ChemSpider 2D Image | Australifungin | C23H36O6


  • Molecular FormulaC23H36O6
  • Average mass408.528 Da
  • Monoisotopic mass408.251190 Da
  • ChemSpider ID4440358
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 7 of 7 defined stereocentres

More details:

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

(4S,4aR,5S,7R,8R,8aS)-2,5,8-Trihydroxy-4-[(2Z)-3-hydroxy-2-propenoyl]-4,7-diméthyl-3-[(2R)-2-octanyl]-4a,5,6,7,8,8a-hexahydro-1(4H)-naphtalénone [French] [ACD/IUPAC Name]
(4S,4aR,5S,7R,8R,8aS)-2,5,8-Trihydroxy-4-[(2Z)-3-hydroxy-2-propenoyl]-4,7-dimethyl-3-[(2R)-2-octanyl]-4a,5,6,7,8,8a-hexahydro-1(4H)-naphthalenone [ACD/IUPAC Name]
(4S,4aR,5S,7R,8R,8aS)-2,5,8-Trihydroxy-4-[(2Z)-3-hydroxy-2-propenoyl]-4,7-dimethyl-3-[(2R)-2-octanyl]-4a,5,6,7,8,8a-hexahydro-1(4H)-naphthalinon [German] [ACD/IUPAC Name]
1(4H)-Naphthalenone, 4a,5,6,7,8,8a-hexahydro-2,5,8-trihydroxy-4-[(2Z)-3-hydroxy-1-oxo-2-propen-1-yl]-4,7-dimethyl-3-[(1R)-1-methylheptyl]-, (4S,4aR,5S,7R,8R,8aS)- [ACD/Index Name]
1(4H)-Naphthalenone, 4a,5,6,7,8,8a-hexahydro-2,5,8-trihydroxy-4-[(2Z)-3-hydroxy-1-oxo-2-propenyl]-4,7-dimethyl-3-[(1R)-1-methylheptyl]-, (4S,4aR,5S,7R,8R,8aS)-

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

AIDS231383 [DBID]
AIDS-231383 [DBID]
  • Miscellaneous
    • Chemical Class:

      A carbobicyclic compound that is 4a,5,6,7,8,8a-hexahydronaphthalen-1(4<element>H</element>)-one substituted by hydroxy groups at positions 2, 5 and 8, a (2<stereo>Z</stereo>)-3-hydroxyprop-2-enoyl gro up at position 4, methyl groups at positions 4 and 7 and a 2<stereo>R</stereo>-octan-2-yl group at position 3 (the 4<stereo>S</stereo>,4a<stereo>R</stereo>,5<stereo>S</stereo>,7<stereo>R</stereo>,8<st ereo>R</stereo>,8a<stereo>S</stereo> stereoisomer). It is isolated from the fermentation extracts of <ital>Sporormiella australis</ital> and exhibits antifungal activity by interfering with the fungal lipid metabolism. ChEBI CHEBI:65459
      A carbobicyclic compound that is 4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one substituted by hydroxy groups at positions 2, 5 and 8, a (2Z)-3-hydroxyprop-2-enoyl gro; up at position 4, methyl groups at positions 4 and 7 and a 2R-octan-2-yl group at position 3 (the 4S,4aR,5S,7R,8R,8aS stereoisomer). It is isolated from the fermentation extracts of Sporormiella australis and exhibits antifungal activ ity by interfering with the fungal lipid metabolism. ChEBI

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

Density: 1.2±0.1 g/cm3
Boiling Point: 611.0±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.0 mmHg at 25°C
Enthalpy of Vaporization: 104.1±6.0 kJ/mol
Flash Point: 337.3±28.0 °C
Index of Refraction: 1.549
Molar Refractivity: 110.4±0.3 cm3
#H bond acceptors: 6
#H bond donors: 4
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 4.38
ACD/LogD (pH 5.5): 2.66
ACD/BCF (pH 5.5): 35.62
ACD/KOC (pH 5.5): 235.02
ACD/LogD (pH 7.4): 0.86
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 3.76
Polar Surface Area: 115 Å2
Polarizability: 43.8±0.5 10-24cm3
Surface Tension: 49.9±3.0 dyne/cm
Molar Volume: 347.1±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) =  3.19

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  592.74  (Adapted Stein & Brown method)
    Melting Pt (deg C):  255.92  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.64E-017  (Modified Grain method)
    Subcooled liquid VP: 1.53E-014 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):  5.124
       log Kow used: 3.19 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.030253 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.12E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.868E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.19  (KowWin est)
  Log Kaw used:  -8.339  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.529
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1261
   Biowin2 (Non-Linear Model)     :   0.7095
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9775  (weeks       )
   Biowin4 (Primary Survey Model) :   3.8473  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7368
   Biowin6 (MITI Non-Linear Model):   0.1956
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4926
 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):  2.04E-012 Pa (1.53E-014 mm Hg)
  Log Koa (Koawin est  ): 11.529
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.47E+006 
       Octanol/air (Koa) model:  0.083 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.869 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 246.2271 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 253.0671 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.521 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.507 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.225000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     1.312500 E-17 cm3/molecule-sec [Trans-]
      Half-Life =    22.452 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =    20.955 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   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    :  214.8
      Log Koc:  2.332 

 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 = 1.756 (BCF = 56.96)
       log Kow used: 3.19 (estimated)

 Volatilization from Water:
    Henry LC:  1.12E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.057E+007  hours   (4.403E+005 days)
    Half-Life from Model Lake : 1.153E+008  hours   (4.803E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               7.67  percent
    Total biodegradation:        0.14  percent
    Total sludge adsorption:     7.53  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       0.0959          0.996        1000       
   Water     24.6            360          1000       
   Soil      74.7            720          1000       
   Sediment  0.59            3.24e+003    0          
     Persistence Time: 472 hr


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