ChemSpider 2D Image | (−)-Epothilone A | C26H39NO6S

(−)-Epothilone A

  • Molecular FormulaC26H39NO6S
  • Average mass493.656 Da
  • Monoisotopic mass493.249817 Da
  • ChemSpider ID395491

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 7 of 7 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(−)-Epothilone A
(-)-Epothilone A
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)-1-propen-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecan-5,9-dion [German] [ACD/IUPAC Name]
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)-1-propen-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione [ACD/IUPAC Name]
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12-tétraméthyl-3-[(1E)-1-(2-méthyl-1,3-thiazol-4-yl)-1-propén-2-yl]-4,17-dioxabicyclo[14.1.0]heptadécane-5,9-dione [French] [ACD/IUPAC Name]
(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
152044-53-6 [RN]
4,17-Dioxabicyclo[14.1.0]heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (1S,3S,7S,10R,11S,12S,16R)- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C12153 [DBID]
E3656_SIGMA [DBID]
nchembio853-comp5 [DBID]
NCI60_030304 [DBID]
NSC684362 [DBID]
  • Miscellaneous

    • Chemical Class:

      An epithilone that is epothilone C in which the double bond in the macrocyclic lactone ring has been oxidised to the corresponding epoxide (the 13<stereo>R</stereo>,14<stereo>S</stereo> diastereoisome r). ChEBI CHEBI:31549
      An epithilone that is epothilone C in which the double bond in the macrocyclic lactone ring has been oxidised to the corresponding epoxide (the 13R,14S diastereoisomer). ChEBI CHEBI:31549

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

Density: 1.1±0.1 g/cm3
Boiling Point: 683.3±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 105.3±3.0 kJ/mol
Flash Point: 367.1±31.5 °C
Index of Refraction: 1.532
Molar Refractivity: 133.8±0.3 cm3
#H bond acceptors: 7
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 2.54
ACD/LogD (pH 5.5): 2.94
ACD/BCF (pH 5.5): 100.91
ACD/KOC (pH 5.5): 946.00
ACD/LogD (pH 7.4): 2.94
ACD/BCF (pH 7.4): 101.03
ACD/KOC (pH 7.4): 947.08
Polar Surface Area: 137 Å2
Polarizability: 53.0±0.5 10-24cm3
Surface Tension: 41.5±3.0 dyne/cm
Molar Volume: 431.8±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) =  4.12

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  650.07  (Adapted Stein & Brown method)
    Melting Pt (deg C):  282.70  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.12E-018  (Modified Grain method)
    Subcooled liquid VP: 7.98E-016 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):  0.2381
       log Kow used: 4.12 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  199.79 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Epoxides
       Esters

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.27E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.055E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.12  (KowWin est)
  Log Kaw used:  -16.874  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.994
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5344
   Biowin2 (Non-Linear Model)     :   0.0621
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2503  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3694  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3400
   Biowin6 (MITI Non-Linear Model):   0.0049
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.9724
 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):  1.06E-013 Pa (7.98E-016 mm Hg)
  Log Koa (Koawin est  ): 20.994
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.82E+007 
       Octanol/air (Koa) model:  2.42E+008 
   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 = 171.2343 E-12 cm3/molecule-sec
      Half-Life =     0.062 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.750 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    88.724998 E-17 cm3/molecule-sec
      Half-Life =     0.013 Days (at 7E11 mol/cm3)
      Half-Life =     18.599 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    :  164.2
      Log Koc:  2.215 

 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 = 2.473 (BCF = 297)
       log Kow used: 4.12 (estimated)

 Volatilization from Water:
    Henry LC:  3.27E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.978E+015  hours   (1.658E+014 days)
    Half-Life from Model Lake :  4.34E+016  hours   (1.808E+015 days)

 Removal In Wastewater Treatment:
    Total removal:              35.83  percent
    Total biodegradation:        0.37  percent
    Total sludge adsorption:    35.46  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       0.00358         0.257        1000       
   Water     12.7            900          1000       
   Soil      83.3            1.8e+003     1000       
   Sediment  3.97            8.1e+003     0          
     Persistence Time: 1.55e+003 hr

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