ChemSpider 2D Image | arugosin C | C25H28O6

arugosin C

  • Molecular FormulaC25H28O6
  • Average mass424.486 Da
  • Monoisotopic mass424.188599 Da
  • ChemSpider ID166008

More details:






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

6,8-Dihydroxy-1-(2-hydroxy-2-propanyl)-4-methyl-9-(3-methyl-2-buten-1-yl)-1,12a-dihydrochromeno[4,5-bc][1]benzoxepin-7(2H)-on [German] [ACD/IUPAC Name]
6,8-Dihydroxy-1-(2-hydroxy-2-propanyl)-4-methyl-9-(3-methyl-2-buten-1-yl)-1,12a-dihydrochromeno[4,5-bc][1]benzoxepin-7(2H)-one [ACD/IUPAC Name]
6,8-Dihydroxy-1-(2-hydroxy-2-propanyl)-4-méthyl-9-(3-méthyl-2-butén-1-yl)-1,12a-dihydrochroméno[4,5-bc][1]benzoxépin-7(2H)-one [French] [ACD/IUPAC Name]
6,8-Dihydroxy-1-(2-hydroxypropan-2-yl)-4-methyl-9-(3-methylbut-2-en-1-yl)-1,12a-dihydrochromeno[4,5-bc][1]benzoxepin-7(2H)-one
arugosin C
Benzo[c]pyrano[2,3,4-jk][2]benzoxepin-7(2H)-one, 1,12a-dihydro-6,8-dihydroxy-1-(1-hydroxy-1-methylethyl)-4-methyl-9-(3-methyl-2-buten-1-yl)- [ACD/Index Name]
[1]BENZOPYRANO[4,5-BC][1]BENZOXEPIN-7(2H)-ONE,1,12A-DIHYDRO-6,8-DIHYDROXY-1-(1-HYDROXY- 1-METHYLETHYL)-4-METHYL-9-(3-METHYL-2- BUTENYL)-
1,12a-Dihydro-6,8-dihydroxy-1-(1-hydroxy-1-methylethyl)-4-methyl-9-(3-methylbut-2-enyl)(1)benzopy rano(4,5-bc)(1)benzoxepin-7(2H)-one
1,12a-dihydro-6,8-dihydroxy-1-(1-hydroxy-1-methylethyl)-4-methyl-9-(3-methylbut-2-enyl)(1)benzopyrano(4,5-bc)(1)benzoxepin-7(2H)-one
50875-10-0 [RN]
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  • Miscellaneous
    • Chemical Class:

      An organic heterotetracyclic compound that is 1,12a-dihydrochromeno[4,5-<ital>bc</ital>][1]benzoxepin-7(2<element>H</element>)-one substituted by a hydroxy group at position 8, a 2-hydroxypropan-2-yl group at position 1, a methyl group at position 4 and a prenyl group at position 9. Isolated from <ital>Aspergillus</ital>, it exhibits inhibitory activity against hepatitis C protease. ChEBI CHEBI:68860
      An organic heterotetracyclic compound that is 1,12a-dihydrochromeno[4,5-bc][1]benzoxepin-7(2H)-one substituted by a hydroxy group at position 8, a 2-hydroxypropan-2-yl ; group at position 1, a methyl group at position 4 and a prenyl group at position 9. Isolated from Aspergillus, it exhibits inhibitory activity against hepatitis C protease. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:68860

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

Density: 1.3±0.1 g/cm3
Boiling Point: 626.6±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 97.5±3.0 kJ/mol
Flash Point: 213.6±25.0 °C
Index of Refraction: 1.621
Molar Refractivity: 116.2±0.3 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 1
ACD/LogP: 6.66
ACD/LogD (pH 5.5): 5.76
ACD/BCF (pH 5.5): 13917.38
ACD/KOC (pH 5.5): 32071.32
ACD/LogD (pH 7.4): 5.45
ACD/BCF (pH 7.4): 6883.30
ACD/KOC (pH 7.4): 15861.93
Polar Surface Area: 96 Å2
Polarizability: 46.1±0.5 10-24cm3
Surface Tension: 55.1±3.0 dyne/cm
Molar Volume: 330.2±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) =  6.94

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  580.40  (Adapted Stein & Brown method)
    Melting Pt (deg C):  250.15  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.16E-015  (Modified Grain method)
    Subcooled liquid VP: 6.07E-013 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):  0.00245
       log Kow used: 6.94 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.75684 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Phenols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.41E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.924E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.94  (KowWin est)
  Log Kaw used:  -12.464  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.404
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9731
   Biowin2 (Non-Linear Model)     :   0.9066
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8733  (months      )
   Biowin4 (Primary Survey Model) :   3.1562  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1942
   Biowin6 (MITI Non-Linear Model):   0.0207
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5917
 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):  8.09E-011 Pa (6.07E-013 mm Hg)
  Log Koa (Koawin est  ): 19.404
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.71E+004 
       Octanol/air (Koa) model:  6.22E+006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 342.9957 E-12 cm3/molecule-sec
      Half-Life =     0.031 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    22.453 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    43.000000 E-17 cm3/molecule-sec
      Half-Life =     0.027 Days (at 7E11 mol/cm3)
      Half-Life =     38.378 Min
   Reaction With Nitrate Radicals May Be Important!
   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    :  1.91E+004
      Log Koc:  4.281 

 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 = 3.802 (BCF = 6332)
       log Kow used: 6.94 (estimated)

 Volatilization from Water:
    Henry LC:  8.41E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.434E+011  hours   (5.976E+009 days)
    Half-Life from Model Lake : 1.565E+012  hours   (6.52E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              93.82  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.04  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       0.00332         0.345        1000       
   Water     1.58            1.44e+003    1000       
   Soil      31.7            2.88e+003    1000       
   Sediment  66.7            1.3e+004     0          
     Persistence Time: 4.63e+003 hr




                    

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