ChemSpider 2D Image | Ecdysone | C27H44O6

Ecdysone

  • Molecular FormulaC27H44O6
  • Average mass464.635 Da
  • Monoisotopic mass464.313782 Da
  • ChemSpider ID18130
  • defined stereocentres - 10 of 10 defined stereocentres


More details:



Featured data source



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

(2b,3b,5b,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-one
(2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-Dihydroxy-6-methyl-2-heptanyl]-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-on [German]
(2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-Dihydroxy-6-methyl-2-heptanyl]-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
(2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-Dihydroxy-6-méthyl-2-heptanyl]-2,3,14-trihydroxy-10,13-diméthyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tétradécahydro-6H-cyclopenta[a]phénanthrén-6-one [French]
(2β,3β,5β,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-on [German] [ACD/IUPAC Name]
(2β,3β,5β,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-one [ACD/IUPAC Name]
(2β,3β,5β,22R)-2,3,14,22,25-Pentahydroxycholest-7-én-6-one [French] [ACD/IUPAC Name]
222-760-4 [EINECS]
2422986
2β,3β,14α,22(R),25-Pentahydroxy-7-cholesten-6-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AI3-44726 [DBID]
BRN 2422986 [DBID]
C00477 [DBID]
CCRIS 6931 [DBID]
CHEBI:16688 [DBID]
E9004_SIGMA [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      Xn Abblis Chemicals AB1009360
    • Chemical Class:

      A 6-oxo steroid that is 5<stereo>beta</stereo>-cholest-7-en-6-one substituted by hydroxy groups at positions 2, 3, 14, 22 and 25 respectively (the 2<stereo>beta</stereo>, 3<stereo>beta</stereo>, 22<st ereo>R</stereo> stereoisomer). It is a steroid prohormone of the major insect moulting hormone 20-hydroxyecdysone. ChEBI CHEBI:16688
      A 6-oxo steroid that is 5beta-cholest-7-en-6-one substituted by hydroxy groups at positions 2, 3, 14, 22 and 25 respectively (the 2beta, 3beta, 22R stereoisomer). It is a steroid prohormone of the maj or insect moulting hormone 20-hydroxyecdysone. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16688
    • Bio Activity:

      Biochemicals & small molecules/Agonists & activators Hello Bio [HB3881]
      Ecdysone receptor (EcR) agonist Hello Bio [HB3881]
      Receptors & Transporters/Nuclear hormone/Other/Ecdysone receptor Hello Bio [HB3881]
      Steroidal prohormone of the major insect molting hormone 20-hydroxyecdysone. A member of the ecdysteroid family. Ecdysone receptor (EcR) agonist. Induces the expression of genes coding for proteins that the larva requires, and it causes chromosome puffs (sites of high expression) to form in polytene chromosomes. Plays a key role in insect development, cell proliferaton, growth and apoptosis by controlling gene expression involved in moulting and metamorphosis. It acts through a heterodimeric receptor comprising the ecdysone receptor and the ultraspiracle proteins (USP). Appears in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects. Used for controlled gene expression in scientific research, agriculture and medicine. Used for the development of selective insect growth regulators for use as environmentally benign insecticides. Hello Bio [HB3881]

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

Density: 1.2±0.1 g/cm3
Boiling Point: 632.0±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.2 mmHg at 25°C
Enthalpy of Vaporization: 107.1±6.0 kJ/mol
Flash Point: 350.0±28.0 °C
Index of Refraction: 1.582
Molar Refractivity: 126.2±0.4 cm3
#H bond acceptors: 6
#H bond donors: 5
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: 0.87
ACD/LogD (pH 5.5): 1.40
ACD/BCF (pH 5.5): 6.88
ACD/KOC (pH 5.5): 138.44
ACD/LogD (pH 7.4): 1.40
ACD/BCF (pH 7.4): 6.88
ACD/KOC (pH 7.4): 138.44
Polar Surface Area: 118 Å2
Polarizability: 50.0±0.5 10-24cm3
Surface Tension: 56.9±5.0 dyne/cm
Molar Volume: 378.2±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) =  2.01

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  592.39  (Adapted Stein & Brown method)
    Melting Pt (deg C):  255.76  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.79E-017  (Modified Grain method)
    Subcooled liquid VP: 1.58E-014 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):  23.26
       log Kow used: 2.01 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  15713 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 :   6.08E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.259E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.01  (KowWin est)
  Log Kaw used:  -11.605  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.615
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2736
   Biowin2 (Non-Linear Model)     :   0.0005
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7813  (months      )
   Biowin4 (Primary Survey Model) :   2.9297  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3878
   Biowin6 (MITI Non-Linear Model):   0.0200
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.7684
 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):  2.11E-012 Pa (1.58E-014 mm Hg)
  Log Koa (Koawin est  ): 13.615
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.42E+006 
       Octanol/air (Koa) model:  10.1 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 139.8414 E-12 cm3/molecule-sec
      Half-Life =     0.076 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.918 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   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    :  2.434E+004
      Log Koc:  4.386 

 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 = 0.845 (BCF = 7.003)
       log Kow used: 2.01 (estimated)

 Volatilization from Water:
    Henry LC:  6.08E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.076E+010  hours   (8.649E+008 days)
    Half-Life from Model Lake : 2.264E+011  hours   (9.435E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               2.25  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.16  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       0.0647          1.71         1000       
   Water     28.8            1.44e+003    1000       
   Soil      71              2.88e+003    1000       
   Sediment  0.115           1.3e+004     0          
     Persistence Time: 1.15e+003 hr




                    

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