ChemSpider 2D Image | Triamcinolone acetonide | C24H31FO6

Triamcinolone acetonide

  • Molecular FormulaC24H31FO6
  • Average mass434.498 Da
  • Monoisotopic mass434.210480 Da
  • ChemSpider ID6196
  • defined stereocentres - 8 of 8 defined stereocentres


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Triamcinolone acetonide [JAN] [Wiki]
(11b,16a)-9-Fluoro-11,21-dihydroxy-16,17-[1-methylethylidenebis(oxy)]pregna-1,4-diene-3,20-dione
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-Fluor-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
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-Fluor-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]
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-Fluoro-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]
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-fluoro-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
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-fluoro-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
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-Fluoro-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]
2H-Naphth[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one, 4b-fluoro-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-5-hydroxy-6b-(2-hydroxyacetyl)-4a,6a,8,8-tetramethyl-, (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)- [ACD/Index Name]
2H-naphth[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one, 4b-fluoro-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-, (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BRN 0060069 [DBID]
C08183 [DBID]
CCRIS 5231 [DBID]
D00983 [DBID]
MLS000028538 [DBID]
NSC 21916 [DBID]
NSC21916 [DBID]
SMR000058335 [DBID]
T6501_SIGMA [DBID]
ZINC03875481 [DBID]

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

Density: 1.3±0.1 g/cm3
Boiling Point: 576.9±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.6 mmHg at 25°C
Enthalpy of Vaporization: 99.2±6.0 kJ/mol
Flash Point: 302.7±30.1 °C
Index of Refraction: 1.589
Molar Refractivity: 109.4±0.4 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 2.50
ACD/LogD (pH 5.5): 2.57
ACD/BCF (pH 5.5): 53.25
ACD/KOC (pH 5.5): 598.86
ACD/LogD (pH 7.4): 2.57
ACD/BCF (pH 7.4): 53.25
ACD/KOC (pH 7.4): 598.85
Polar Surface Area: 93 Å2
Polarizability: 43.4±0.5 10-24cm3
Surface Tension: 54.6±5.0 dyne/cm
Molar Volume: 324.8±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) =  2.69
    Log Kow (Exper. database match) =  2.53
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  523.17  (Adapted Stein & Brown method)
    Melting Pt (deg C):  223.42  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.15E-014  (Modified Grain method)
    MP  (exp database):  293 deg C
    Subcooled liquid VP: 1.1E-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):  12.89
       log Kow used: 2.53 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  21 mg/L (28 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  21.391 mg/L
    Wat Sol (Exper. database match) =  21.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.83E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.101E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.53  (exp database)
  Log Kaw used:  -10.396  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.926
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.7426
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.4360  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.6486  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5339
   Biowin6 (MITI Non-Linear Model):   0.0005
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.7029
 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):  1.47E-009 Pa (1.1E-011 mm Hg)
  Log Koa (Koawin est  ): 12.926
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.05E+003 
       Octanol/air (Koa) model:  2.07 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.994 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  87.4418 E-12 cm3/molecule-sec
      Half-Life =     0.122 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.468 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 = 1.248 (BCF = 17.71)
       log Kow used: 2.53 (expkow database)

 Volatilization from Water:
    Henry LC:  9.83E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.242E+009  hours   (5.173E+007 days)
    Half-Life from Model Lake : 1.354E+010  hours   (5.643E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               3.18  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     3.08  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       0.037           2.57         1000       
   Water     15.1            4.32e+003    1000       
   Soil      84.7            8.64e+003    1000       
   Sediment  0.145           3.89e+004    0          
     Persistence Time: 2.89e+003 hr




                    

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