ChemSpider 2D Image | Australifungin | C23H36O6

Australifungin

  • 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)-
Australifungin
(4S,4aR,5S,7R,8R,8aS)-2,5,8-trihydroxy-4-[(2Z)-3-hydroxyprop-2-enoyl]-4,7-dimethyl-3-[(2R)-octan-2-yl]-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65459

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 https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65459

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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