ChemSpider 2D Image | Helenalin | C15H18O4

Helenalin

  • Molecular FormulaC15H18O4
  • Average mass262.301 Da
  • Monoisotopic mass262.120514 Da
  • ChemSpider ID21713
  • defined stereocentres - 6 of 6 defined stereocentres


More details:



Featured data source



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

(3aS,4S,4aR,7aR,8R,9aR)-4-Hydroxy-4a,8-dimethyl-3-methylen-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dion [German] [ACD/IUPAC Name]
(3aS,4S,4aR,7aR,8R,9aR)-4-Hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione [ACD/IUPAC Name]
(3aS,4S,4aR,7aR,8R,9aR)-4-Hydroxy-4a,8-diméthyl-3-méthylène-3,3a,4,4a,7a,8,9,9a-octahydroazuléno[6,5-b]furane-2,5-dione [French] [ACD/IUPAC Name]
(3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
[3aS-(3aa,4a,4ab,7aa,8a,9aa)]-3,3a,4,4a,7a,8,9,9a-Octahydro-4-hydroxy-4a,8-dimethyl-3-methyleneazuleno[6,5-b]furan-2,5-dione
4GUY9L896T
6754-13-8 [RN]
6a,8b-Dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic Acid 12,8-Lactone
Azuleno[6,5-b]furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS,4S,4aR,7aR,8R,9aR)- [ACD/Index Name]
Helenalin [Wiki]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS125803 [DBID]
AIDS-125803 [DBID]
BRN 0028081 [DBID]
C09473 [DBID]
HSDB 3490 [DBID]
nchembio.2007.59-comp17 [DBID]
NCI60_041870 [DBID]
NSC 85236 [DBID]
NSC85236 [DBID]
PF 56 [DBID]
  • Miscellaneous
    • Chemical Class:

      A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-<ital>b</ital>]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylid ene group at position 3 (the 3a<stereo>S</stereo>,4<stereo>S</stereo>,4a<stereo>R</stereo>,7a<stereo>R</stereo>,8<stereo>R</stereo>,9a<stereo>R</stereo> stereoisomer). ChEBI CHEBI:5635

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

Density: 1.3±0.1 g/cm3
Boiling Point: 473.0±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 84.9±6.0 kJ/mol
Flash Point: 179.9±22.2 °C
Index of Refraction: 1.565
Molar Refractivity: 68.2±0.4 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 0.70
ACD/LogD (pH 5.5): 0.78
ACD/BCF (pH 5.5): 2.29
ACD/KOC (pH 5.5): 63.00
ACD/LogD (pH 7.4): 0.78
ACD/BCF (pH 7.4): 2.29
ACD/KOC (pH 7.4): 63.00
Polar Surface Area: 64 Å2
Polarizability: 27.0±0.5 10-24cm3
Surface Tension: 47.4±5.0 dyne/cm
Molar Volume: 209.3±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) =  0.19
    Log Kow (Exper. database match) =  0.36
       Exper. Ref:  Hansch,C et al. (1995)
    Log Kow (Exper. database match) =  0.87
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  410.34  (Adapted Stein & Brown method)
    Melting Pt (deg C):  151.81  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.16E-009  (Modified Grain method)
    MP  (exp database):  167-168 deg C
    Subcooled liquid VP: 9.19E-008 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):  1.181e+004
       log Kow used: 0.87 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  154.65 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.38E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.235E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.87  (exp database)
  Log Kaw used:  -10.249  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.119
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7785
   Biowin2 (Non-Linear Model)     :   0.9093
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6851  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6520  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7295
   Biowin6 (MITI Non-Linear Model):   0.3493
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0386
 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):  1.23E-005 Pa (9.19E-008 mm Hg)
  Log Koa (Koawin est  ): 11.119
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.245 
       Octanol/air (Koa) model:  0.0323 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.898 
       Mackay model           :  0.951 
       Octanol/air (Koa) model:  0.721 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 117.3472 E-12 cm3/molecule-sec
      Half-Life =     0.091 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.094 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     2.275000 E-17 cm3/molecule-sec
      Half-Life =     0.504 Days (at 7E11 mol/cm3)
      Half-Life =     12.090 Hrs
   Fraction sorbed to airborne particulates (phi): 0.925 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  18.34
      Log Koc:  1.263 

 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: 0.87 (expkow database)

 Volatilization from Water:
    Henry LC:  1.38E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.871E+008  hours   (2.863E+007 days)
    Half-Life from Model Lake : 7.496E+009  hours   (3.123E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               1.88  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.78  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       0.000306        1.85         1000       
   Water     42              900          1000       
   Soil      57.9            1.8e+003     1000       
   Sediment  0.0865          8.1e+003     0          
     Persistence Time: 1.03e+003 hr




                    

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