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ChemSpider 2D Image | luzonidial B | C19H18O6

luzonidial B

  • Molecular FormulaC19H18O6
  • Average mass342.343 Da
  • Monoisotopic mass342.110352 Da
  • ChemSpider ID7827834
  • 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,4R)-3-Formyl-2-(hydroxymethyl)-4-(3-oxo-1-propen-2-yl)-2-cyclopenten-1-yl (2Z)-3-(4-hydroxyphenyl)acrylate [ACD/IUPAC Name]
(1S,4R)-3-Formyl-2-(hydroxymethyl)-4-(3-oxo-1-propen-2-yl)-2-cyclopenten-1-yl-(2Z)-3-(4-hydroxyphenyl)acrylat [German] [ACD/IUPAC Name]
(2Z)-3-(4-Hydroxyphényl)acrylate de (1S,4R)-3-formyl-2-(hydroxyméthyl)-4-(3-oxo-1-propén-2-yl)-2-cyclopentén-1-yle [French] [ACD/IUPAC Name]
2-Propenoic acid, 3-(4-hydroxyphenyl)-, (1S,4R)-3-formyl-4-(1-formylethenyl)-2-(hydroxymethyl)-2-cyclopenten-1-yl ester, (2Z)- [ACD/Index Name]
luzonidial B
(1S,4R)-3-formyl-2-(hydroxymethyl)-4-(3-oxoprop-1-en-2-yl)cyclopent-2-en-1-yl (2Z)-3-(4-hydroxyphenyl)prop-2-enoate
  • Miscellaneous
    • Chemical Class:

      An iridoid monoterpenoid that is cyclopentene substituted by a formyl group at position 3, a hydroxymethyl group at position 2, 3-oxopropen-2yl group at position 4 and a <stereo>cis</stereo>-4-coumaro yloxy moiety at position 1 (the 1<stereo>S</stereo>,4<stereo>R</stereo> stereoisomer). Isolated from the leaves of <ital>Viburnum luzonicum</ital>, it exhibits antineoplastic activity. ChEBI CHEBI:66600
      An iridoid monoterpenoid that is cyclopentene substituted by a formyl group at position 3, a hydroxymethyl group at position 2, 3-oxopropen-2yl group at position 4 and a cis-4-coumaro; yloxy moiety at position 1 (the 1S,4R stereoisomer). Isolated from the leaves of Viburnum luzonicum, it exhibits antineoplastic activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:66600

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

Density: 1.3±0.1 g/cm3
Boiling Point: 589.7±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 92.6±3.0 kJ/mol
Flash Point: 213.7±23.6 °C
Index of Refraction: 1.608
Molar Refractivity: 89.4±0.4 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 1.47
ACD/LogD (pH 5.5): 1.59
ACD/BCF (pH 5.5): 9.52
ACD/KOC (pH 5.5): 174.66
ACD/LogD (pH 7.4): 1.59
ACD/BCF (pH 7.4): 9.47
ACD/KOC (pH 7.4): 173.76
Polar Surface Area: 101 Å2
Polarizability: 35.4±0.5 10-24cm3
Surface Tension: 60.0±5.0 dyne/cm
Molar Volume: 258.5±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) =  1.41

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  500.45  (Adapted Stein & Brown method)
    Melting Pt (deg C):  212.81  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.82E-012  (Modified Grain method)
    Subcooled liquid VP: 1.81E-010 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):  5290
       log Kow used: 1.41 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3.6496e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.31E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.550E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.41  (KowWin est)
  Log Kaw used:  -18.271  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.681
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.6025
   Biowin2 (Non-Linear Model)     :   1.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8438  (weeks       )
   Biowin4 (Primary Survey Model) :   4.1452  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   1.2372
   Biowin6 (MITI Non-Linear Model):   0.9556
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7756
 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):  2.41E-008 Pa (1.81E-010 mm Hg)
  Log Koa (Koawin est  ): 19.681
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  124 
       Octanol/air (Koa) model:  1.18E+007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 148.1288 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 150.7888 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.866 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.851 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     8.921500 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     9.971500 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     3.083 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     2.758 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Reaction With Nitrate Radicals May Be Important!
   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    :  59.23
      Log Koc:  1.773 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.877E-003  L/mol-sec
  Kb Half-Life at pH 8:       7.633  years  
  Kb Half-Life at pH 7:      76.329  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = -0.264 (BCF = 0.5448)
       log Kow used: 1.41 (estimated)

 Volatilization from Water:
    Henry LC:  1.31E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.269E+016  hours   (3.446E+015 days)
    Half-Life from Model Lake : 9.021E+017  hours   (3.759E+016 days)

 Removal In Wastewater Treatment:
    Total removal:               1.95  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.86  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       1.91e-009       1.11         1000       
   Water     30.3            360          1000       
   Soil      69.7            720          1000       
   Sediment  0.0688          3.24e+003    0          
     Persistence Time: 643 hr




                    

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