(1aR,2R,3R,3aR,7bS)-3,3',3',3a-Tetramethyl-6-oxo-2,3,3a,4,6,7b-hexahydro-1aH-spiro[naphtho[1,2-b]oxirene-5,2'-oxiran]-2-yl acetate

Molecular FormulaC₁₇H₂₂O₅
Average mass306.354 Da
Monoisotopic mass306.146729 Da
ChemSpider ID151736

- 5 of 6 defined stereocentres

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Names and Synonyms

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

(1aR,2R,3R,3aR,7bS)-3,3',3',3a-Tetramethyl-6-oxo-2,3,3a,4,6,7b-hexahydro-1aH-spiro[naphtho[1,2-b]oxirene-5,2'-oxiran]-2-yl acetate [ACD/IUPAC Name]

Spiro[naphth[1,2-b]oxirene-5(6H),2'-oxiran]-6-one, 2-(acetyloxy)-1a,2,3,3a,4,7b-hexahydro-3,3',3',3a-tetramethyl-, (1aR,2R,3R,3aR,7bS)- [ACD/Index Name]

(1aR,2R,3R,3aR,7bS)-3,3a,3',3'-tetramethyl-6-oxo-2,3,3a,4,6,7b-hexahydro-1aH-spiro[naphtho[1,2-b]oxirene-5,2'-oxiran]-2-yl acetate

(1aR,5R)-2α-Acetoxy-1aβ,2,3,3a,4,7bβ-hexahydro-3α,3',3',3aα-tetramethylspiro[naphth[1,2-b]oxirene-5(6H),2'-oxiran]-6-one

[(1Ar,2R,3R,3aR,7bS)-3,3',3',3a-tetramethyl-6-oxospiro[2,3,4,7b-tetrahydro-1aH-naphtho[1,2-b]oxirene-5,2'-oxirane]-2-yl] acetate

62445-06-1 [RN]

Eremofortin A

Spiro(naphth(1,2-b)oxirene-5(6H),2'-oxiran)-6-one, 2-(acetyloxy)-1a,2,3,3a,4,7b-hexahydro-3,3',3',3a-tetramethyl-, (1aR-(1aα,2β,3β,3aβ,5β,7bα))-

Experimental data
Predicted - ACD/Labs
Predicted - EPISuite
Predicted - ChemAxon

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

Density:	1.3±0.1 g/cm³
Boiling Point:	426.3±45.0 °C at 760 mmHg
Vapour Pressure:	0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization:	68.1±3.0 kJ/mol
Flash Point:	225.1±16.7 °C
Index of Refraction:	1.553
Molar Refractivity:	77.7±0.4 cm³
#H bond acceptors:	5
#H bond donors:	0
#Freely Rotating Bonds:	2
#Rule of 5 Violations:	0

ACD/LogP:	0.56
ACD/LogD (pH 5.5):	1.27
ACD/BCF (pH 5.5):	5.41
ACD/KOC (pH 5.5):	116.53
ACD/LogD (pH 7.4):	1.27
ACD/BCF (pH 7.4):	5.41
ACD/KOC (pH 7.4):	116.53
Polar Surface Area:	68 Å²
Polarizability:	30.8±0.5 10^-24cm³
Surface Tension:	45.0±5.0 dyne/cm
Molar Volume:	242.8±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) =  2.90

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  369.01  (Adapted Stein & Brown method)
    Melting Pt (deg C):  143.92  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.91E-006  (Modified Grain method)
    Subcooled liquid VP: 4.65E-005 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):  37.88
       log Kow used: 2.90 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  287.21 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.29E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.097E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.90  (KowWin est)
  Log Kaw used:  -9.278  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.178
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.4638
   Biowin2 (Non-Linear Model)     :   0.0001
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9862  (months      )
   Biowin4 (Primary Survey Model) :   3.1327  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5457
   Biowin6 (MITI Non-Linear Model):   0.0987
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.3347
 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):  0.0062 Pa (4.65E-005 mm Hg)
  Log Koa (Koawin est  ): 12.178
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000484 
       Octanol/air (Koa) model:  0.37 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0172 
       Mackay model           :  0.0373 
       Octanol/air (Koa) model:  0.967 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  92.2994 E-12 cm3/molecule-sec
      Half-Life =     0.116 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.391 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): 0.0272 (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]:
  Total Kb for pH > 8 at 25 deg C :  2.805E-003  L/mol-sec
  Kb Half-Life at pH 8:       7.829  years  
  Kb Half-Life at pH 7:      78.287  years  

  Total Ka (acid-catalyzed) at 25 deg C :  8.892E+009  L/mol-sec [cis-isomer]
  Total Ka (acid-catalyzed) at 25 deg C :  2.084E+009  L/mol-sec [trans-isomer]
  Ka Half-Life at pH 7:       0.001  seconds  [cis-isomer]
  Ka Half-Life at pH 7:       0.003  seconds  [trans-isomer]
 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.530 (BCF = 33.9)
       log Kow used: 2.90 (estimated)

 Volatilization from Water:
    Henry LC:  1.29E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.944E+007  hours   (3.31E+006 days)
    Half-Life from Model Lake : 8.666E+008  hours   (3.611E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               4.92  percent
    Total biodegradation:        0.12  percent
    Total sludge adsorption:     4.81  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       6.81e-005       2.49         1000       
   Water     11.2            1.44e+003    1000       
   Soil      88.5            2.88e+003    1000       
   Sediment  0.223           1.3e+004     0          
     Persistence Time: 2.63e+003 hr

Click to predict properties on the Chemicalize site

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(1aR,2R,3R,3aR,7bS)-3,3',3',3a-Tetramethyl-6-oxo-2,3,3a,4,6,7b-hexahydro-1aH-spiro[naphtho[1,2-b]oxirene-5,2'-oxiran]-2-yl acetate

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