ChemSpider 2D Image | Trilobatin | C21H24O10

Trilobatin

  • Molecular FormulaC21H24O10
  • Average mass436.409 Da
  • Monoisotopic mass436.136932 Da
  • ChemSpider ID4954251

  • defined stereocentres - 5 of 5 defined stereocentres

More details:

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

1-(2,6-DIHYDROXY-4-{[(2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}PHENYL)-3-(4-HYDROXYPHENYL)PROPAN-1-ONE
1-(4-(β-D-Glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-propanone
1-[2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
1-Propanone, 1-(4-(β-D-glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-
1-Propanone, 1-[4-(β-D-glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)- [ACD/Index Name]
3,5-Dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl β-D-glucopyranoside [ACD/IUPAC Name]
3,5-Dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl-β-D-glucopyranosid [German] [ACD/IUPAC Name]
4192-90-9 [RN]
p-Phloridzin
p-Phlorizin
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

23298I791N [DBID]
UNII:23298I791N [DBID]
UNII-23298I791N [DBID]
  • Miscellaneous

    • Chemical Class:

      An aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 4' via a glycosidic linkage. It is isolated from the leaves of the Chinese sweet tea Lithocarpus poly stachyus and exhibits significant anti-hyperglycemic, anti-oxidative and anti-inflammatory properties. ChEBI CHEBI:145829

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

Density: 1.6±0.1 g/cm3
Boiling Point: 787.9±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.9 mmHg at 25°C
Enthalpy of Vaporization: 120.2±3.0 kJ/mol
Flash Point: 277.1±26.4 °C
Index of Refraction: 1.686
Molar Refractivity: 106.8±0.3 cm3
#H bond acceptors: 10
#H bond donors: 7
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 2
ACD/LogP: 1.43
ACD/LogD (pH 5.5): 0.98
ACD/BCF (pH 5.5): 3.22
ACD/KOC (pH 5.5): 79.45
ACD/LogD (pH 7.4): 0.29
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 16.40
Polar Surface Area: 177 Å2
Polarizability: 42.3±0.5 10-24cm3
Surface Tension: 80.1±3.0 dyne/cm
Molar Volume: 280.5±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) =  1.50

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  683.32  (Adapted Stein & Brown method)
    Melting Pt (deg C):  298.23  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.07E-020  (Modified Grain method)
    Subcooled liquid VP: 1.19E-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):  364.1
       log Kow used: 1.50 (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 :   4.01E-025  atm-m3/mole
   Group Method:   2.18E-039  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.688E-023 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.50  (KowWin est)
  Log Kaw used:  -22.785  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  24.285
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.3682
   Biowin2 (Non-Linear Model)     :   0.9503
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8796  (weeks       )
   Biowin4 (Primary Survey Model) :   3.8316  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7201
   Biowin6 (MITI Non-Linear Model):   0.1500
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6930
 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):  1.59E-015 Pa (1.19E-017 mm Hg)
  Log Koa (Koawin est  ): 24.285
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.89E+009 
       Octanol/air (Koa) model:  4.73E+011 
   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 = 266.9600 E-12 cm3/molecule-sec
      Half-Life =     0.040 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    28.847 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    :  177.4
      Log Koc:  2.249 

 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 = -1.038 (BCF = 0.09159)
       log Kow used: 1.50 (estimated)

 Volatilization from Water:
    Henry LC:  4.01E-025 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  3.05E+021  hours   (1.271E+020 days)
    Half-Life from Model Lake : 3.327E+022  hours   (1.386E+021 days)

 Removal In Wastewater Treatment:
    Total removal:               1.97  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.88  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       1.4e-006        0.962        1000       
   Water     29.1            360          1000       
   Soil      70.8            720          1000       
   Sediment  0.0692          3.24e+003    0          
     Persistence Time: 652 hr

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