ChemSpider 2D Image | Desonide | C24H32O6

Desonide

  • Molecular FormulaC24H32O6
  • Average mass416.507 Da
  • Monoisotopic mass416.219879 Da
  • ChemSpider ID4470603
  • defined stereocentres - 8 of 8 defined stereocentres


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Featured data source



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

(4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-5-Hydroxy-6b-(2-hydroxyacétyl)-4a,6a,8,8-tétraméthyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodécahydro-2H-naphto[2',1':4,5]indéno[1,2-d][1,3]dioxol-2-one [French] [ACD/IUPAC Name]
(4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-5-Hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-on
(4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
(4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-5-hydroxy-6b-(hydroxyacétyl)-4a,6a,8,8-tétraméthyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodécahydro-2H-naphto[2',1':4,5]indéno[1,2-d][1,3]dioxol-2-one
(4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-6b-Glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-on [German] [ACD/IUPAC Name]
(4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-6b-Glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one [ACD/IUPAC Name]
(4aR,4bS,6aS,6bS,9aR,10aS,10bS)-5-Hydroxy-6b-(2-hydroxyacétyl)-4a,6a,8,8-tétraméthyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodécahydro-2H-naphto[2',1':4,5]indéno[1,2-d][1,3]dioxol-2-one [French] [ACD/IUPAC Name]
(4aR,4bS,6aS,6bS,9aR,10aS,10bS)-6b-Glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-on [German] [ACD/IUPAC Name]
(4aR,4bS,6aS,6bS,9aR,10aS,10bS)-6b-Glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one [ACD/IUPAC Name]
11,21-Dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

D 2083 [DBID]
D03696 [DBID]
D-2083 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      D07AB08 Wikidata Q904011
      P261; P262 Biosynth Q-101382
      S01BA11 Wikidata Q904011
    • Chemical Class:

      Triamcinolone acetonide with hydrogen instead of the fluorine substituent at position 9. A corticosteroid anti-inflammatory, it is used topically as a cream, ointment or lotion for the treatment of va rious skin disorders. ChEBI CHEBI:204734
    • Bio Activity:

      Desonide is a nonfluorinated corticosteroid anti-inflammatory agent used topically for dermatoses. MedChem Express
      Desonide is a nonfluorinated corticosteroid anti-inflammatory agent used topically for dermatoses.; Target: Glucocorticoid Receptor; Desonide is a low-potency topical corticosteroid that has been used for decades in the treatment of steroid-responsive dermatoses [1]. MedChem Express HY-B0248
      Desonide is a nonfluorinated corticosteroid anti-inflammatory agent used topically for dermatoses.;Target: Glucocorticoid ReceptorDesonide is a low-potency topical corticosteroid that has been used for decades in the treatment of steroid-responsive dermatoses [1]. Desonide induced significant colorimetric improvement compared with placebo. A good to excellent response was achieved in 30% for desonide, and 6% for placebo. Decreased pigmentation in the desonide-treated axillae was associated with recovery of disruption at the basal membrane. Desonide showed depigmenting properties in women with axillary hyperpigmentation [2]. Given the favorable safety profile of all other desonide preparations and their utility as a low potency corticosteroid, desonide foam promises to be a useful addition to the armamentarium, when other desonide vehicles might be less acceptable [3]. MedChem Express HY-B0248
      Glucocorticoid Receptor MedChem Express HY-B0248
      GPCR/G protein MedChem Express HY-B0248
      GPCR/G protein; MedChem Express HY-B0248

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

Density: 1.3±0.1 g/cm3
Boiling Point: 580.1±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.7 mmHg at 25°C
Enthalpy of Vaporization: 99.6±6.0 kJ/mol
Flash Point: 196.9±23.6 °C
Index of Refraction: 1.598
Molar Refractivity: 109.3±0.4 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 2.62
ACD/LogD (pH 5.5): 2.80
ACD/BCF (pH 5.5): 78.37
ACD/KOC (pH 5.5): 789.67
ACD/LogD (pH 7.4): 2.80
ACD/BCF (pH 7.4): 78.37
ACD/KOC (pH 7.4): 789.67
Polar Surface Area: 93 Å2
Polarizability: 43.3±0.5 10-24cm3
Surface Tension: 55.9±5.0 dyne/cm
Molar Volume: 320.1±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) =  4.16

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  528.16  (Adapted Stein & Brown method)
    Melting Pt (deg C):  225.75  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.37E-014  (Modified Grain method)
    MP  (exp database):  274 deg C
    Subcooled liquid VP: 7.6E-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):  0.6818
       log Kow used: 4.16 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.26872 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.94E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.101E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.16  (KowWin est)
  Log Kaw used:  -10.695  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.855
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.5501
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.6879  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.8280  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5149
   Biowin6 (MITI Non-Linear Model):   0.0279
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.3293
 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):  1.01E-009 Pa (7.6E-012 mm Hg)
  Log Koa (Koawin est  ): 14.855
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.96E+003 
       Octanol/air (Koa) model:  176 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  93.6478 E-12 cm3/molecule-sec
      Half-Life =     0.114 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.371 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.312500 E-17 cm3/molecule-sec
      Half-Life =     0.873 Days (at 7E11 mol/cm3)
      Half-Life =     20.955 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    :  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 = 2.501 (BCF = 316.7)
       log Kow used: 4.16 (estimated)

 Volatilization from Water:
    Henry LC:  4.94E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.419E+009  hours   (1.008E+008 days)
    Half-Life from Model Lake : 2.639E+010  hours   (1.099E+009 days)

 Removal In Wastewater Treatment:
    Total removal:              37.86  percent
    Total biodegradation:        0.38  percent
    Total sludge adsorption:    37.48  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       0.0202          2.42         1000       
   Water     5.88            4.32e+003    1000       
   Soil      90.3            8.64e+003    1000       
   Sediment  3.83            3.89e+004    0          
     Persistence Time: 4.95e+003 hr




                    

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