ChemSpider 2D Image | lactucin | C15H16O5

lactucin

  • Molecular FormulaC15H16O5
  • Average mass276.284 Da
  • Monoisotopic mass276.099762 Da
  • ChemSpider ID390746

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(3aR,4S,9aS,9bR)-4-Hydroxy-9-(hydroxymethyl)-6-methyl-3-methylen-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dion [German] [ACD/IUPAC Name]
(3aR,4S,9aS,9bR)-4-Hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione [ACD/IUPAC Name]
(3aR,4S,9aS,9bR)-4-Hydroxy-9-(hydroxyméthyl)-6-méthyl-3-méthylène-3,3a,4,5,9a,9b-hexahydroazuléno[4,5-b]furane-2,7-dione [French] [ACD/IUPAC Name]
1891-29-8 [RN]
Azuleno[4,5-b]furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-, (3aR,4S,9aS,9bR)- [ACD/Index Name]
lactucin [Wiki]
R6E2918904
(3aR,4S,9aS,9bR)-4-hydroxy-6-methyl-3-methylene-9-methylol-4,5,9a,9b-tetrahydro-3aH-azuleno[5,4-d]furan-2,7-quinone
(3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-4,5,9a,9b-tetrahydro-3aH-azuleno[5,4-d]furan-2,7-dione
(3AR,4S,9AS,9BR)-4-HYDROXY-9-(HYDROXYMETHYL)-6-METHYL-3-METHYLIDENE-2H,3H,3AH,4H,5H,7H,9AH,9BH-AZULENO[4,5-B]FURAN-2,7-DIONE
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C09489 [DBID]
  • Miscellaneous

    • Chemical Class:

      An azulenofuran that is 3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-<ital>b</ital>]furan-2,7-dione carrying additional hydroxy, methyl and hydroxymethyl substituents at positions 4, 6 and 9 resp ectively (the 3a<stereo>R</stereo>,4<stereo>S</stereo>,9a<stereo>S</stereo>,9b<stereo>R</stereo>-diastereomer). Found in chicory. ChEBI CHEBI:6358
      An azulenofuran that is 3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione carrying additional hydroxy, methyl and hydroxymethyl substituents at positions 4, 6 and 9 resp; ectively (t he 3aR,4S,9aS,9bR-diastereomer). Found in chicory. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6358
      An azulenofuran that is 3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione carrying additional hydroxy, methyl and hydroxymethyl substituents at positions 4, 6 and 9 respectively (the 3aR,4S,9aS,9bR-diastereomer). Found in chicory. ChEBI CHEBI:6358

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

Density: 1.4±0.1 g/cm3
Boiling Point: 575.6±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.6 mmHg at 25°C
Enthalpy of Vaporization: 99.0±6.0 kJ/mol
Flash Point: 221.7±23.6 °C
Index of Refraction: 1.612
Molar Refractivity: 69.0±0.4 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 0.33
ACD/LogD (pH 5.5): 0.82
ACD/BCF (pH 5.5): 2.46
ACD/KOC (pH 5.5): 66.32
ACD/LogD (pH 7.4): 0.82
ACD/BCF (pH 7.4): 2.46
ACD/KOC (pH 7.4): 66.32
Polar Surface Area: 84 Å2
Polarizability: 27.4±0.5 10-24cm3
Surface Tension: 58.1±5.0 dyne/cm
Molar Volume: 198.6±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) =  -0.73

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  465.18  (Adapted Stein & Brown method)
    Melting Pt (deg C):  188.99  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.44E-011  (Modified Grain method)
    Subcooled liquid VP: 7.53E-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):  7.107e+004
       log Kow used: -0.73 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  9420.1 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.90E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.366E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.73  (KowWin est)
  Log Kaw used:  -11.797  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.067
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1145
   Biowin2 (Non-Linear Model)     :   0.9929
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0263  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9148  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8118
   Biowin6 (MITI Non-Linear Model):   0.5226
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6452
 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):  1E-007 Pa (7.53E-010 mm Hg)
  Log Koa (Koawin est  ): 11.067
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  29.9 
       Octanol/air (Koa) model:  0.0286 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.696 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 108.4225 E-12 cm3/molecule-sec
      Half-Life =     0.099 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.184 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    56.590622 E-17 cm3/molecule-sec
      Half-Life =     0.020 Days (at 7E11 mol/cm3)
      Half-Life =     29.161 Min
   Fraction sorbed to airborne particulates (phi): 0.999 (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 = 0.500 (BCF = 3.162)
       log Kow used: -0.73 (estimated)

 Volatilization from Water:
    Henry LC:  3.9E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.495E+010  hours   (1.04E+009 days)
    Half-Life from Model Lake : 2.722E+011  hours   (1.134E+010 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       0.00134         0.403        1000       
   Water     39.1            360          1000       
   Soil      60.8            720          1000       
   Sediment  0.0716          3.24e+003    0          
     Persistence Time: 571 hr

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