ChemSpider 2D Image | Gedunin | C28H34O7

Gedunin

  • Molecular FormulaC28H34O7
  • Average mass482.565 Da
  • Monoisotopic mass482.230438 Da
  • ChemSpider ID10176979

  • defined stereocentres - 9 of 9 defined stereocentres

More details:

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

(1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-1-(Furan-3-yl)-4b,7,7,10a,12a-pentamethyl-3,8-dioxo-1,3,3a,4b,5,6,6a,7,8,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]oxireno[2,3-d]isochromen-5-yl acetate
(4aR,6R,6aS,6bR,7aS,10S,10aS,12aR,12bR)-10-(3-Furyl)-4,4,6a,10a,12b-pentamethyl-3,8-dioxo-3,4,4a,5,6,6a,7a,8,10,10a,11,12,12a,12b-tetradecahydronaphtho[2,1-f]oxireno[d]isochromen-6-yl acetate [ACD/IUPAC Name]
(4aR,6R,6aS,6bR,7aS,10S,10aS,12aR,12bR)-10-(3-Furyl)-4,4,6a,10a,12b-pentamethyl-3,8-dioxo-3,4,4a,5,6,6a,7a,8,10,10a,11,12,12a,12b-tetradecahydronaphtho[2,1-f]oxireno[d]isochromen-6-yl-acetat [German] [ACD/IUPAC Name]
2753-30-2 [RN]
Acétate de (4aR,6R,6aS,6bR,7aS,10S,10aS,12aR,12bR)-10-(3-furyl)-4,4,6a,10a,12b-pentaméthyl-3,8-dioxo-3,4,4a,5,6,6a,7a,8,10,10a,11,12,12a,12b-tétradécahydronaphto[2,1-f]oxiréno[d]isochromén-6-yle [French] [ACD/IUPAC Name]
Gedunin
Oxireno[c]phenanthro[1,2-d]pyran-3,8(4H,7aH)-dione, 6-(acetyloxy)-10-(3-furanyl)-4a,5,6,6a,10,10a,11,12,12a,12b-decahydro-4,4,6a,10a,12b-pentamethyl-, (4aR,6R,6aS,6bR,7aS,10S,10aS,12aR,12bR)- [ACD/Index Name]
(-)-gedunin
(1S,2R,4S,7R,8S,11R,12R,17R,19R)-7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.02,4.02,8.012,17]nonadec-13-en-19-yl acetate
(1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-5-(Acetyloxy)-1-(3-furanyl)-1,5,6,6a,7,10a,10b,11,12,12a,decahydro-4b,7,7,10a,12a,-pentamethyloxireno[c]phenanthro[1,2-d]pyran-3,8(3aH,4bH)-dione
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

MLS000563507 [DBID]
NSC 113497 [DBID]
SMR000232316 [DBID]
  • Experimental Physico-chemical Properties

    • Experimental Solubility:

      Soluble to 100 mM in DMSO and to 10 mM in ethanol Tocris Bioscience 3387
      Soluble to 100 mM in DMSO and to 10 mM in ethanol with gentle warming Tocris Bioscience 3387
  • Miscellaneous

    • Chemical Class:

      A pentacyclic triterpenoid natural product found particularly in <ital>Azadirachta indica</ital> and <ital>Cedrela odorata</ital>. ChEBI CHEBI:65954
      A pentacyclic triterpenoid natural product found particularly in Azadirachta indica and Cedrela odorata. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65954, CHEBI:65954

    • Bio Activity:

      Cell Biology Tocris Bioscience 3387
      Heat Shock Proteins Tocris Bioscience 3387
      Hsp90 Tocris Bioscience 3387
      Hsp90 inhibitor; exhibits anticancer and antimalarial activity Tocris Bioscience 3387
      Naturally occurring Hsp90 inhibitor. Induces Hsp90-dependent client protein degradation and displays antiproliferative activity in vitro (IC50 values are 3.22, 8.84 and 16.8 ?M in SKBr3, MCF-7 and CaC o-2 cancer cell lines respectively). Also exhibits antimalarial activity against P. falciparum (IC50 values are 0.14 and 3.1 ?M in parasite development and [3H]-hypoxanthine uptake assays respectively ). Tocris Bioscience 3387
      Naturally occurring Hsp90 inhibitor. Induces Hsp90-dependent client protein degradation and displays antiproliferative activity in vitro (IC50 values are 3.22, 8.84 and 16.8 ?M in SKBr3, MCF-7 and CaCo-2 cancer cell lines respectively). Also exhibits antimalarial activity against P. falciparum (IC50 values are 0.14 and 3.1 ?M in parasite development and [3H]-hypoxanthine uptake assays respectively). Tocris Bioscience 3387
      Naturally occurring Hsp90 inhibitor. Induces Hsp90-dependent client protein degradation and displays antiproliferative activity in vitro (IC50 values are 3.22, 8.84 and 16.8 muM in SKBr3, MCF-7 and CaCo-2 cancer cell lines respectively). Decreases ovarian cancer cell proliferation in vitro and may enhance cisplatin-induced reduction in proliferation (CAT.No 3387). Also exhibits antimalarial activity against P. falciparum (IC50 values are 0.14 and 3.1 muM in parasite development and [3H]-hypoxanthine uptake assays respectively). Tocris Bioscience 3387
      Signal Transduction Tocris Bioscience 3387

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

Density: 1.3±0.1 g/cm3
Boiling Point: 594.3±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 88.6±3.0 kJ/mol
Flash Point: 313.2±30.1 °C
Index of Refraction: 1.581
Molar Refractivity: 125.6±0.4 cm3
#H bond acceptors: 7
#H bond donors: 0
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 3.34
ACD/LogD (pH 5.5): 3.57
ACD/BCF (pH 5.5): 303.64
ACD/KOC (pH 5.5): 2082.01
ACD/LogD (pH 7.4): 3.57
ACD/BCF (pH 7.4): 303.64
ACD/KOC (pH 7.4): 2082.01
Polar Surface Area: 95 Å2
Polarizability: 49.8±0.5 10-24cm3
Surface Tension: 51.4±5.0 dyne/cm
Molar Volume: 376.6±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) =  3.49

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  555.60  (Adapted Stein & Brown method)
    Melting Pt (deg C):  238.57  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.15E-012  (Modified Grain method)
    Subcooled liquid VP: 1.04E-009 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):  0.9604
       log Kow used: 3.49 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.47511 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.31E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.405E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.49  (KowWin est)
  Log Kaw used:  -10.754  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.244
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.3940
   Biowin2 (Non-Linear Model)     :   0.0003
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.3214  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.8103  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5599
   Biowin6 (MITI Non-Linear Model):   0.0571
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.2204
 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):  1.39E-007 Pa (1.04E-009 mm Hg)
  Log Koa (Koawin est  ): 14.244
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  21.6 
       Octanol/air (Koa) model:  43.1 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 176.5163 E-12 cm3/molecule-sec
      Half-Life =     0.061 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.727 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.175000 E-17 cm3/molecule-sec
      Half-Life =     6.549 Days (at 7E11 mol/cm3)
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.514E+004
      Log Koc:  4.180 

 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 = 1.990 (BCF = 97.83)
       log Kow used: 3.49 (estimated)

 Volatilization from Water:
    Henry LC:  4.31E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.984E+009  hours   (1.243E+008 days)
    Half-Life from Model Lake : 3.255E+010  hours   (1.356E+009 days)

 Removal In Wastewater Treatment:
    Total removal:              12.81  percent
    Total biodegradation:        0.18  percent
    Total sludge adsorption:    12.62  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       0.00098         1.44         1000       
   Water     5               4.32e+003    1000       
   Soil      94.5            8.64e+003    1000       
   Sediment  0.529           3.89e+004    0          
     Persistence Time: 7.21e+003 hr

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