ChemSpider 2D Image | (+)-Amabiline | C15H25NO4

(+)-Amabiline

  • Molecular FormulaC15H25NO4
  • Average mass283.363 Da
  • Monoisotopic mass283.178345 Da
  • ChemSpider ID391061

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

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

(+)-Amabiline
(2S,3S)-2,3-Dihydroxy-2-isopropylbutanoate de (7aS)-2,3,5,7a-tétrahydro-1H-pyrrolizin-7-ylméthyle [French] [ACD/IUPAC Name]
(7aS)-2,3,5,7a-Tetrahydro-1H-pyrrolizin-7-ylmethyl (2S,3S)-2,3-dihydroxy-2-isopropylbutanoate [ACD/IUPAC Name]
(7aS)-2,3,5,7a-Tetrahydro-1H-pyrrolizin-7-ylmethyl-(2S,3S)-2,3-dihydroxy-2-isopropylbutanoat [German] [ACD/IUPAC Name]
[(7aS)-2,3,5,7a-Tetrahydro-1H-pyrrolizin-7-yl]methyl (2S,3S)-2,3-dihydroxy-2-(1-methylethyl)butanoate
17958-43-9 [RN]
Amabiline
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, [(7aS)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl ester, (2S,3S)- [ACD/Index Name]
(2S,3S)-2,3-DIHYDROXY-2-ISOPROPYLBUTANOIC ACID [(5S)-1-AZABICYCLO[3.3.0]OCT-3-EN-4-YL]METHYL ESTER
(7aS)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-ylmethyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C10263 [DBID]
CHEBI:2617 [DBID]
  • Miscellaneous

    • Chemical Class:

      A carboxylic ester obtained by formal condensation of the carboxy group of (2<stereo>S</stereo>,3<stereo>S</stereo>)-2,3-dihydroxy-2-isopropylbutanoic acid with the hydroxy group of (7a<stereo>S</ster eo>)-2,3,5,7a-tetrahydropyrrolizin-7-ylmethanol. ChEBI CHEBI:2617
      A carboxylic ester obtained by formal condensation of the carboxy group of (2S,3S)-2,3-dihydroxy-2-isopropylbutanoic acid with the hydroxy group of (7aS)-2,3,5,7a-tetrahydropyrrolizin-7-ylmethanol. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2617, CHEBI:2617

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

Density: 1.2±0.1 g/cm3
Boiling Point: 416.8±24.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 77.4±6.0 kJ/mol
Flash Point: 205.9±22.9 °C
Index of Refraction: 1.549
Molar Refractivity: 75.8±0.4 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 0.90
ACD/LogD (pH 5.5): -1.91
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.02
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 70 Å2
Polarizability: 30.1±0.5 10-24cm3
Surface Tension: 49.2±5.0 dyne/cm
Molar Volume: 238.5±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) =  2.45

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  374.50  (Adapted Stein & Brown method)
    Melting Pt (deg C):  138.90  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.28E-008  (Modified Grain method)
    Subcooled liquid VP: 4.62E-007 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):  1258
       log Kow used: 2.45 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5.3435e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.70E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.722E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.45  (KowWin est)
  Log Kaw used:  -7.158  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.608
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5564
   Biowin2 (Non-Linear Model)     :   0.5587
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4062  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3559  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4036
   Biowin6 (MITI Non-Linear Model):   0.1807
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.3269
 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):  6.16E-005 Pa (4.62E-007 mm Hg)
  Log Koa (Koawin est  ): 9.608
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0487 
       Octanol/air (Koa) model:  0.000995 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.638 
       Mackay model           :  0.796 
       Octanol/air (Koa) model:  0.0738 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 151.6456 E-12 cm3/molecule-sec
      Half-Life =     0.071 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.846 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    43.000000 E-17 cm3/molecule-sec
      Half-Life =     0.027 Days (at 7E11 mol/cm3)
      Half-Life =     38.378 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.717 (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 :  3.732E-006  L/mol-sec
  Kb Half-Life at pH 8:    5885.616  years  
  Kb Half-Life at pH 7: 5.886E+004  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.188 (BCF = 15.41)
       log Kow used: 2.45 (estimated)

 Volatilization from Water:
    Henry LC:  1.7E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.798E+005  hours   (2.416E+004 days)
    Half-Life from Model Lake : 6.325E+006  hours   (2.635E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               2.96  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.86  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       0.0151          0.464        1000       
   Water     21              900          1000       
   Soil      78.8            1.8e+003     1000       
   Sediment  0.158           8.1e+003     0          
     Persistence Time: 1.11e+003 hr

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