ChemSpider 2D Image | 4-coumaroylshikimic acid | C16H16O7

4-coumaroylshikimic acid

  • Molecular FormulaC16H16O7
  • Average mass320.294 Da
  • Monoisotopic mass320.089600 Da
  • ChemSpider ID4444183

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 3 of 3 defined stereocentres

More details:

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

(3R,4R,5R)-3,4-Dihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]oxy}-1-cyclohexen-1-carbonsäure [German] [ACD/IUPAC Name]
(3R,4R,5R)-3,4-Dihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]oxy}-1-cyclohexene-1-carboxylic acid [ACD/IUPAC Name]
1-Cyclohexene-1-carboxylic acid, 3,4-dihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-, (3R,4R,5R)- [ACD/Index Name]
4-coumaroylshikimic acid
Acide (3R,4R,5R)-3,4-dihydroxy-5-{[(2E)-3-(4-hydroxyphényl)-2-propenoyl]oxy}-1-cyclohexène-1-carboxylique [French] [ACD/IUPAC Name]
(3{r},4{r},5{r})-5-[({e})-3-(4-Hydroxyphenyl)prop-2-Enoyl]oxy-3,4-Bis(Oxidanyl)cyclohexene-1-Carboxylic Acid
(3R,4R,5R)-3,4-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyloxy]cyclohex-1-ene-1-carboxylic acid
4-coumaroylshikimate
SKT
trans-5-O-(4-coumaroyl)shikimate

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

C02947 [DBID]
CHEBI:16428 [DBID]

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

Density: 1.5±0.1 g/cm3
Boiling Point: 582.8±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 91.6±3.0 kJ/mol
Flash Point: 217.5±23.6 °C
Index of Refraction: 1.660
Molar Refractivity: 78.6±0.4 cm3
#H bond acceptors: 7
#H bond donors: 4
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 1.10
ACD/LogD (pH 5.5): -0.46
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 3.40
ACD/LogD (pH 7.4): -2.24
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 124 Å2
Polarizability: 31.2±0.5 10-24cm3
Surface Tension: 79.9±5.0 dyne/cm
Molar Volume: 213.1±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) =  0.57

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  516.32  (Adapted Stein & Brown method)
    Melting Pt (deg C):  220.22  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.49E-013  (Modified Grain method)
    Subcooled liquid VP: 1.82E-011 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):  2.861e+004
       log Kow used: 0.57 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  7.1989e+005 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylates-acid
       Phenols-acid
       Vinyl/Allyl Alcohols-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.31E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.195E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.57  (KowWin est)
  Log Kaw used:  -18.754  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.324
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2752
   Biowin2 (Non-Linear Model)     :   0.9982
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.3725  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.2987  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7791
   Biowin6 (MITI Non-Linear Model):   0.4429
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.9370
 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-009 Pa (1.82E-011 mm Hg)
  Log Koa (Koawin est  ): 19.324
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.24E+003 
       Octanol/air (Koa) model:  5.18E+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 = 106.8970 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 109.5570 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.201 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.172 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     8.443749 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     9.493750 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     3.257 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     2.897 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 :  8.515E-003  L/mol-sec
  Kb Half-Life at pH 8:       2.579  years  
  Kb Half-Life at pH 7:      25.792  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 0.57 (estimated)

 Volatilization from Water:
    Henry LC:  4.31E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.431E+017  hours   (1.013E+016 days)
    Half-Life from Model Lake : 2.652E+018  hours   (1.105E+017 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       1.06e-008       1.38         1000       
   Water     33              208          1000       
   Soil      66.9            416          1000       
   Sediment  0.059           1.87e+003    0          
     Persistence Time: 393 hr

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