ChemSpider 2D Image | Secoxyloganin | C17H24O11

Secoxyloganin

  • Molecular FormulaC17H24O11
  • Average mass404.366 Da
  • Monoisotopic mass404.131866 Da
  • ChemSpider ID142980

  • defined stereocentres - 8 of 8 defined stereocentres

More details:

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

[(2S,3R,4S)-2-(β-D-Glucopyranosyloxy)-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]acetic acid [ACD/IUPAC Name]
[(2S,3R,4S)-2-(β-D-Glucopyranosyloxy)-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]essigsäure [German] [ACD/IUPAC Name]
2H-Pyran-4-acetic acid, 3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, (2S,3R,4S)- [ACD/Index Name]
58822-47-2 [RN]
Acide [(2S,3R,4S)-2-(β-D-glucopyranosyloxy)-5-(méthoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]acétique [French] [ACD/IUPAC Name]
Secoxyloganin
(2S-(2α,3β,4β))-3-Ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetic acid
(2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetic acid
[(2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-5-(methoxycarbonyl)-3,4-dihydro-2H-pyran-4-yl]acetic acid
[(2S,3R,4S)-3-ETHENYL-5-(METHOXYCARBONYL)-2-{[(2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}-3,4-DIHYDRO-2H-PYRAN-4-YL]ACETIC ACID
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  • Miscellaneous

    • Chemical Class:

      A secoiridoid glycoside that is [(2<stereo>R</stereo>,3<stereo>R</stereo>,4<stereo>S</stereo>)-2-hydroxy-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2<element>H</element>-pyran-4-yl]acetic acid in which t he anometric hydroxy group has been converted to the corresponding <stereo>beta</stereo>-<stereo>D</stereo>-glucoside. It has been isolated from several plant species and exhibits antioxidant and anti -allergic properties. ChEBI CHEBI:132712
      A secoiridoid glycoside that is [(2R,3R,4S)-2-hydroxy-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]acetic acid in which t; he anometric hydroxy group has been converted to the corresponding b eta-D-glucoside. It has been isolated from several plant species and exhibits antioxidant and anti; -allergic properties. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:132712
      A secoiridoid glycoside that is [(2R,3R,4S)-2-hydroxy-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]acetic acid in which the anometric hydroxy group has been converted to the corresponding bet a-D-glucoside. It has been isolated from several plant species and exhibits antioxidant and anti-allergic properties. ChEBI CHEBI:132712

    • Compound Source:

      Calycophyllum spruceanum (Rubiaceae) Susan Richardson [Structure found in ChemSpider, confirmed from DOI: 10.1039/C3AY41476K]
      Isolated from a plant Susan Richardson [Structure found in ChemSpider, confirmed from DOI: 10.1039/C3AY41476K]

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

Density: 1.5±0.1 g/cm3
Boiling Point: 649.5±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.4 mmHg at 25°C
Enthalpy of Vaporization: 109.6±6.0 kJ/mol
Flash Point: 231.8±25.0 °C
Index of Refraction: 1.589
Molar Refractivity: 90.8±0.4 cm3
#H bond acceptors: 11
#H bond donors: 5
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 2
ACD/LogP: -2.02
ACD/LogD (pH 5.5): -3.02
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.82
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 172 Å2
Polarizability: 36.0±0.5 10-24cm3
Surface Tension: 72.1±5.0 dyne/cm
Molar Volume: 269.6±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) =  -1.65

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  590.52  (Adapted Stein & Brown method)
    Melting Pt (deg C):  254.88  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.69E-017  (Modified Grain method)
    Subcooled liquid VP: 1.82E-014 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):  1.841e+005
       log Kow used: -1.65 (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-acid
       Vinyl/Allyl Ethers-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.16E-023  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.644E-022 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.65  (KowWin est)
  Log Kaw used:  -21.054  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.404
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3947
   Biowin2 (Non-Linear Model)     :   0.0213
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.4242  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.3674  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.9065
   Biowin6 (MITI Non-Linear Model):   0.1284
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.9479
 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):  2.43E-012 Pa (1.82E-014 mm Hg)
  Log Koa (Koawin est  ): 19.404
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.24E+006 
       Octanol/air (Koa) model:  6.22E+006 
   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 = 144.0780 E-12 cm3/molecule-sec
      Half-Life =     0.074 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.891 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     6.887500 E-17 cm3/molecule-sec
      Half-Life =     0.166 Days (at 7E11 mol/cm3)
      Half-Life =      3.993 Hrs
   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 :  2.069E-003  L/mol-sec
  Kb Half-Life at pH 8:      10.614  years  
  Kb Half-Life at pH 7:     106.143  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -1.65 (estimated)

 Volatilization from Water:
    Henry LC:  2.16E-023 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.451E+019  hours   (2.271E+018 days)
    Half-Life from Model Lake : 5.946E+020  hours   (2.478E+019 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       6.41e-008       1.23         1000       
   Water     34.5            208          1000       
   Soil      65.5            416          1000       
   Sediment  0.0596          1.87e+003    0          
     Persistence Time: 387 hr

Click to predict properties on the Chemicalize site


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