ChemSpider 2D Image | aspyrone | C9H12O4

aspyrone

  • Molecular FormulaC9H12O4
  • Average mass184.189 Da
  • Monoisotopic mass184.073563 Da
  • ChemSpider ID146667

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

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

(5S,6R)-5-Hydroxy-6-methyl-3-[(2S,3S)-3-methyl-2-oxiranyl]-5,6-dihydro-2H-pyran-2-on [German] [ACD/IUPAC Name]
(5S,6R)-5-Hydroxy-6-methyl-3-[(2S,3S)-3-methyl-2-oxiranyl]-5,6-dihydro-2H-pyran-2-one [ACD/IUPAC Name]
(5S,6R)-5-Hydroxy-6-méthyl-3-[(2S,3S)-3-méthyl-2-oxiranyl]-5,6-dihydro-2H-pyran-2-one [French] [ACD/IUPAC Name]
(5S,6R)-5-Hydroxy-6-methyl-3-[(2S,3S)-3-methyloxiran-2-yl]-5,6-dihydro-2H-pyran-2-one
17398-00-4 [RN]
2H-Pyran-2-one, 5,6-dihydro-5-hydroxy-6-methyl-3-[(2S,3S)-3-methyloxiranyl]-, (5S,6R)- [ACD/Index Name]
aspyrone
(2R,3S)-3-hydroxy-2-methyl-5-[(2S,3S)-3-methyloxiran-2-yl]-2,3-dihydropyran-6-one
(5S,6R)-5,6-dihydro-5-hydroxy-6-methyl-3-[(2S,3S)-3-methyl-2-oxiranyl]-2H-pyran-2-one
2H-Pyran-2-one, 5,6-dihydro-5-hydroxy-6-methyl-3-(3-methyloxiranyl)- [ACD/Index Name]
More...
  • Miscellaneous

    • Chemical Class:

      A member of the class of 2-pyranones that is 5,6-dihydro-2H-pyran-2-one in which the hydrogens at positions 3, 5S and 6R are replaced by (2S,3S)-3-methyloxiran-2-yl, hydroxy and methyl groups, respect ively. It is a fungal metabolite isolated from Aspergillus melleus and exhibits nematicidal, antibacterial and antifungal properties. ChEBI CHEBI:156387

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

Density: 1.3±0.1 g/cm3
Boiling Point: 383.5±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 73.1±6.0 kJ/mol
Flash Point: 159.3±21.4 °C
Index of Refraction: 1.544
Molar Refractivity: 44.3±0.3 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: -0.61
ACD/LogD (pH 5.5): -0.15
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 19.64
ACD/LogD (pH 7.4): -0.15
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 19.64
Polar Surface Area: 59 Å2
Polarizability: 17.6±0.5 10-24cm3
Surface Tension: 48.5±3.0 dyne/cm
Molar Volume: 140.2±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) =  -1.14

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  330.36  (Adapted Stein & Brown method)
    Melting Pt (deg C):  82.07  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.4E-006  (Modified Grain method)
    Subcooled liquid VP: 1.89E-005 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):  1e+006
       log Kow used: -1.14 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3.0217e+005 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylates
       Epoxides
       Vinyl/Allyl Ethers
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.05E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.309E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.14  (KowWin est)
  Log Kaw used:  -9.367  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.227
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6454
   Biowin2 (Non-Linear Model)     :   0.8967
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0836  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9307  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7273
   Biowin6 (MITI Non-Linear Model):   0.5252
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8086
 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):  0.00252 Pa (1.89E-005 mm Hg)
  Log Koa (Koawin est  ): 8.227
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00119 
       Octanol/air (Koa) model:  4.14E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0412 
       Mackay model           :  0.087 
       Octanol/air (Koa) model:  0.0033 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  43.6414 E-12 cm3/molecule-sec
      Half-Life =     0.245 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.941 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
   Fraction sorbed to airborne particulates (phi): 0.0641 (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: -1.14 (estimated)

 Volatilization from Water:
    Henry LC:  1.05E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.568E+007  hours   (3.153E+006 days)
    Half-Life from Model Lake : 8.256E+008  hours   (3.44E+007 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       0.000258        2.28         1000       
   Water     39              360          1000       
   Soil      61              720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr

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