ChemSpider 2D Image | CHAETOVIRIDIN A | C23H25ClO6

CHAETOVIRIDIN A

  • Molecular FormulaC23H25ClO6
  • Average mass432.894 Da
  • Monoisotopic mass432.133972 Da
  • ChemSpider ID4953135
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 4 of 4 defined stereocentres


More details:






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

(6aS)-5-Chlor-9-[(2S,3R)-3-hydroxy-2-methylbutanoyl]-6a-methyl-3-[(1E,3S)-3-methyl-1-penten-1-yl]-6H-furo[2,3-h]isochromen-6,8(6aH)-dion [German] [ACD/IUPAC Name]
(6aS)-5-Chloro-9-[(2S,3R)-3-hydroxy-2-methylbutanoyl]-6a-methyl-3-[(1E,3S)-3-methyl-1-penten-1-yl]-6H-furo[2,3-h]isochromene-6,8(6aH)-dione [ACD/IUPAC Name]
(6aS)-5-Chloro-9-[(2S,3R)-3-hydroxy-2-méthylbutanoyl]-6a-méthyl-3-[(1E,3S)-3-méthyl-1-pentén-1-yl]-6H-furo[2,3-h]isochromène-6,8(6aH)-dione [French] [ACD/IUPAC Name]
(6aS)-5-Chloro-9-[(2S,3R)-3-hydroxy-2-methylbutanoyl]-6a-methyl-3-[(1E,3S)-3-methylpent-1-en-1-yl]-6H-furo[2,3-h]isochromene-6,8(6aH)-dione
6H-Furo[2,3-h]-2-benzopyran-6,8(6aH)-dione, 5-chloro-9-[(2S,3R)-3-hydroxy-2-methyl-1-oxobutyl]-6a-methyl-3-[(1E,3S)-3-methyl-1-penten-1-yl]-, (6aS)- [ACD/Index Name]
CHAETOVIRIDIN A
(6AS)-5-CHLORO-9-[(2S,3R)-3-HYDROXY-2-METHYLBUTANOYL]-6A-METHYL-3-[(1E,3S)-3-METHYLPENT-1-EN-1-YL]-6H,6AH,8H-FURO[2,3-H]ISOCHROMENE-6,8-DIONE
(6AS)-5-CHLORO-9-[(2S,3R)-3-HYDROXY-2-METHYLBUTANOYL]-6A-METHYL-3-[(1E,3S)-3-METHYLPENT-1-EN-1-YL]FURO[2,3-H]ISOCHROMENE-6,8-DIONE
1267888-95-8 [RN]
128252-98-2 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS092944 [DBID]
AIDS-092944 [DBID]
CCRIS 7226 [DBID]
  • Miscellaneous
    • Chemical Class:

      An azaphilone that is 6<element>H</element>-furo[2,3-<ital>h</ital>]isochromene-6,8(6a<element>H</element>)-dione substituted by a chloro group at position 5, a 3-hydroxy-2-methylbutanoyl group at p osition 9, a methyl group at position 6a and a 3-methylpent-1-en-1yl group at position 3. Isolated from <ital>Chaetomium globosum</ital>, it exhibits natifungal activity against plant pathogenic fungi . ChEBI CHEBI:67610

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

Density: 1.3±0.1 g/cm3
Boiling Point: 607.6±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.9 mmHg at 25°C
Enthalpy of Vaporization: 103.6±6.0 kJ/mol
Flash Point: 321.3±31.5 °C
Index of Refraction: 1.588
Molar Refractivity: 110.7±0.4 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 1.22
ACD/LogD (pH 5.5): 1.73
ACD/BCF (pH 5.5): 12.23
ACD/KOC (pH 5.5): 208.91
ACD/LogD (pH 7.4): 1.73
ACD/BCF (pH 7.4): 12.23
ACD/KOC (pH 7.4): 208.91
Polar Surface Area: 90 Å2
Polarizability: 43.9±0.5 10-24cm3
Surface Tension: 51.3±5.0 dyne/cm
Molar Volume: 329.2±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) =  3.69

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  558.86  (Adapted Stein & Brown method)
    Melting Pt (deg C):  240.09  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.35E-014  (Modified Grain method)
    Subcooled liquid VP: 2.86E-012 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):  4.342
       log Kow used: 3.69 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  10.444 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.78E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.771E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.69  (KowWin est)
  Log Kaw used:  -12.811  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.501
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2453
   Biowin2 (Non-Linear Model)     :   0.0029
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1038  (months      )
   Biowin4 (Primary Survey Model) :   3.2733  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1590
   Biowin6 (MITI Non-Linear Model):   0.0077
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.4127
 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):  3.81E-010 Pa (2.86E-012 mm Hg)
  Log Koa (Koawin est  ): 16.501
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.87E+003 
       Octanol/air (Koa) model:  7.78E+003 
   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 = 274.8915 E-12 cm3/molecule-sec
      Half-Life =     0.039 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    28.015 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     6.100025 E-17 cm3/molecule-sec
      Half-Life =     0.188 Days (at 7E11 mol/cm3)
      Half-Life =      4.509 Hrs
   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    :  18.82
      Log Koc:  1.275 

 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 = 2.143 (BCF = 139)
       log Kow used: 3.69 (estimated)

 Volatilization from Water:
    Henry LC:  3.78E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.223E+011  hours   (1.343E+010 days)
    Half-Life from Model Lake : 3.516E+012  hours   (1.465E+011 days)

 Removal In Wastewater Treatment:
    Total removal:              18.13  percent
    Total biodegradation:        0.22  percent
    Total sludge adsorption:    17.90  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       0.00632         0.774        1000       
   Water     10.3            1.44e+003    1000       
   Soil      88.2            2.88e+003    1000       
   Sediment  1.44            1.3e+004     0          
     Persistence Time: 2.36e+003 hr




                    

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