ChemSpider 2D Image | 4beta-Phorbol | C20H28O6

4β-Phorbol

  • Molecular FormulaC20H28O6
  • Average mass364.433 Da
  • Monoisotopic mass364.188599 Da
  • ChemSpider ID390610

  • defined stereocentres - 8 of 8 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

4β-Phorbol
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-Tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulen-5-on [German] [ACD/IUPAC Name]
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-Tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulen-5-one [ACD/IUPAC Name]
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-Tétrahydroxy-3-(hydroxyméthyl)-1,1,6,8-tétraméthyl-1,1a,1b,4,4a,7a,7b,8,9,9a-décahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulén-5-one [French] [ACD/IUPAC Name]
17673-25-5 [RN]
5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one, 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)- [ACD/Index Name]
Phorbol [Wiki]
TPA
XUZ76S9127
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5H-cyclopropa[3,4]benz[1,2-e]azulen-5-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

HSDB 4328 [DBID]
AIDS001981 [DBID]
AIDS-001981 [DBID]
C09155 [DBID]
CCRIS 694 [DBID]
CHEBI:8116 [DBID]
NSC 154778 [DBID]
NSC154778 [DBID]
P8893_SIGMA [DBID]
  • Miscellaneous

    • Toxicity:

      Organic Compound; Ester; Plant Toxin; Industrial/Workplace Toxin; Natural Compound Toxin, Toxin-Target Database T3D4069

    • Chemical Class:

      A diterpenoid with the structure of tigliane hydroxylated at C-4, -9, -12(<stereo>beta</stereo>), -13 and -20, with an oxo group at C-3 and unsaturation at the 1- and 6-positions. ChEBI CHEBI:8116
      A diterpenoid with the structure of tigliane hydroxylated at C-4, -9, -12(beta), -13 and -20, with an oxo group at C-3 and unsaturation at the 1- and 6-positions. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8116, CHEBI:8116

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

Density: 1.4±0.1 g/cm3
Boiling Point: 572.0±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.6 mmHg at 25°C
Enthalpy of Vaporization: 98.5±6.0 kJ/mol
Flash Point: 313.8±26.6 °C
Index of Refraction: 1.648
Molar Refractivity: 93.7±0.3 cm3
#H bond acceptors: 6
#H bond donors: 5
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 1
ACD/LogP: 0.42
ACD/LogD (pH 5.5): 0.99
ACD/BCF (pH 5.5): 3.35
ACD/KOC (pH 5.5): 82.70
ACD/LogD (pH 7.4): 0.99
ACD/BCF (pH 7.4): 3.35
ACD/KOC (pH 7.4): 82.69
Polar Surface Area: 118 Å2
Polarizability: 37.1±0.5 10-24cm3
Surface Tension: 70.6±3.0 dyne/cm
Molar Volume: 257.4±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) =  -0.54

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  523.99  (Adapted Stein & Brown method)
    Melting Pt (deg C):  223.81  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.14E-014  (Modified Grain method)
    MP  (exp database):  249 dec deg C
    Subcooled liquid VP: 3.11E-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):  1.479e+004
       log Kow used: -0.54 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  11724 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 :   3.71E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.696E-019 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.54  (KowWin est)
  Log Kaw used:  -8.819  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.279
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1626
   Biowin2 (Non-Linear Model)     :   0.0007
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8428  (months      )
   Biowin4 (Primary Survey Model) :   2.9449  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4838
   Biowin6 (MITI Non-Linear Model):   0.0322
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.9893
 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):  4.15E-010 Pa (3.11E-012 mm Hg)
  Log Koa (Koawin est  ): 8.279
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.23E+003 
       Octanol/air (Koa) model:  4.67E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.00372 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 241.8546 E-12 cm3/molecule-sec
      Half-Life =     0.044 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.531 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
   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    :  450.1
      Log Koc:  2.653 

 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: -0.54 (estimated)

 Volatilization from Water:
    Henry LC:  3.71E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.013E+007  hours   (1.255E+006 days)
    Half-Life from Model Lake : 3.287E+008  hours   (1.369E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       0.0236          0.36         1000       
   Water     55.8            1.44e+003    1000       
   Soil      44              2.88e+003    1000       
   Sediment  0.109           1.3e+004     0          
     Persistence Time: 720 hr

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