ChemSpider 2D Image | (-)-3-dehydroshikimic acid | C7H8O5

(-)-3-dehydroshikimic acid

  • Molecular FormulaC7H8O5
  • Average mass172.135 Da
  • Monoisotopic mass172.037170 Da
  • ChemSpider ID388830

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(-)-3-dehydroshikimic acid
(−)-3-DHS
(4S,5R)-(-)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid
(4S,5R)-4,5-Dihydroxy-3-oxo-1-cyclohexen-1-carbonsäure [German] [ACD/IUPAC Name]
(4S,5R)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid [ACD/IUPAC Name]
(4S,5R)-4,5-Dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid
1-Cyclohexene-1-carboxylic acid, 4,5-dihydroxy-3-oxo-, (4S,5R)- [ACD/Index Name]
2922-42-1 [RN]
3-dehydroshikimic acid [Wiki]
3-DHS
More...

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

C02637 [DBID]
CHEBI:30918 [DBID]

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

Density: 1.7±0.1 g/cm3
Boiling Point: 405.1±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 75.9±6.0 kJ/mol
Flash Point: 213.0±25.2 °C
Index of Refraction: 1.651
Molar Refractivity: 36.7±0.3 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: -1.10
ACD/LogD (pH 5.5): -3.51
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.65
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 95 Å2
Polarizability: 14.5±0.5 10-24cm3
Surface Tension: 105.5±3.0 dyne/cm
Molar Volume: 100.5±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) =  0.98

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  368.87  (Adapted Stein & Brown method)
    Melting Pt (deg C):  133.85  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.51E-008  (Modified Grain method)
    Subcooled liquid VP: 6.83E-007 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):  2.167e+004
       log Kow used: 0.98 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  7.0881e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.40E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.759E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.98  (KowWin est)
  Log Kaw used:  -10.582  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.562
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0626
   Biowin2 (Non-Linear Model)     :   0.9521
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.4808  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.2216  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8720
   Biowin6 (MITI Non-Linear Model):   0.8233
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7819
 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):  9.11E-005 Pa (6.83E-007 mm Hg)
  Log Koa (Koawin est  ): 11.562
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0329 
       Octanol/air (Koa) model:  0.0895 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.543 
       Mackay model           :  0.725 
       Octanol/air (Koa) model:  0.877 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  68.1577 E-12 cm3/molecule-sec
      Half-Life =     0.157 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.883 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   Fraction sorbed to airborne particulates (phi): 0.634 (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]:
    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: 0.98 (estimated)

 Volatilization from Water:
    Henry LC:  6.4E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:   1.2E+009  hours   (5.001E+007 days)
    Half-Life from Model Lake : 1.309E+010  hours   (5.456E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               1.88  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.79  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       5.16e-005       3.26         1000       
   Water     31.2            208          1000       
   Soil      68.7            416          1000       
   Sediment  0.0586          1.87e+003    0          
     Persistence Time: 401 hr

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