ChemSpider 2D Image | Arisugacin A | C28H32O8

Arisugacin A

  • Molecular FormulaC28H32O8
  • Average mass496.549 Da
  • Monoisotopic mass496.209717 Da
  • ChemSpider ID8430760
  • defined stereocentres - 4 of 4 defined stereocentres


More details:






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

(4aR,6aR,12aS,12bS)-9-(3,4-Dimethoxyphenyl)-4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-4a,6,6a,12,12a,12b-hexahydro-4H,11H-benzo[f]pyrano[4,3-b]chromen-1,11(5H)-dion [German] [ACD/IUPAC Name]
(4aR,6aR,12aS,12bS)-9-(3,4-Dimethoxyphenyl)-4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-4a,6,6a,12,12a,12b-hexahydro-4H,11H-benzo[f]pyrano[4,3-b]chromene-1,11(5H)-dione [ACD/IUPAC Name]
(4aR,6aR,12aS,12bS)-9-(3,4-Diméthoxyphényl)-4a,12a-dihydroxy-4,4,6a,12b-tétraméthyl-4a,6,6a,12,12a,12b-hexahydro-4H,11H-benzo[f]pyrano[4,3-b]chromène-1,11(5H)-dione [French] [ACD/IUPAC Name]
4H,11H-Naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(5H)-dione, 9-(3,4-dimethoxyphenyl)-4a,6,6a,12,12a,12b-hexahydro-4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-, (4aR,6aR,12aS,12bS)- [ACD/Index Name]
Arisugacin A [Wiki]
9-(3,4-Dimethoxy-phenyl)-4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-4a,6,6a,12,12a,12b-hexahydro-4H,5H-7,10-dioxa-benzo[a]anthracene-1,11-dione
arisugacin
CHEMBL283509
  • Miscellaneous
    • Chemical Class:

      An organic heterotetracyclic compound that is 4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-4a,6,6a,12,12a,12b-hexahydro-4<element>H</element>,11<element>H</element>-benzo[<ital>f</ital>]pyrano[4,3-<ital>b< /ital>]chromene-1,11(5<element>H</element>)-dione substituted by 3,4-dimethoxyphenyl group at position 9 (the 4a<stereo>R</stereo>,6a<stereo>R</stereo>,12a<stereo>S</stereo>,12b<element>S</element> st eroisomer). Isolated from the culture broth of <ital>Penicillium</ital>, it acts as a selective inhibitor of acetylcholinesterase. ChEBI CHEBI:65435
      An organic heterotetracyclic compound that is 4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-4a,6,6a,12,12a,12b-hexahydro-4H,11H-benzo[f]pyrano[4,3-<ital>b<; /ital>]chromene-1,11(5H)-dione substituted by 3,4 -dimethoxyphenyl group at position 9 (the 4aR,6aR,12aS,12bS st; eroisomer). Isolated from the culture broth of Penicillium, it acts as a selective inhibitor of acetylcholinesterase. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65435

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

Density: 1.4±0.1 g/cm3
Boiling Point: 671.3±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 103.6±3.0 kJ/mol
Flash Point: 222.1±25.0 °C
Index of Refraction: 1.626
Molar Refractivity: 129.8±0.4 cm3
#H bond acceptors: 8
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 3.26
ACD/LogD (pH 5.5): 3.43
ACD/BCF (pH 5.5): 239.00
ACD/KOC (pH 5.5): 1754.15
ACD/LogD (pH 7.4): 3.43
ACD/BCF (pH 7.4): 239.00
ACD/KOC (pH 7.4): 1754.11
Polar Surface Area: 112 Å2
Polarizability: 51.5±0.5 10-24cm3
Surface Tension: 60.5±5.0 dyne/cm
Molar Volume: 366.6±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) =  0.63

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  632.71  (Adapted Stein & Brown method)
    Melting Pt (deg C):  274.59  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.33E-018  (Modified Grain method)
    Subcooled liquid VP: 3E-015 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):  219.9
       log Kow used: 0.63 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  7.6268 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.73E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.584E-020 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.63  (KowWin est)
  Log Kaw used:  -15.630  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.260
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.3110
   Biowin2 (Non-Linear Model)     :   0.0003
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.0341  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.7154  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5312
   Biowin6 (MITI Non-Linear Model):   0.0615
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.3007
 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):  4E-013 Pa (3E-015 mm Hg)
  Log Koa (Koawin est  ): 16.260
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.5E+006 
       Octanol/air (Koa) model:  4.47E+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 = 213.1387 E-12 cm3/molecule-sec
      Half-Life =     0.050 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.602 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =   316.074982 E-17 cm3/molecule-sec
      Half-Life =     0.004 Days (at 7E11 mol/cm3)
      Half-Life =      5.221 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    :  24.68
      Log Koc:  1.392 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 0.63 (estimated)

 Volatilization from Water:
    Henry LC:  5.73E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.277E+014  hours   (9.487E+012 days)
    Half-Life from Model Lake : 2.484E+015  hours   (1.035E+014 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       0.00354         0.0812       1000       
   Water     56.2            4.32e+003    1000       
   Soil      43.7            8.64e+003    1000       
   Sediment  0.116           3.89e+004    0          
     Persistence Time: 1.01e+003 hr




                    

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