ChemSpider 2D Image | (+)-Deoxyfrenolicin | C18H18O6

(+)-Deoxyfrenolicin

  • Molecular FormulaC18H18O6
  • Average mass330.332 Da
  • Monoisotopic mass330.110352 Da
  • ChemSpider ID2341174

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(+)-Deoxyfrenolicin
[(1R,3S)-9-Hydroxy-5,10-dioxo-1-propyl-3,4,5,10-tetrahydro-1H-benzo[g]isochromen-3-yl]acetic acid [ACD/IUPAC Name]
[(1R,3S)-9-Hydroxy-5,10-dioxo-1-propyl-3,4,5,10-tetrahydro-1H-benzo[g]isochromen-3-yl]essigsäure [German] [ACD/IUPAC Name]
10023-11-7 [RN]
1H-Naphtho[2,3-c]pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-5,10-dioxo-1-propyl-, (1R,3S)- [ACD/Index Name]
Acide [(1R,3S)-9-hydroxy-5,10-dioxo-1-propyl-3,4,5,10-tétrahydro-1H-benzo[g]isochromén-3-yl]acétique [French] [ACD/IUPAC Name]
Deoxyfrenolicin
L0RG5J840S
[(1R,3S)-9-HYDROXY-5,10-DIOXO-1-PROPYL-1H,3H,4H-NAPHTHO[2,3-C]PYRAN-3-YL]ACETIC ACID
1H-Naphtho(2,3-c)pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-5,10-dioxo-1-propyl-, (1R-trans)-
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Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.4±0.1 g/cm3
Boiling Point: 604.9±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 94.6±3.0 kJ/mol
Flash Point: 223.5±25.0 °C
Index of Refraction: 1.624
Molar Refractivity: 82.8±0.4 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 3.66
ACD/LogD (pH 5.5): 2.13
ACD/BCF (pH 5.5): 11.56
ACD/KOC (pH 5.5): 81.99
ACD/LogD (pH 7.4): -0.36
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 101 Å2
Polarizability: 32.8±0.5 10-24cm3
Surface Tension: 66.0±5.0 dyne/cm
Molar Volume: 234.3±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) =  3.25

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  517.21  (Adapted Stein & Brown method)
    Melting Pt (deg C):  220.64  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.71E-012  (Modified Grain method)
    Subcooled liquid VP: 1.2E-009 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):  129.7
       log Kow used: 3.25 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2495.9 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Phenols-acid
       Vinyl/Allyl Ethers-acid
       Quinone/Hydroquinone-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.55E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.254E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.25  (KowWin est)
  Log Kaw used:  -14.511  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.761
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4451
   Biowin2 (Non-Linear Model)     :   0.0114
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8365  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7422  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4296
   Biowin6 (MITI Non-Linear Model):   0.1014
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2665
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  1.6E-007 Pa (1.2E-009 mm Hg)
  Log Koa (Koawin est  ): 17.761
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  18.8 
       Octanol/air (Koa) model:  1.42E+005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  64.1397 E-12 cm3/molecule-sec
      Half-Life =     0.167 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.001 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.393750 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.720 Hrs
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  15.58
      Log Koc:  1.193 

 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: 3.25 (estimated)

 Volatilization from Water:
    Henry LC:  7.55E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.409E+013  hours   (5.873E+011 days)
    Half-Life from Model Lake : 1.538E+014  hours   (6.407E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               8.47  percent
    Total biodegradation:        0.15  percent
    Total sludge adsorption:     8.33  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       1.42e-006       1.93         1000       
   Water     16.4            360          1000       
   Soil      83.1            720          1000       
   Sediment  0.443           3.24e+003    0          
     Persistence Time: 780 hr

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