ChemSpider 2D Image | rotiorinol C | C23H26O6

rotiorinol C

  • Molecular FormulaC23H26O6
  • Average mass398.449 Da
  • Monoisotopic mass398.172943 Da
  • ChemSpider ID9878707

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 3 of 3 defined stereocentres

More details:

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

(9R,9aR)-3-Acetyl-9-hydroxy-6-[(1E,3E,5S)-7-hydroxy-3,5-dimethyl-1,3-heptadien-1-yl]-9a-methyl-9,9a-dihydro-2H-furo[3,2-g]isochromen-2-on [German] [ACD/IUPAC Name]
(9R,9aR)-3-Acetyl-9-hydroxy-6-[(1E,3E,5S)-7-hydroxy-3,5-dimethyl-1,3-heptadien-1-yl]-9a-methyl-9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one [ACD/IUPAC Name]
(9R,9aR)-3-Acétyl-9-hydroxy-6-[(1E,3E,5S)-7-hydroxy-3,5-diméthyl-1,3-heptadién-1-yl]-9a-méthyl-9,9a-dihydro-2H-furo[3,2-g]isochromén-2-one [French] [ACD/IUPAC Name]
2H-Furo[3,2-g][2]benzopyran-2-one, 3-acetyl-9,9a-dihydro-9-hydroxy-6-[(1E,3E,5S)-7-hydroxy-3,5-dimethyl-1,3-heptadien-1-yl]-9a-methyl-, (9R,9aR)- [ACD/Index Name]
901309-46-4 [RN]
rotiorinol C
(9R,9aR)-3-acetyl-9-hydroxy-6-[(1E,3E,5S)-7-hydroxy-3,5-dimethylhepta-1,3-dien-1-yl]-9a-methyl-9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one
6-acetyl-3-(3,5-dimethyl-1E,3E-heptadien-7-ol)-9R-hydroxy-8a(R)-methyl-7H-furo[2,3-g]-2-benzopyran-7-one
https://www.ebi.ac.uk/chembl/compoundreportcard/CHEMBL497093/
  • Miscellaneous

    • Chemical Class:

      An azaphilone that is 9,9a-dihydro-2<element>H</element>-furo[3,2-<ital>g</ital>]isochromen-2-one substituted by an acetyl group at position 3, a hydroxy group at position 9, a 7-hydroxy-3,5-dimethylh epta-1,3-dien-1-yl group at position 6 and a methyl group at position 9a. It has been isolated from <ital>Chaetomium cupreum</ital> and exhibits antifungal activity. ChEBI CHEBI:68786
      An azaphilone that is 9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one substituted by an acetyl group at position 3, a hydroxy group at position 9, a 7-hydroxy-3,5-dimethylh; epta-1,3-dien-1-yl group at po sition 6 and a methyl group at position 9a. It has been isolated from Chaetomium cupreum and exhibits antifungal activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:68786
      An azaphilone that is 9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one substituted by an acetyl group at position 3, a hydroxy group at position 9, a 7-hydroxy-3,5-dimethylhepta-1,3-dien-1-yl group at posi tion 6 and a methyl group at position 9a. It has been isolated from Chaetomium cupreum and exhibits antifungal activity. ChEBI CHEBI:68786

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

Density: 1.3±0.1 g/cm3
Boiling Point: 694.0±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.9 mmHg at 25°C
Enthalpy of Vaporization: 116.2±6.0 kJ/mol
Flash Point: 242.8±25.0 °C
Index of Refraction: 1.606
Molar Refractivity: 107.3±0.4 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: -0.47
ACD/LogD (pH 5.5): 0.80
ACD/BCF (pH 5.5): 2.38
ACD/KOC (pH 5.5): 64.70
ACD/LogD (pH 7.4): 0.80
ACD/BCF (pH 7.4): 2.38
ACD/KOC (pH 7.4): 64.70
Polar Surface Area: 93 Å2
Polarizability: 42.5±0.5 10-24cm3
Surface Tension: 54.0±5.0 dyne/cm
Molar Volume: 311.1±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) =  2.27

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  564.21  (Adapted Stein & Brown method)
    Melting Pt (deg C):  242.59  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.31E-015  (Modified Grain method)
    Subcooled liquid VP: 5.24E-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):  36
       log Kow used: 2.27 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  440.58 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.13E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.364E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.27  (KowWin est)
  Log Kaw used:  -11.335  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.605
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5250
   Biowin2 (Non-Linear Model)     :   0.1257
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5355  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5753  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4789
   Biowin6 (MITI Non-Linear Model):   0.0745
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5438
 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):  6.99E-011 Pa (5.24E-013 mm Hg)
  Log Koa (Koawin est  ): 13.605
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.29E+004 
       Octanol/air (Koa) model:  9.89 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 417.5635 E-12 cm3/molecule-sec
      Half-Life =     0.026 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    18.443 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    36.642502 E-17 cm3/molecule-sec
      Half-Life =     0.031 Days (at 7E11 mol/cm3)
      Half-Life =     45.036 Min
   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    :  10.75
      Log Koc:  1.031 

 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 = 1.049 (BCF = 11.18)
       log Kow used: 2.27 (estimated)

 Volatilization from Water:
    Henry LC:  1.13E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.034E+010  hours   (4.309E+008 days)
    Half-Life from Model Lake : 1.128E+011  hours   (4.701E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               2.59  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.49  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       0.0175          0.338        1000       
   Water     25.7            900          1000       
   Soil      74.2            1.8e+003     1000       
   Sediment  0.143           8.1e+003     0          
     Persistence Time: 909 hr

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