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Search term: MF = 'C_{23}H_{26}O_{5}'
ChemSpider 2D Image | ROTIORINOL A | C23H26O5

ROTIORINOL A

  • Molecular FormulaC23H26O5
  • Average mass382.449 Da
  • Monoisotopic mass382.178009 Da
  • ChemSpider ID9792624

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 3 of 3 defined stereocentres

More details:

Featured data source
Natural Product Updates

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(9R,9aR)-3-Acetyl-6-[(1E,3E,5S)-3,5-dimethyl-1,3-heptadien-1-yl]-9-hydroxy-9a-methyl-9,9a-dihydro-2H-furo[3,2-g]isochromen-2-on [German] [ACD/IUPAC Name]
(9R,9aR)-3-Acetyl-6-[(1E,3E,5S)-3,5-dimethyl-1,3-heptadien-1-yl]-9-hydroxy-9a-methyl-9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one [ACD/IUPAC Name]
(9R,9aR)-3-Acétyl-6-[(1E,3E,5S)-3,5-diméthyl-1,3-heptadién-1-yl]-9-hydroxy-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-6-[(1E,3E,5S)-3,5-dimethyl-1,3-heptadien-1-yl]-9,9a-dihydro-9-hydroxy-9a-methyl-, (9R,9aR)- [ACD/Index Name]
901309-41-9 [RN]
ROTIORINOL A
(9R,9aR)-3-acetyl-6-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-9-hydroxy-9a-methyl-9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one
6-acetyl-3-(3,5-dimethyl-1E,3E-heptadienyl)-9R-hydroxy-8a(R)-methyl-7H-furo[2,3-g]-2-benzopyran-7-one
https://www.ebi.ac.uk/chembl/compoundreportcard/CHEMBL525184/
  • 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 3,5-dimethylhepta-1,3-d ien-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:68785
      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 3,5-dimethylhepta-1,3-d; ien-1-yl group at position 6 a nd 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:68785
      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 3,5-dimethylhepta-1,3-dien-1-yl group at position 6 and a methyl group at position 9a. It has been isolated from Chaetomium cupreum and exhibits antifungal activity. ChEBI CHEBI:68785

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

Density: 1.2±0.1 g/cm3
Boiling Point: 629.3±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.2 mmHg at 25°C
Enthalpy of Vaporization: 106.7±6.0 kJ/mol
Flash Point: 219.4±25.0 °C
Index of Refraction: 1.589
Molar Refractivity: 105.7±0.4 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 1.41
ACD/LogD (pH 5.5): 2.52
ACD/BCF (pH 5.5): 48.20
ACD/KOC (pH 5.5): 557.64
ACD/LogD (pH 7.4): 2.52
ACD/BCF (pH 7.4): 48.20
ACD/KOC (pH 7.4): 557.62
Polar Surface Area: 73 Å2
Polarizability: 41.9±0.5 10-24cm3
Surface Tension: 48.1±5.0 dyne/cm
Molar Volume: 313.8±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) =  3.33

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  520.76  (Adapted Stein & Brown method)
    Melting Pt (deg C):  222.30  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.34E-013  (Modified Grain method)
    Subcooled liquid VP: 4.32E-011 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):  18.24
       log Kow used: 3.33 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  17.408 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 :   3.09E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.215E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.33  (KowWin est)
  Log Kaw used:  -9.898  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.228
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3739
   Biowin2 (Non-Linear Model)     :   0.0557
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4109  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4690  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3164
   Biowin6 (MITI Non-Linear Model):   0.0301
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.7821
 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):  5.76E-009 Pa (4.32E-011 mm Hg)
  Log Koa (Koawin est  ): 13.228
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  521 
       Octanol/air (Koa) model:  4.15 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.997 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 413.3057 E-12 cm3/molecule-sec
      Half-Life =     0.026 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    18.633 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    :  192.6
      Log Koc:  2.285 

 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 = 1.863 (BCF = 73.03)
       log Kow used: 3.33 (estimated)

 Volatilization from Water:
    Henry LC:  3.09E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.706E+008  hours   (1.544E+007 days)
    Half-Life from Model Lake : 4.042E+009  hours   (1.684E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               9.71  percent
    Total biodegradation:        0.16  percent
    Total sludge adsorption:     9.55  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       0.0149          0.34         1000       
   Water     18.2            900          1000       
   Soil      80.9            1.8e+003     1000       
   Sediment  0.885           8.1e+003     0          
     Persistence Time: 1.06e+003 hr

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