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ChemSpider 2D Image | (all-Z)-20-hydroxy-5,8,11,14-Eicosatetraenoic acid | C20H32O3

(all-Z)-20-hydroxy-5,8,11,14-Eicosatetraenoic acid

  • Molecular FormulaC20H32O3
  • Average mass320.466 Da
  • Monoisotopic mass320.235138 Da
  • ChemSpider ID4446281
  • Double-bond stereo - Double-bond stereo


More details:






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

(all-Z)-20-hydroxy-5,8,11,14-Eicosatetraenoic acid
(5Z,8Z,11Z,14Z)-20-Hydroxy-5,8,11,14-icosatetraenoic acid [ACD/IUPAC Name]
(5Z,8Z,11Z,14Z)-20-Hydroxy-5,8,11,14-icosatetraensäure [German] [ACD/IUPAC Name]
20-HETE
20-Hydroxyarachidonic acid
20-Hydroxyeicosatetraenoic acid [Wiki]
5,8,11,14-Eicosatetraenoic acid, 20-hydroxy-, (5Z,8Z,11Z,14Z)- [ACD/Index Name]
79551-86-3 [RN]
Acide (5Z,8Z,11Z,14Z)-20-hydroxy-5,8,11,14-icosatétraénoïque [French] [ACD/IUPAC Name]
MFCD00171542
More...

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

C14748 [DBID]
CHEBI:34306 [DBID]
H3023_SIGMA [DBID]
LMFA03060009 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A HETE that consists of arachidonic acid bearing a hydroxy substituent at position 20. ChEBI CHEBI:34306, https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:34306
    • Bio Activity:

      20-HETE(20-hydroxy Arachidonic Acid) is a potent vasoconstrictor produced in vascular smooth muscle (VSM) cells. MedChem Express http://www.medchemexpress.com/Auristatin-E.html, HY-15598
      20-HETE(20-hydroxy Arachidonic Acid) is a potent vasoconstrictor produced in vascular smooth muscle (VSM) cells. It depolarizes VSM by blocking the open-state probability of Ca2+-activated K+-channels.;IC50 Value:;Target: 20-Hydroxyeicosatetraenoic acid (20-HETE) is a cytochrome P450-derived arachidonic acid metabolite that has been shown to increase smooth muscle contractions and proliferation, stimulate endothelial dysfunction and activation and promote hypertension. ;In vitro: Addition of 20-HETE to the bath (1-100 nM), reduced the frequency of opening of the large-conductance Ca(2+)-activated K+ channel recorded using cell-attached patches on VSM [1]. In kidney, 20-HETE induces diuresis by inhibiting Na+-K+-ATPase in proximal tubules and Na+/K+/Cl+ cotransporter in the thick ascending limb of Henle's loop [2].;In vivo: In Cyp4a14(-/-) mice, which display androgen-driven and 20-HETE-dependent hypertension, treatment with20-HETE antagonist abolished remodeling of renal resist MedChem Express HY-15598
      Membrane Tranporter/Ion Channel MedChem Express HY-15598
      Membrane Tranporter/Ion Channel; MedChem Express HY-15598
      Potassiun Channel MedChem Express HY-15598

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

Density: 1.0±0.1 g/cm3
Boiling Point: 482.0±33.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 86.1±6.0 kJ/mol
Flash Point: 259.4±21.9 °C
Index of Refraction: 1.515
Molar Refractivity: 98.0±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 15
#Rule of 5 Violations: 0
ACD/LogP: 4.91
ACD/LogD (pH 5.5): 4.09
ACD/BCF (pH 5.5): 478.34
ACD/KOC (pH 5.5): 1686.78
ACD/LogD (pH 7.4): 2.29
ACD/BCF (pH 7.4): 7.64
ACD/KOC (pH 7.4): 26.92
Polar Surface Area: 58 Å2
Polarizability: 38.9±0.5 10-24cm3
Surface Tension: 39.5±3.0 dyne/cm
Molar Volume: 325.3±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) =  6.60

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  463.00  (Adapted Stein & Brown method)
    Melting Pt (deg C):  178.29  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.31E-011  (Modified Grain method)
    Subcooled liquid VP: 2.47E-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):  0.1721
       log Kow used: 6.60 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.51642 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 :   1.97E-009  atm-m3/mole
   Group Method:   8.10E-012  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.546E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.60  (KowWin est)
  Log Kaw used:  -7.094  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.694
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8264
   Biowin2 (Non-Linear Model)     :   0.5545
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0155  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9004  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6941
   Biowin6 (MITI Non-Linear Model):   0.5903
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8533
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  3.29E-007 Pa (2.47E-009 mm Hg)
  Log Koa (Koawin est  ): 13.694
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  9.11 
       Octanol/air (Koa) model:  12.1 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.997 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 241.8943 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 272.2943 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.531 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =   28.282 Min (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    52.000000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    80.000000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     0.529 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     0.344 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2215
      Log Koc:  3.345 

 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 = 1.750 (BCF = 56.23)
       log Kow used: 6.60 (estimated)

 Volatilization from Water:
    Henry LC:  8.1E-012 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 1.294E+008  hours   (5.392E+006 days)
    Half-Life from Model Lake : 1.412E+009  hours   (5.882E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              93.56  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    92.78  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       0.00998         0.353        1000       
   Water     4.59            360          1000       
   Soil      34.7            720          1000       
   Sediment  60.7            3.24e+003    0          
     Persistence Time: 1.24e+003 hr




                    

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