ChemSpider 2D Image | (20S)-Protopanaxadiol | C30H52O3

(20S)-Protopanaxadiol

  • Molecular FormulaC30H52O3
  • Average mass460.732 Da
  • Monoisotopic mass460.391632 Da
  • ChemSpider ID9388412

  • defined stereocentres - 10 of 10 defined stereocentres

More details:

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

(20S)-Protopanaxadiol
(1S,3aR,3bR,5aR,7S,9aR,9bR,11R,11aR)-1-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-hexadecahydro-1H-cyclopenta[a]phenanthrene-7,11-diol
(3β,12β)-Dammar-24-en-3,12,20-triol [German] [ACD/IUPAC Name]
(3β,12β)-Dammar-24-ene-3,12,20-triol [ACD/IUPAC Name]
(3β,12β)-Dammar-24-ène-3,12,20-triol [French] [ACD/IUPAC Name]
30636-90-9 [RN]
7755-01-3 [RN]
Dammar-24-ene-3,12,20-triol, (3β,12β)- [ACD/Index Name]
MFCD12032048 [MDL number]
Protopanaxadiol [Wiki]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A diastereomer of protopanaxadiol in which the 20-hydroxy substituent has been introduced at the <ital>pro</ital>-<stereo>S</stereo> position. ChEBI CHEBI:75950
      A diastereomer of protopanaxadiol in which the 20-hydroxy substituent has been introduced at the pro-S position. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:75950, CHEBI:75950

    • Bio Activity:

      (20S)-Protopanaxadiol (20-Epiprotopanaxadiol) is an aglycon metabolic derivative of the protopanaxadiol-type ginseng saponin; apoptosis inducer. MedChem Express
      (20S)-Protopanaxadiol (20-Epiprotopanaxadiol) is an aglycon metabolic derivative of the protopanaxadiol-type ginseng saponin; apoptosis inducer.; IC50 value:; Target: apoptosis inducer; (20S)-Protopan axadiol was used to induce cytotoxicity for two human glioma cell lines, SF188 and U87MG. MedChem Express HY-N0797
      (20S)-Protopanaxadiol (20-Epiprotopanaxadiol) is an aglycon metabolic derivative of the protopanaxadiol-type ginseng saponin; apoptosis inducer.;IC50 value:;Target: apoptosis inducer(20S)-Protopanaxadiol was used to induce cytotoxicity for two human glioma cell lines, SF188 and U87MG. For the SF188 cells, (20S)-Protopanaxadiol activated caspases-3, -8, -7, and -9 within 3 h and induced rapid apoptosis, which could be partially inhibited by a general caspase blocker and completely abolished when the caspase blocker was used in combination with an antioxidant. (20S)-Protopanaxadiol also induced cell death in U87MG cells but did not activate any caspases in these cells [1]. aPPD was able to inhibit P-gp activity as potently as verapamil on MDR cells. The blockage of P-gp activity was highly reversible as wash-out of aPPD resulted in an immediate recovery of P-gp activity. Unlike verapamil, aPPD did not affect ATPase activity of P-gp suggesting a different mechanism of action [2]. MedChem Express HY-N0797
      Apoptosis MedChem Express HY-N0797
      Apoptosis inducer MedChem Express HY-N0797
      Apoptosis; MedChem Express HY-N0797

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

Density: 1.0±0.1 g/cm3
Boiling Point: 559.5±40.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.5 mmHg at 25°C
Enthalpy of Vaporization: 96.7±6.0 kJ/mol
Flash Point: 226.1±21.9 °C
Index of Refraction: 1.529
Molar Refractivity: 137.0±0.3 cm3
#H bond acceptors: 3
#H bond donors: 3
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 1
ACD/LogP: 7.59
ACD/LogD (pH 5.5): 7.01
ACD/BCF (pH 5.5): 124219.05
ACD/KOC (pH 5.5): 154169.27
ACD/LogD (pH 7.4): 7.01
ACD/BCF (pH 7.4): 124219.05
ACD/KOC (pH 7.4): 154169.27
Polar Surface Area: 61 Å2
Polarizability: 54.3±0.5 10-24cm3
Surface Tension: 40.0±3.0 dyne/cm
Molar Volume: 444.5±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) =  7.43

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  521.50  (Adapted Stein & Brown method)
    Melting Pt (deg C):  222.64  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.89E-014  (Modified Grain method)
    Subcooled liquid VP: 3.76E-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):  0.0005767
       log Kow used: 7.43 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.34379 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.23E-007  atm-m3/mole
   Group Method:   5.23E-015  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  3.038E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  7.43  (KowWin est)
  Log Kaw used:  -4.670  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.100
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.0740
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.4403  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.6747  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3228
   Biowin6 (MITI Non-Linear Model):   0.0078
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.8311
 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):  5.01E-010 Pa (3.76E-012 mm Hg)
  Log Koa (Koawin est  ): 12.100
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.98E+003 
       Octanol/air (Koa) model:  0.309 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.961 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 140.5473 E-12 cm3/molecule-sec
      Half-Life =     0.076 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.913 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    43.000000 E-17 cm3/molecule-sec
      Half-Life =     0.027 Days (at 7E11 mol/cm3)
      Half-Life =     38.378 Min
   Reaction With Nitrate Radicals May Be Important!
   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    :  4.162E+005
      Log Koc:  5.619 

 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 = 4.222 (BCF = 1.669e+004)
       log Kow used: 7.43 (estimated)

 Volatilization from Water:
    Henry LC:  5.23E-007 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       2405  hours   (100.2 days)
    Half-Life from Model Lake : 2.642E+004  hours   (1101 days)

 Removal In Wastewater Treatment:
    Total removal:              93.96  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.19  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       0.00209         0.474        1000       
   Water     0.784           4.32e+003    1000       
   Soil      39.9            8.64e+003    1000       
   Sediment  59.4            3.89e+004    0          
     Persistence Time: 1.06e+004 hr

Click to predict properties on the Chemicalize site


Advertisement