ChemSpider 2D Image | 1-O-(4-coumaroyl)-beta-D-glucose | C15H18O8


  • Molecular FormulaC15H18O8
  • Average mass326.299 Da
  • Monoisotopic mass326.100159 Da
  • ChemSpider ID10394547
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 5 defined stereocentres

More details:

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

1-O-[(2E)-3-(4-Hydroxyphenyl)-2-propenoyl]-β-D-glucopyranose [German] [ACD/IUPAC Name]
1-O-[(2E)-3-(4-Hydroxyphenyl)-2-propenoyl]-β-D-glucopyranose [ACD/IUPAC Name]
1-O-[(2E)-3-(4-Hydroxyphényl)-2-propenoyl]-β-D-glucopyranose [French] [ACD/IUPAC Name]
β-D-Glucopyranose, 1-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]- [ACD/Index Name]
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
  • Miscellaneous
    • Chemical Class:

      An <element>O</element>-acyl carbohydrate that is <stereo>beta</stereo>-<stereo>D</stereo>-glucose bearing a 4-coumaroyl substituent at position 1. ChEBI CHEBI:71498
      An O-acyl carbohydrate that is beta-D-glucose bearing a 4-coumaroyl substituent at position 1. ChEBI
    • Compound Source:

      2-O-acetyl-3-O-trans-coutarate biosynthesis PlantCyc CPD-8674
      acylated cyanidin galactoside biosynthesis PlantCyc CPD-8674
      Aegilops tauschii PlantCyc CPD-8674
      amaranthin biosynthesis PlantCyc CPD-8674
      Amaranthus hypochondriacus PlantCyc CPD-8674
      Amborella trichopoda PlantCyc CPD-8674
      Anacardium occidentale PlantCyc CPD-8674
      Asparagus officinalis PlantCyc CPD-8674
      Beta vulgaris subsp. vulgaris PlantCyc CPD-8674
      Brachypodium distachyon PlantCyc CPD-8674
      Calotropis gigantea PlantCyc CPD-8674
      Cannabis sativa PlantCyc CPD-8674
      Capsicum annuum PlantCyc CPD-8674
      Catharanthus roseus PlantCyc CPD-8674
      Chenopodium quinoa PlantCyc CPD-8674
      Cicer arietinum PlantCyc CPD-8674
      Citrus clementina PlantCyc CPD-8674
      Citrus sinensis PlantCyc CPD-8674
      Corchorus capsularis PlantCyc CPD-8674
      Cucumis sativus PlantCyc CPD-8674
      Daucus carota subsp. sativus PlantCyc CPD-8674
      Dianthus caryophyllus PlantCyc CPD-8674
      Eucalyptus grandis PlantCyc CPD-8674
      Fragaria vesca subsp. vesca PlantCyc CPD-8674
      Glycine max PlantCyc CPD-8674
      Gossypium raimondii PlantCyc CPD-8674
      Helianthus annuus PlantCyc CPD-8674
      Hordeum vulgare subsp. vulgare PlantCyc CPD-8674
      Humulus lupulus var. lupulus PlantCyc CPD-8674
      Kalanchoe fedtschenkoi PlantCyc CPD-8674
      Kalanchoe laxiflora PlantCyc CPD-8674
      lampranthin biosynthesis PlantCyc CPD-8674
      Leersia perrieri PlantCyc CPD-8674
      Linum usitatissimum PlantCyc CPD-8674
      Lotus japonicus PlantCyc CPD-8674
      Malus domestica PlantCyc CPD-8674
      Manihot esculenta PlantCyc CPD-8674
      Medicago truncatula PlantCyc CPD-8674
      Miscanthus sinensis PlantCyc CPD-8674
      Nicotiana tabacum PlantCyc CPD-8674
      Olea europaea var. sylvestris PlantCyc CPD-8674
      Oropetium thomaeum PlantCyc CPD-8674
      Oryza brachyantha PlantCyc CPD-8674
      Oryza glaberrima PlantCyc CPD-8674
      Oryza punctata PlantCyc CPD-8674
      Oryza rufipogon PlantCyc CPD-8674
      Oryza sativa Japonica Group PlantCyc CPD-8674
      Panicum hallii PlantCyc CPD-8674
      Panicum virgatum PlantCyc CPD-8674
      Petunia axillaris PlantCyc CPD-8674
      Phaseolus vulgaris PlantCyc CPD-8674
      Populus trichocarpa PlantCyc CPD-8674
      Prunus persica PlantCyc CPD-8674
      Ricinus communis PlantCyc CPD-8674
      Rosa chinensis PlantCyc CPD-8674
      Rosa multiflora PlantCyc CPD-8674
      Setaria italica PlantCyc CPD-8674
      Setaria viridis PlantCyc CPD-8674
      Solanum lycopersicum PlantCyc CPD-8674
      Solanum melongena PlantCyc CPD-8674
      Solanum pennellii PlantCyc CPD-8674
      Solanum tuberosum PlantCyc CPD-8674
      Sorghum bicolor PlantCyc CPD-8674
      Spinacia oleracea PlantCyc CPD-8674
      Spirodela polyrhiza PlantCyc CPD-8674
      ternatin C3 biosynthesis PlantCyc CPD-8674
      Theobroma cacao PlantCyc CPD-8674
      Trifolium pratense PlantCyc CPD-8674
      Triticum aestivum PlantCyc CPD-8674
      Triticum urartu PlantCyc CPD-8674
      Vitis vinifera PlantCyc CPD-8674
      Zea mays subsp. mays PlantCyc CPD-8674
    • Bio Activity:

      1-O-(4-coumaroyl)-beta-D-glucose + betanin + betanin + 1-O-(4-coumaroyl)-beta-D-glucose + H+ + H+ -> lampranthin I + D-glucopyranose PlantCyc CPD-8674
      1-O-(4-coumaroyl)-beta-D-glucose + meso-tartrate -> trans-coutarate + D-glucopyranose PlantCyc CPD-8674
      1-O-(4-coumaroyl)-beta-D-glucose + ternatin C5 + ternatin C5 + 1-O-(4-coumaroyl)-beta-D-glucose -> ternatin C3 + D-glucopyranose PlantCyc CPD-8674
      amaranthin + 1-O-(4-coumaroyl)-beta-D-glucose -> celosianin I + D-glucopyranose PlantCyc CPD-8674
      cyanidin 3-O-(6-O-beta-D-glucosyl-2-O-beta-D-xylosyl-beta-D-galactoside) + 1-O-(4-coumaroyl)-beta-D-glucose -> cyanidin O-O-[6-O-(6-O-4-hydroxycinnamoyl-beta-D-glucosyl)-2-O-beta-D-xylosyl-beta-D-galactoside] + D-glucopyranose + H+ PlantCyc CPD-8674
      ternatin C5 + 1-O-(4-coumaroyl)-beta-D-glucose -> ternatin C3 + D-glucopyranose PlantCyc CPD-8674

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

Density: 1.5±0.1 g/cm3
Boiling Point: 592.0±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 92.9±3.0 kJ/mol
Flash Point: 221.0±23.6 °C
Index of Refraction: 1.653
Molar Refractivity: 77.5±0.4 cm3
#H bond acceptors: 8
#H bond donors: 5
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: 1.04
ACD/LogD (pH 5.5): -0.26
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 17.27
ACD/LogD (pH 7.4): -0.26
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 17.17
Polar Surface Area: 137 Å2
Polarizability: 30.7±0.5 10-24cm3
Surface Tension: 84.6±5.0 dyne/cm
Molar Volume: 211.4±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) =  -1.20

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  524.52  (Adapted Stein & Brown method)
    Melting Pt (deg C):  224.05  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.21E-014  (Modified Grain method)
    Subcooled liquid VP: 2.99E-012 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):  3.443e+005
       log Kow used: -1.20 (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:

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.55E-021  atm-m3/mole
   Group Method:   4.45E-031  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  2.756E-020 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.20  (KowWin est)
  Log Kaw used:  -19.198  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.998
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1698
   Biowin2 (Non-Linear Model)     :   0.9879
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.3059  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.1537  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.9523
   Biowin6 (MITI Non-Linear Model):   0.5670
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.0569
 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):  3.99E-010 Pa (2.99E-012 mm Hg)
  Log Koa (Koawin est  ): 17.998
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.53E+003 
       Octanol/air (Koa) model:  2.44E+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 = 127.8045 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 130.4645 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.004 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.984 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.050000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     2.100000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     1.091 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =    13.097 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   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    :  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 :  1.012E-001  L/mol-sec
  Kb Half-Life at pH 8:      79.283  days   
  Kb Half-Life at pH 7:       2.171  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -1.20 (estimated)

 Volatilization from Water:
    Henry LC:  1.55E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.823E+017  hours   (2.843E+016 days)
    Half-Life from Model Lake : 7.444E+018  hours   (3.102E+017 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       2.39e-008       1.87         1000       
   Water     34.4            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