ChemSpider 2D Image | Triptolide | C20H24O6

Triptolide

  • Molecular FormulaC20H24O6
  • Average mass360.401 Da
  • Monoisotopic mass360.157288 Da
  • ChemSpider ID97099
  • defined stereocentres - 9 of 9 defined stereocentres


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Featured data source



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

(3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-6-Hydroxy-6a-isopropyl-8b-methyl-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydrotrisoxireno[6,7:8a,9:4b,5]phenanthro[1,2-c]furan-1(3H)-on [German] [ACD/IUPAC Name]
(3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-6-Hydroxy-6a-isopropyl-8b-methyl-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydrotrisoxireno[6,7:8a,9:4b,5]phenanthro[1,2-c]furan-1(3H)-one [ACD/IUPAC Name]
(3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-6-Hydroxy-6a-isopropyl-8b-méthyl-3b,4,4a,6,6a,7a,7b,8b,9,10-décahydrotrisoxiréno[6,7:8a,9:4b,5]phénanthro[1,2-c]furan-1(3H)-one [French] [ACD/IUPAC Name]
(3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-6-hydroxy-8b-methyl-6a-(propan-2-yl)-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydrotrisoxireno[6,7:8a,9:4b,5]phenanthro[1,2-c]furan-1(3H)-one
19ALD1S53J
38748-32-2 [RN]
Triptolide [Wiki]
Trisoxireno[6,7:8a,9:4b,5]phenanthro[1,2-c]furan-1(3H)-one, 3b,4,4a,6,6a,7a,7b,8b,9,10-decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)-, (3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)- [ACD/Index Name]
(1S,2S,4S,5S,7R,8R,9S,11S,13S)-8-hydroxy-1-methyl-7-(propan-2-yl)-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one
(3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-3b,4,4a,6,6a,7a,7b,8b,9,10-Decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)trisoxireno[4b,5:6,7:8a,9]phenanthro[1,2-c]furan-1(3H)-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Bio2_000315 [DBID]
Bio2_000795 [DBID]
C09204 [DBID]
KBio2_000315 [DBID]
KBio2_002883 [DBID]
KBio2_005451 [DBID]
KBio3_000629 [DBID]
KBio3_000630 [DBID]
KBioGR_000315 [DBID]
KBioSS_000315 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      P261; P262 Biosynth Q-100450
    • Target Organs:

      Others TargetMol T2179
    • Bio Activity:

      Enzymes Tocris Bioscience 3253
      Inhibits DNA-dependent ATPase activity of XBP and induces inhibition of RNA polymerase II (RNAPII)-mediated transcription (IC50 = 200 nM). Selective for RNAPII over RNAPI and RNAPIII. Blocks RNA synth esis in HeLa cells (IC50 = 62 nM); exhibits potent antiproliferative activity in 60 cancer cell lines (average IC50 = 12 nM) and induces apoptosis by blocking TNF-?-mediated c-IAP1 and c-IAP2 inductio n. Also displays immunosuppressive and anti-inflammatory activity. Tocris Bioscience 3253
      Inhibits DNA-dependent ATPase activity of XBP and induces inhibition of RNA polymerase II (RNAPII)-mediated transcription (IC50 = 200 nM). Selective for RNAPII over RNAPI and RNAPIII. Blocks RNA synthesis in HeLa cells (IC50 = 62 nM); exhibits potent antiproliferative activity in 60 cancer cell lines (average IC50 = 12 nM) and induces apoptosis by blocking TNF-?-mediated c-IAP1 and c-IAP2 induction. Also displays immunosuppressive and anti-inflammatory activity. Tocris Bioscience 3253
      Inhibits DNA-dependent ATPase activity of XBP and induces inhibition of RNA polymerase II (RNAPII)-mediated transcription (IC50 = 200 nM). Selective for RNAPII over RNAPI and RNAPIII. Blocks RNA synthesis in HeLa cells (IC50 = 62 nM); exhibits potent antiproliferative activity in 60 cancer cell lines (average IC50 = 12 nM) and induces apoptosis by blocking TNF-alpha-mediated c-IAP1 and c-IAP2 induction. Also displays immunosuppressive and anti-inflammatory activity. Tocris Bioscience 3253
      Inhibits RNAPII-mediated transcription; antitumor, anti-inflammatory and immunosuppressive Tocris Bioscience 3253
      Others TargetMol T2179
      Polymerases Tocris Bioscience 3253
      RNA/DNA Polymerase Tocris Bioscience 3253

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

Density: 1.5±0.1 g/cm3
Boiling Point: 601.7±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.9 mmHg at 25°C
Enthalpy of Vaporization: 102.7±6.0 kJ/mol
Flash Point: 220.7±25.0 °C
Index of Refraction: 1.647
Molar Refractivity: 88.3±0.4 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 1.27
ACD/LogD (pH 5.5): 0.67
ACD/BCF (pH 5.5): 1.91
ACD/KOC (pH 5.5): 55.28
ACD/LogD (pH 7.4): 0.67
ACD/BCF (pH 7.4): 1.91
ACD/KOC (pH 7.4): 55.28
Polar Surface Area: 84 Å2
Polarizability: 35.0±0.5 10-24cm3
Surface Tension: 61.8±5.0 dyne/cm
Molar Volume: 243.0±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) =  0.99

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  461.31  (Adapted Stein & Brown method)
    Melting Pt (deg C):  194.53  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.6E-011  (Modified Grain method)
    Subcooled liquid VP: 2.78E-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):  2493
       log Kow used: 0.99 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2041.3 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.63E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.750E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.99  (KowWin est)
  Log Kaw used:  -13.829  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.819
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.8689
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8284  (months      )
   Biowin4 (Primary Survey Model) :   3.0432  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5114
   Biowin6 (MITI Non-Linear Model):   0.0523
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.6553
 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):  3.71E-007 Pa (2.78E-009 mm Hg)
  Log Koa (Koawin est  ): 14.819
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  8.09 
       Octanol/air (Koa) model:  162 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.997 
       Mackay model           :  0.998 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 140.0324 E-12 cm3/molecule-sec
      Half-Life =     0.076 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.917 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    48.059372 E-17 cm3/molecule-sec
      Half-Life =     0.024 Days (at 7E11 mol/cm3)
      Half-Life =     34.337 Min
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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: 0.99 (estimated)

 Volatilization from Water:
    Henry LC:  3.63E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.062E+012  hours   (1.276E+011 days)
    Half-Life from Model Lake :  3.34E+013  hours   (1.392E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               1.89  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.79  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       1.59e-006       0.436        1000       
   Water     43.4            1.44e+003    1000       
   Soil      56.6            2.88e+003    1000       
   Sediment  0.0926          1.3e+004     0          
     Persistence Time: 1.28e+003 hr




                    

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