ChemSpider 2D Image | Harpagoside | C24H30O11

Harpagoside

  • Molecular FormulaC24H30O11
  • Average mass494.488 Da
  • Monoisotopic mass494.178802 Da
  • ChemSpider ID4444874
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 10 of 10 defined stereocentres


More details:






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

(1S,4aS,5R,7S,7aS)-1-(β-D-Glucopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl (2E)-3-phenylacrylate [ACD/IUPAC Name]
(1S,4aS,5R,7S,7aS)-1-(β-D-Glucopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl-(2E)-3-phenylacrylat [German] [ACD/IUPAC Name]
(2E)-3-Phénylacrylate de (1S,4aS,5R,7S,7aS)-1-(β-D-glucopyranosyloxy)-4a,5-dihydroxy-7-méthyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yle [French] [ACD/IUPAC Name]
2-Propenoic acid, 3-phenyl-, (1S,4aS,5R,7S,7aS)-1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methylcyclopenta[c]pyran-7-yl ester, (2E)- [ACD/Index Name]
Harpagoside
(1S-(1α,4aα,5α,7α(E),7aα))-1,4a,5,6,7,7a-Hexahydro-4a,5-dihydroxy-7-methyl-7-((allyl-1-oxo-3-phenyl)oxy)cyclopenta(c)pyran-1-yl-β-D-glucopyranoside
(1S,4aS,5R,7S,7aS)-1-(β-D-glucopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl (2E)-3-phenyl
(1S,4aS,5R,7S,7aS)-1-(β-D-glucopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl (2E)-3-phenylprop-2-enoate
(E)-3-phenylprop-2-enoic acid [(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] ester(E)-3-phenylacrylic acid [(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] ester
[(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

8KGS1DC5ZU [DBID]
C09783 [DBID]
UNII:8KGS1DC5ZU [DBID]
UNII-8KGS1DC5ZU [DBID]

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

Density: 1.5±0.1 g/cm3
Boiling Point: 720.7±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.4 mmHg at 25°C
Enthalpy of Vaporization: 110.5±3.0 kJ/mol
Flash Point: 244.3±26.4 °C
Index of Refraction: 1.660
Molar Refractivity: 119.9±0.4 cm3
#H bond acceptors: 11
#H bond donors: 6
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 2
ACD/LogP: -0.92
ACD/LogD (pH 5.5): -0.92
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 7.52
ACD/LogD (pH 7.4): -0.92
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 7.52
Polar Surface Area: 175 Å2
Polarizability: 47.5±0.5 10-24cm3
Surface Tension: 81.6±5.0 dyne/cm
Molar Volume: 324.9±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) =  -1.96

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  681.23  (Adapted Stein & Brown method)
    Melting Pt (deg C):  297.25  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.3E-020  (Modified Grain method)
    Subcooled liquid VP: 1.41E-017 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):  3.649e+004
       log Kow used: -1.96 (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
       Vinyl/Allyl Ethers
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.15E-022  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.318E-025 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.96  (KowWin est)
  Log Kaw used:  -20.328  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.368
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1981
   Biowin2 (Non-Linear Model)     :   0.0019
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6182  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6793  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7650
   Biowin6 (MITI Non-Linear Model):   0.0310
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1795
 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):  1.88E-015 Pa (1.41E-017 mm Hg)
  Log Koa (Koawin est  ): 18.368
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.6E+009 
       Octanol/air (Koa) model:  5.73E+005 
   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 = 194.4634 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 197.1234 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.660 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.651 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.925000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     2.975000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =    14.288 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     9.245 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   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    :  20.05
      Log Koc:  1.302 

 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: -1.96 (estimated)

 Volatilization from Water:
    Henry LC:  1.15E-022 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.132E+019  hours   (4.717E+017 days)
    Half-Life from Model Lake : 1.235E+020  hours   (5.146E+018 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       0.000226        1.21         1000       
   Water     46.5            900          1000       
   Soil      53.4            1.8e+003     1000       
   Sediment  0.0892          8.1e+003     0          
     Persistence Time: 971 hr




                    

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