ChemSpider 2D Image | ll z1640-2 | C19H22O7

ll z1640-2

  • Molecular FormulaC19H22O7
  • Average mass362.374 Da
  • Monoisotopic mass362.136566 Da
  • ChemSpider ID7974826

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 3 of 3 defined stereocentres

More details:

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

(3S,5E,8S,9S,11E)-8,9,16-Trihydroxy-14-methoxy-3-methyl-3,4,9,10-tetrahydro-1H-2-benzoxacyclotetradecin-1,7(8H)-dion [German] [ACD/IUPAC Name]
(3S,5E,8S,9S,11E)-8,9,16-Trihydroxy-14-methoxy-3-methyl-3,4,9,10-tetrahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione [ACD/IUPAC Name]
(3S,5E,8S,9S,11E)-8,9,16-Trihydroxy-14-méthoxy-3-méthyl-3,4,9,10-tétrahydro-1H-2-benzoxacyclotétradécine-1,7(8H)-dione [French] [ACD/IUPAC Name]
(5E)-7-Oxozeaenol
1198574-97-8 [RN]
1H-2-Benzoxacyclotetradecin-1,7(8H)-dione, 3,4,9,10-tetrahydro-8,9,16-trihydroxy-14-methoxy-3-methyl-, (3S,5E,8S,9S,11E)- [ACD/Index Name]
5E-7-oxozeaenol
66018-38-0 [RN]
ll z1640-2
(2E,5S,6S,8E,11S)-5,6,15-trihydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(18),2,8,14,16-pentaene-7,13-dione
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A macrolide that is the 7-oxo derivative of zeaenol (the 5<stereo>E</stereo> stereoisomer). Isolated from <ital>Fungi</ital>, it exhibits cytotoxic, antibacterial and inhibitory activity against NF- <greek>kappa</greek>B. ChEBI CHEBI:67558
      A macrolide that is the 7-oxo derivative of zeaenol (the 5E stereoisomer). Isolated from Fungi, it exhibits cytotoxic, antibacterial and inhibitory activity against NF-kappaB. ChEBI CHEBI:67558

    • Bio Activity:

      Enzymes Tocris Bioscience 3604
      Kinases Tocris Bioscience 3604
      Other Kinases Tocris Bioscience 3604
      Potent and selective TAK1 MAPKKK inhibitor Tocris Bioscience 3604
      Resorcyclic lactone of fungal origin that acts as a potent and selective transforming growth factor-?-activated kinase 1 (TAK1) mitogen-activated protein kinase kinase kinase (MAPKKK) inhibitor (IC50 = 8 nM). Displays > 33-fold and > 62-fold selectivity over MEKK1 and MEKK4 respectively. Inhibits IL-1-induced activation of NF-?B (IC50 = 83 nM) and JNK/p38. Inhibits production of inflammatory media tors, and sensitizes cells to TRAIL- and TNF-?-induced apoptosis in vitro. Tocris Bioscience 3604
      Resorcyclic lactone of fungal origin that acts as a potent and selective transforming growth factor-?-activated kinase 1 (TAK1) mitogen-activated protein kinase kinase kinase (MAPKKK) inhibitor (IC50 = 8 nM). Displays > 33-fold and > 62-fold selectivity over MEKK1 and MEKK4 respectively. Inhibits IL-1-induced activation of NF-?B (IC50 = 83 nM) and JNK/p38. Inhibits production of inflammatory mediators, and sensitizes cells to TRAIL- and TNF-?-induced apoptosis in vitro. Tocris Bioscience 3604
      Resorcyclic lactone of fungal origin that acts as a potent and selective transforming growth factor-beta-activated kinase 1 (TAK1) mitogen-activated protein kinase kinase kinase (MAPKKK) inhibitor (IC50 = 8 nM). Displays > 33-fold and > 62-fold selectivity over MEKK1 and MEKK4 respectively. Inhibits IL-1-induced activation of NF-kappaB (IC50 = 83 nM) and JNK/p38. Inhibits production of inflammatory mediators, and sensitizes cells to TRAIL- and TNF-alpha-induced apoptosis in vitro. Tocris Bioscience 3604

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

Density: 1.3±0.1 g/cm3
Boiling Point: 666.8±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 103.0±3.0 kJ/mol
Flash Point: 240.2±25.0 °C
Index of Refraction: 1.565
Molar Refractivity: 92.8±0.3 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 1.96
ACD/LogD (pH 5.5): 2.11
ACD/BCF (pH 5.5): 23.43
ACD/KOC (pH 5.5): 331.36
ACD/LogD (pH 7.4): 1.77
ACD/BCF (pH 7.4): 10.83
ACD/KOC (pH 7.4): 153.13
Polar Surface Area: 113 Å2
Polarizability: 36.8±0.5 10-24cm3
Surface Tension: 50.6±3.0 dyne/cm
Molar Volume: 285.2±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) =  2.92

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  573.14  (Adapted Stein & Brown method)
    Melting Pt (deg C):  246.76  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.05E-015  (Modified Grain method)
    Subcooled liquid VP: 2.69E-013 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):  63.3
       log Kow used: 2.92 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  61.108 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Phenols
       Vinyl/Allyl Ketones
       Salicylates

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.07E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.909E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.92  (KowWin est)
  Log Kaw used:  -10.539  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.459
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.3212
   Biowin2 (Non-Linear Model)     :   0.9990
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8343  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9074  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7961
   Biowin6 (MITI Non-Linear Model):   0.4112
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3745
 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):  3.59E-011 Pa (2.69E-013 mm Hg)
  Log Koa (Koawin est  ): 13.459
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  8.36E+004 
       Octanol/air (Koa) model:  7.06 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.998 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 153.5278 E-12 cm3/molecule-sec
      Half-Life =     0.070 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.836 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    14.787499 E-17 cm3/molecule-sec
      Half-Life =     0.077 Days (at 7E11 mol/cm3)
      Half-Life =      1.860 Hrs
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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 = 1.550 (BCF = 35.5)
       log Kow used: 2.92 (estimated)

 Volatilization from Water:
    Henry LC:  7.07E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.576E+009  hours   (6.568E+007 days)
    Half-Life from Model Lake :  1.72E+010  hours   (7.166E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               5.06  percent
    Total biodegradation:        0.12  percent
    Total sludge adsorption:     4.95  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       0.0862          0.881        1000       
   Water     25.2            360          1000       
   Soil      74.3            720          1000       
   Sediment  0.364           3.24e+003    0          
     Persistence Time: 467 hr

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