ChemSpider 2D Image | luzonial B | C19H20O7

luzonial B

  • Molecular FormulaC19H20O7
  • Average mass360.358 Da
  • Monoisotopic mass360.120911 Da
  • ChemSpider ID7827833

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 5 defined stereocentres

More details:

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

(1S,3aS,4S,6S,6aS)-1,3a-Dihydroxy-6-(3-oxo-1-propen-2-yl)hexahydro-1H-cyclopenta[c]furan-4-yl (2Z)-3-(4-hydroxyphenyl)acrylate [ACD/IUPAC Name]
(1S,3aS,4S,6S,6aS)-1,3a-Dihydroxy-6-(3-oxo-1-propen-2-yl)hexahydro-1H-cyclopenta[c]furan-4-yl-(2Z)-3-(4-hydroxyphenyl)acrylat [German] [ACD/IUPAC Name]
(2Z)-3-(4-Hydroxyphényl)acrylate de (1S,3aS,4S,6S,6aS)-1,3a-dihydroxy-6-(3-oxo-1-propén-2-yl)hexahydro-1H-cyclopenta[c]furan-4-yle [French] [ACD/IUPAC Name]
2-Propenoic acid, 3-(4-hydroxyphenyl)-, (1S,3aS,4S,6S,6aS)-6-(1-formylethenyl)hexahydro-1,3a-dihydroxy-1H-cyclopenta[c]furan-4-yl ester, (2Z)- [ACD/Index Name]
luzonial B
(1S,3aS,4S,6S,6aS)-1,3a-dihydroxy-6-(3-oxoprop-1-en-2-yl)hexahydro-1H-cyclopenta[c]furan-4-yl (2Z)-3-(4-hydroxyphenyl)prop-2-enoate
  • Miscellaneous

    • Chemical Class:

      An iridoid monoterpenoid that is hexahydro-1<element>H</element>-cyclopenta[<ital>c</ital>]furan substituted by hydroxy groups at positions 1 and 3a, a 3-oxopropen-2yl group at position 6 and a <stere o>cis</stereo>-4-coumaroyloxy moiety at position 4 (the 1<stereo>S</stereo>,3a<stereo>S</stereo>,4<stereo>S</stereo>,6<stereo>S</stereo>,6a<stereo>S</stereo> stereoisomer). Isolated from the leaves of <ital>Viburnum luzonicum</ital>, it exhibits antineoplastic activity. ChEBI CHEBI:66599
      An iridoid monoterpenoid that is hexahydro-1H-cyclopenta[c]furan substituted by hydroxy groups at positions 1 and 3a, a 3-oxopropen-2yl group at position 6 and a cis-4-coumaroyloxy moiety at position 4 (the 1S,3aS,4S,6S,6aS stereoisomer). Isolated from the leaves of Viburnum luzonicum, it exhibits antineoplastic activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:66599, CHEBI:66599

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

Density: 1.4±0.1 g/cm3
Boiling Point: 619.1±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 96.5±3.0 kJ/mol
Flash Point: 224.3±25.0 °C
Index of Refraction: 1.631
Molar Refractivity: 90.8±0.4 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 0.80
ACD/LogD (pH 5.5): 0.85
ACD/BCF (pH 5.5): 2.58
ACD/KOC (pH 5.5): 68.62
ACD/LogD (pH 7.4): 0.84
ACD/BCF (pH 7.4): 2.57
ACD/KOC (pH 7.4): 68.26
Polar Surface Area: 113 Å2
Polarizability: 36.0±0.5 10-24cm3
Surface Tension: 67.7±5.0 dyne/cm
Molar Volume: 254.7±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) =  -0.02

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  505.90  (Adapted Stein & Brown method)
    Melting Pt (deg C):  215.35  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.66E-013  (Modified Grain method)
    Subcooled liquid VP: 3.9E-011 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):  2.14e+004
       log Kow used: -0.02 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylates
       Aldehydes
       Phenols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.18E-022  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.110E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.02  (KowWin est)
  Log Kaw used:  -19.674  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.654
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7780
   Biowin2 (Non-Linear Model)     :   0.9976
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5609  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7594  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8365
   Biowin6 (MITI Non-Linear Model):   0.4125
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0055
 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):  5.2E-009 Pa (3.9E-011 mm Hg)
  Log Koa (Koawin est  ): 19.654
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  577 
       Octanol/air (Koa) model:  1.11E+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 = 148.9442 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 151.6042 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.862 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.847 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.232000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     2.282000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =    22.325 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =    12.053 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    :  10
      Log Koc:  1.000 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  8.952E-003  L/mol-sec
  Kb Half-Life at pH 8:       2.454  years  
  Kb Half-Life at pH 7:      24.535  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -0.02 (estimated)

 Volatilization from Water:
    Henry LC:  5.18E-022 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.146E+018  hours   (8.94E+016 days)
    Half-Life from Model Lake : 2.341E+019  hours   (9.753E+017 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       2.32e-010       1.6          1000       
   Water     45.8            900          1000       
   Soil      54.1            1.8e+003     1000       
   Sediment  0.0887          8.1e+003     0          
     Persistence Time: 981 hr

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