-007  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  8.693E-006 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  7.85  (KowWin est)
  Log Kaw used:  -2.714  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.564
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7847
   Biowin2 (Non-Linear Model)     :   0.7686
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1937  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0660  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4511
   Biowin6 (MITI Non-Linear Model):   0.2090
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0982
 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):  0.000301 Pa (2.26E-006 mm Hg)
  Log Koa (Koawin est  ): 10.564
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00996 
       Octanol/air (Koa) model:  0.00899 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.264 
       Mackay model           :  0.443 
       Octanol/air (Koa) model:  0.418 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 290.7808 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 328.7808 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =   26.484 Min (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =   23.423 Min (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    65.000000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =   100.000000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =    25.388 Min (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =    16.502 Min (at 7E11 mol/cm3) [Trans-isomer]
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.354 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  3.97E+004
      Log Koc:  4.599 

 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: 7.85 (estimated)

 Volatilization from Water:
    Henry LC:  1.86E-007 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River:       5476  hours   (228.2 days)
    Half-Life from Model Lake : 5.989E+004  hours   (2495 days)

 Removal In Wastewater Treatment:
    Total removal:              94.01  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.23  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       0.011           0.286        1000       
   Water     3.81            360          1000       
   Soil      28.2            720          1000       
   Sediment  67.9            3.24e+003    0          
     Persistence Time: 1.23e+003 hr

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