ChemSpider 2D Image | (+)-Ingenol | C20H28O5

(+)-Ingenol

  • Molecular FormulaC20H28O5
  • Average mass348.433 Da
  • Monoisotopic mass348.193665 Da
  • ChemSpider ID10282511
  • defined stereocentres - 8 of 8 defined stereocentres


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(+)-Ingenol
(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-1a,2,5,5a,6,9,10,10a-Octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one
(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one
(1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-Trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-on [German] [ACD/IUPAC Name]
(1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-Trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one [ACD/IUPAC Name]
(1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-Trihydroxy-7-(hydroxyméthyl)-3,11,11,14-tétraméthyltétracyclo[7.5.1.01,5.010,12]pentadéca-2,7-dién-15-one [French] [ACD/IUPAC Name]
1aa,2a,5b,5ab,6b,8ab,9a,10,10aa-Octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one
1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one, 1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-, (1aR,2S,5R,5aR,6S,8aS,9R,10aR)- [ACD/Index Name]
30220-46-3 [RN]
IC77UZI9G8
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A tetracyclic diterpenoid that is 1a,2,5,5a,6,9,10,10a-octahydro-1<element>H</element>-2,8a-methanocyclopenta[<ital>a</ital>]cyclopropa[<ital>e</ital>][10]annulen-11-one substituted at positions 5, 5a and 6 by hydroxy groups, positions 1, 1, 7 and 9 by methyl groups, position 4 by a hydroxymethyl group and position 1 by an oxo group (the 1a<stereo>R</stereo>,2<stereo>S</stereo>,5<stereo>R</stereo> ,5a<stereo>R</stereo>,6<stereo>S</stereo>,8a<stereo>S</stereo>,9<stereo>R</stereo>,10a<stereo>R</stereo> diastereomer). ChEBI CHEBI:5922
      A tetracyclic diterpenoid that is 1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one substituted at positions 5, 5a; and 6 by hydroxy groups, positions 1, 1, 7 and 9 by methyl groups, position 4 by a hydroxymethyl group and position 1 by an oxo group (the 1aR,2S,5R; ,5aR,6S,8aS,9R,10aR diastereomer). ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5922
    • Bio Activity:

      Ingenol is an extremely weak PKC (protein kinase C) activator; has been found to induce apoptosis and act as an anticancer agent. MedChem Express http://www.medchemexpress.com/20-Deoxyingenol.html, HY-N0865
      Ingenol is an extremely weak PKC (protein kinase C) activator; has been found to induce apoptosis and act as an anticancer agent. ;IC50 value:;Target: anticancer natural compound;In vitro: ingenol indeed binds to protein kinase C with a Ki of 30 microM and activates the enzyme. In addition, ingenol was biologically active in 3 separate cell systems, showing effects similar to the phorbol esters on morphological change, cell-cell communication, epidermal growth factor binding, arachidonic acid metabolite release, and ornithine decarboxylase activity [1]. MedChem Express HY-N0865
      Others MedChem Express HY-N0865

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

Density: 1.3±0.1 g/cm3
Boiling Point: 523.8±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.1 mmHg at 25°C
Enthalpy of Vaporization: 91.8±6.0 kJ/mol
Flash Point: 284.7±26.6 °C
Index of Refraction: 1.625
Molar Refractivity: 92.0±0.4 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 2.95
ACD/LogD (pH 5.5): 2.93
ACD/BCF (pH 5.5): 99.59
ACD/KOC (pH 5.5): 937.42
ACD/LogD (pH 7.4): 2.93
ACD/BCF (pH 7.4): 99.59
ACD/KOC (pH 7.4): 937.40
Polar Surface Area: 98 Å2
Polarizability: 36.5±0.5 10-24cm3
Surface Tension: 62.4±5.0 dyne/cm
Molar Volume: 260.1±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) =  1.39

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  501.25  (Adapted Stein & Brown method)
    Melting Pt (deg C):  213.18  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.75E-013  (Modified Grain method)
    Subcooled liquid VP: 1.76E-011 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):  410
       log Kow used: 1.39 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  54758 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.46E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.957E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.39  (KowWin est)
  Log Kaw used:  -10.739  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.129
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5129
   Biowin2 (Non-Linear Model)     :   0.0147
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2502  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2508  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6374
   Biowin6 (MITI Non-Linear Model):   0.0782
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4829
 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):  2.35E-009 Pa (1.76E-011 mm Hg)
  Log Koa (Koawin est  ): 12.129
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.28E+003 
       Octanol/air (Koa) model:  0.33 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.964 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 233.3921 E-12 cm3/molecule-sec
      Half-Life =     0.046 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.550 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    50.393749 E-17 cm3/molecule-sec
      Half-Life =     0.023 Days (at 7E11 mol/cm3)
      Half-Life =     32.747 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    :  299.3
      Log Koc:  2.476 

 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 = 0.372 (BCF = 2.354)
       log Kow used: 1.39 (estimated)

 Volatilization from Water:
    Henry LC:  4.46E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  2.45E+009  hours   (1.021E+008 days)
    Half-Life from Model Lake : 2.673E+010  hours   (1.114E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               1.94  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.85  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       0.0233          0.365        1000       
   Water     41.8            900          1000       
   Soil      58.1            1.8e+003     1000       
   Sediment  0.0999          8.1e+003     0          
     Persistence Time: 710 hr




                    

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