ChemSpider 2D Image | Deoxyandrographolide | C20H30O4

Deoxyandrographolide

  • Molecular FormulaC20H30O4
  • Average mass334.450 Da
  • Monoisotopic mass334.214417 Da
  • ChemSpider ID10295017

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

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

2(5H)-Furanone, 3-[2-[(4aS,5R,6R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-1-naphthalenyl]ethyl]- [ACD/Index Name]
3-{2-[(4aS,5R,6R,8aR)-6-Hydroxy-5-(hydroxyméthyl)-2,5,8a-triméthyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphtalényl]éthyl}-2(5H)-furanone [French] [ACD/IUPAC Name]
3-{2-[(4aS,5R,6R,8aR)-6-Hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalenyl]ethyl}-2(5H)-furanone [ACD/IUPAC Name]
3-{2-[(4aS,5R,6R,8aR)-6-Hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalinyl]ethyl}-2(5H)-furanon [German] [ACD/IUPAC Name]
3-{2-[(4aS,5R,6R,8aR)-6-Hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]ethyl}furan-2(5H)-one
Deoxyandrographolide
[79233-15-1] [RN]
3-(2-((4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)ethyl)furan-2(5H)-one
4-[2-[(4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl]-2H-furan-5-one
79233-15-1 [RN]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Bio Activity:

      Deoxyandrographolide is a natural compound extracted from A. MedChem Express http://www.medchemexpress.com/Gomisin-G.html, HY-N0857
      Deoxyandrographolide is a natural compound extracted from A. paniculata; potently inhibit the growth of liver (HepG2 and SK-Hep1) and bile duct (HuCCA-1 and RMCCA-1) cancer cells.;IC50 value:;Target: Anticancer natural compound;In vitro: Treatment with 14-DAG activated AMPK through induction of cyclic AMP-protein kinase A pathway. 14-DAG controlled ethanol-induced hepatosteatosis by interfering with dysregulation of lipid metabolism. In conclusion, our results indicated that 14-DAG was capable of preventing the development of fatty liver through AMPK-mediated regulation of lipid metabolism [1]. 14-DAG down-regulated the formation of death-inducing signalling complex, resulting in desensitization of hepatocytes to TNF-alpha-induced apoptosis. Pretreatment of hepatocytes with 14-DAG accentuated microsomal Ca-ATPase activity through induction of NO/cGMP pathway [2]. 14-DAP, in concentrations between 10-100 microM, reduced the extracellular acidification rate and the intracellular alka MedChem Express HY-N0857
      Others MedChem Express HY-N0857

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

Density: 1.1±0.1 g/cm3
Boiling Point: 511.7±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.0 mmHg at 25°C
Enthalpy of Vaporization: 90.1±6.0 kJ/mol
Flash Point: 178.2±23.6 °C
Index of Refraction: 1.535
Molar Refractivity: 92.6±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 2.55
ACD/LogD (pH 5.5): 3.36
ACD/BCF (pH 5.5): 208.83
ACD/KOC (pH 5.5): 1592.61
ACD/LogD (pH 7.4): 3.36
ACD/BCF (pH 7.4): 208.83
ACD/KOC (pH 7.4): 1592.61
Polar Surface Area: 67 Å2
Polarizability: 36.7±0.5 10-24cm3
Surface Tension: 41.4±3.0 dyne/cm
Molar Volume: 297.6±3.0 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):  483.24  (Adapted Stein & Brown method)
    Melting Pt (deg C):  200.47  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.87E-012  (Modified Grain method)
    Subcooled liquid VP: 2.04E-010 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):  8.053
       log Kow used: 3.49 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  44.935 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylates

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.68E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.568E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.49  (KowWin est)
  Log Kaw used:  -7.163  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.653
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7121
   Biowin2 (Non-Linear Model)     :   0.7555
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4960  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5462  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7976
   Biowin6 (MITI Non-Linear Model):   0.6039
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1504
 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):  2.72E-008 Pa (2.04E-010 mm Hg)
  Log Koa (Koawin est  ): 10.653
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  110 
       Octanol/air (Koa) model:  0.011 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.469 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 167.7111 E-12 cm3/molecule-sec
      Half-Life =     0.064 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.765 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    55.453121 E-17 cm3/molecule-sec
      Half-Life =     0.021 Days (at 7E11 mol/cm3)
      Half-Life =     29.759 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    :  198.5
      Log Koc:  2.298 

 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 = 1.986 (BCF = 96.93)
       log Kow used: 3.49 (estimated)

 Volatilization from Water:
    Henry LC:  1.68E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.373E+005  hours   (2.656E+004 days)
    Half-Life from Model Lake : 6.953E+006  hours   (2.897E+005 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       0.0166          0.375        1000       
   Water     18              900          1000       
   Soil      80.7            1.8e+003     1000       
   Sediment  1.27            8.1e+003     0          
     Persistence Time: 1.07e+003 hr

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