ChemSpider 2D Image | Ecdysterone | C27H44O7

Ecdysterone

  • Molecular FormulaC27H44O7
  • Average mass480.634 Da
  • Monoisotopic mass480.308716 Da
  • ChemSpider ID4573597

  • defined stereocentres - 10 of 10 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(1S,3aS,5aR,7R,8S,9aR,9bR,11aR)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1H,2H,3H,3aH,5H,5aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-5-one
(2b,3b,5b,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-Trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methyl-2-heptanyl]-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-on
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-Trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methyl-2-heptanyl]-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,17S)-2,3,14-Trihydroxy-10,13-diméthyl-17-[(2R,3R)-2,3,6-trihydroxy-6-méthyl-2-heptanyl]-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)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-on [German] [ACD/IUPAC Name]
(2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one [ACD/IUPAC Name]
(2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-én-6-one [French] [ACD/IUPAC Name]
20-hydroxy Ecdysone
20-hydroxyecdysone
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

779A7KPL0Y [DBID]
AI3-44727 [DBID]
AIDS013374 [DBID]
AIDS-013374 [DBID]
BRN 1917578 [DBID]
CHEBI:16587 [DBID]
H5142_SIGMA [DBID]
NSC629484 [DBID]
PubChem Substance ID 24856928 [DBID]
UNII:779A7KPL0Y [DBID]
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  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Target Organs:

      Others TargetMol T2881

    • Chemical Class:

      An ecdysteroid that is ecdysone substituted by a hydroxy group at position 20. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16587, CHEBI:16587

    • Bio Activity:

      A member of the ecdysteroid family. Ecdysone receptor (EcR) agonist. More potent than ecdysone. 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). Regulates lipolysis in insects. 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. Shows biological effects on mammalian species. Neurosteroid. Antiepileptic. Acts on the modulatory site of the GABAA receptor and potentiates GABAergic inhibition in rat. Was shown to stimulate and modulate neutrophil production. Antidiabetic and antiobesity. Could be used as a nutritional supplement for the prevention and treatment of obesity and obesity-associated disorders. May protect PC12 cells against CoCl(2)-induced cell injury by inhibiting ROS production and modulating components of the mitochondrial apoptosis pathway. Does not have potent anabolic properties, however, a muscle-specific increase is observed and genes are identified to provide an explanation for the muscle accretion. Potential fibrosis antagonist for renal proximal tubule cells. Acts through suppressing post-receptor signaling of TGF-beta1 and blocking the expression of Snail. Hello Bio HB3718
      Biochemicals & small molecules/Agonists & activators Hello Bio HB3718
      Ecdysone receptor (EcR) agonist. More potent than Ecdysone. Hello Bio HB3718
      Others TargetMol T2881
      Receptors & Transporters/Nuclear hormone/Other/Ecdysone receptor Hello Bio HB3718

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

Density: 1.3±0.1 g/cm3
Boiling Point: 702.1±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±5.0 mmHg at 25°C
Enthalpy of Vaporization: 117.5±6.0 kJ/mol
Flash Point: 392.4±29.4 °C
Index of Refraction: 1.597
Molar Refractivity: 127.8±0.4 cm3
#H bond acceptors: 7
#H bond donors: 6
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: -0.53
ACD/LogD (pH 5.5): 0.63
ACD/BCF (pH 5.5): 1.76
ACD/KOC (pH 5.5): 52.26
ACD/LogD (pH 7.4): 0.63
ACD/BCF (pH 7.4): 1.76
ACD/KOC (pH 7.4): 52.26
Polar Surface Area: 138 Å2
Polarizability: 50.7±0.5 10-24cm3
Surface Tension: 62.3±5.0 dyne/cm
Molar Volume: 375.2±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) =  0.50

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  622.07  (Adapted Stein & Brown method)
    Melting Pt (deg C):  269.62  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.15E-018  (Modified Grain method)
    Subcooled liquid VP: 1.54E-015 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):  353.1
       log Kow used: 0.50 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5.7993e+005 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 :   2.22E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.642E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.50  (KowWin est)
  Log Kaw used:  -13.042  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.542
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.0821
   Biowin2 (Non-Linear Model)     :   0.0001
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5338  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.7532  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4584
   Biowin6 (MITI Non-Linear Model):   0.0208
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.9367
 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):  2.05E-013 Pa (1.54E-015 mm Hg)
  Log Koa (Koawin est  ): 13.542
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.46E+007 
       Octanol/air (Koa) model:  8.55 
   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 = 163.6873 E-12 cm3/molecule-sec
      Half-Life =     0.065 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.784 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    :  3.661E+004
      Log Koc:  4.564 

 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: 0.50 (estimated)

 Volatilization from Water:
    Henry LC:  2.22E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.782E+011  hours   (2.409E+010 days)
    Half-Life from Model Lake : 6.308E+012  hours   (2.628E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       0.0661          1.47         1000       
   Water     57.1            4.32e+003    1000       
   Soil      42.7            8.64e+003    1000       
   Sediment  0.116           3.89e+004    0          
     Persistence Time: 985 hr

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