ChemSpider 2D Image | Plantagoside | C21H22O12

Plantagoside

  • Molecular FormulaC21H22O12
  • Average mass466.392 Da
  • Monoisotopic mass466.111115 Da
  • ChemSpider ID151954

  • defined stereocentres - 6 of 6 defined stereocentres

More details:

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

(2S)-2-(3,4-dihydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one
(2S)-2-[3-(β-D-Glucopyranosyloxy)-4,5-dihydroxyphenyl]-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2-(3-(β-D-glucopyranosyloxy)-4,5-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (S)-
4H-1-Benzopyran-4-one, 2-[3-(β-D-glucopyranosyloxy)-4,5-dihydroxyphenyl]-2,3-dihydro-5,7-dihydroxy-, (2S)- [ACD/Index Name]
5-[(2S)-5,7-Dihydroxy-4-oxo-3,4-dihydro-2H-chromen-2-yl]-2,3-dihydroxyphenyl β-D-glucopyranoside [ACD/IUPAC Name]
5-[(2S)-5,7-Dihydroxy-4-oxo-3,4-dihydro-2H-chromen-2-yl]-2,3-dihydroxyphenyl-β-D-glucopyranosid [German] [ACD/IUPAC Name]
78708-33-5 [RN]
Plantagoside
β-D-Glucopyranoside de 5-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chromén-2-yl]-2,3-dihydroxyphényle [French] [ACD/IUPAC Name]
(2S)-2-(3,4-DIHYDROXY-5-{[(2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}PHENYL)-5,7-DIHYDROXY-2,3-DIHYDRO-1-BENZOPYRAN-4-ONE
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

FR4TR9587N [DBID]
UNII:FR4TR9587N [DBID]
UNII-FR4TR9587N [DBID]
  • Miscellaneous

    • Chemical Class:

      A flavanone glycoside that is (2<stereo>S</stereo>)-flavanone substituted by hydroxy groups at positions 5, 7, 4' and 5' and a <stereo>beta</stereo>-<stereo>D</stereo>-glucopyranosyloxy group at posi tion 3' respectively. ChEBI CHEBI:81163
      A flavanone glycoside that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 4' and 5' and a beta-D-glucopyranosyloxy group at posi; tion 3' respectively. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:81163
      A flavanone glycoside that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 4' and 5' and a beta-D-glucopyranosyloxy group at position 3' respectively. ChEBI CHEBI:81163

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

Density: 1.7±0.1 g/cm3
Boiling Point: 868.6±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.3 mmHg at 25°C
Enthalpy of Vaporization: 132.3±3.0 kJ/mol
Flash Point: 305.2±27.8 °C
Index of Refraction: 1.735
Molar Refractivity: 107.8±0.3 cm3
#H bond acceptors: 12
#H bond donors: 8
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 2
ACD/LogP: -0.33
ACD/LogD (pH 5.5): -0.21
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 18.22
ACD/LogD (pH 7.4): -0.65
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 6.55
Polar Surface Area: 207 Å2
Polarizability: 42.8±0.5 10-24cm3
Surface Tension: 104.0±3.0 dyne/cm
Molar Volume: 268.8±3.0 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) =  -0.61

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  745.99  (Adapted Stein & Brown method)
    Melting Pt (deg C):  327.50  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.9E-023  (Modified Grain method)
    Subcooled liquid VP: 7.65E-020 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):  1.49e+004
       log Kow used: -0.61 (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:
       Phenols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.51E-034  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.194E-027 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.61  (KowWin est)
  Log Kaw used:  -31.575  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  30.965
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.5470
   Biowin2 (Non-Linear Model)     :   0.9940
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8865  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9737  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8902
   Biowin6 (MITI Non-Linear Model):   0.3026
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.1515
 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):  1.02E-017 Pa (7.65E-020 mm Hg)
  Log Koa (Koawin est  ): 30.965
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.94E+011 
       Octanol/air (Koa) model:  2.26E+018 
   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 = 309.6100 E-12 cm3/molecule-sec
      Half-Life =     0.035 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    24.874 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  120.5
      Log Koc:  2.081 

 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: -0.61 (estimated)

 Volatilization from Water:
    Henry LC:  6.51E-034 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.942E+030  hours   (8.093E+028 days)
    Half-Life from Model Lake : 2.119E+031  hours   (8.829E+029 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       4.85e-013       0.829        1000       
   Water     38.9            360          1000       
   Soil      61.1            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 580 hr

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