ChemSpider 2D Image | (S)-(-)-atropine | C17H23NO3

(S)-(-)-atropine

  • Molecular FormulaC17H23NO3
  • Average mass289.369 Da
  • Monoisotopic mass289.167786 Da
  • ChemSpider ID10246417
  • defined stereocentres - 4 of 4 defined stereocentres


More details:






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

(S)-(-)-atropine
(-)-atropine
(-)-Hyoscyamine
(2S)-3-Hydroxy-2-phénylpropanoate de (3-endo)-8-méthyl-8-azabicyclo[3.2.1]oct-3-yle [French] [ACD/IUPAC Name]
(3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl (2S)-3-hydroxy-2-phenylpropanoate [ACD/IUPAC Name]
(3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl-(2S)-3-hydroxy-2-phenylpropanoat
(3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl-(2S)tropaat [German] [ACD/IUPAC Name]
(L)-Phenylalanine [RN]
(S)-(-)-hyoscyamine
(S)-atropine
More...

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

HSDB 3552 [DBID]
AIDS012108 [DBID]
AIDS-012108 [DBID]
C02046 [DBID]
CHEBI:17486 [DBID]
D00147 [DBID]
NSC61808 (HCL) [DBID]
Prestwick_273 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      A03BA03 Wikidata Q413762
    • Chemical Class:

      An atropine with a 2<stereo>S</stereo>-configuration. ChEBI CHEBI:17486
    • Bio Activity:

      GPCR/G protein MedChem Express HY-N0471
      GPCR/G protein; Neuronal Signaling; MedChem Express HY-N0471
      L-Hyoscyamine is a chemical compound, a tropane alkaloid it is the levo-isomer to atropine. MedChem Express
      L-Hyoscyamine is a chemical compound, a tropane alkaloid it is the levo-isomer to atropine.; Target: mAChR; Hyoscyamine is a chemical compound, a tropane alkaloid it is the levo-isomer to atropine. MedChem Express HY-N0471
      L-Hyoscyamine is a chemical compound, a tropane alkaloid it is the levo-isomer to atropine.;Target: mAChRHyoscyamine is a chemical compound, a tropane alkaloid it is the levo-isomer to atropine. It is a secondary metabolite of some plants, particularly henbane (Hyoscamus niger.)Hyoscyamine is used to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinson's disease, as well as for control of respiratory secretions in end of life care [1]. MedChem Express HY-N0471
      mAChR MedChem Express HY-N0471

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

Density: 1.2±0.1 g/cm3
Boiling Point: 429.8±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 72.2±3.0 kJ/mol
Flash Point: 213.7±28.7 °C
Index of Refraction: 1.581
Molar Refractivity: 80.8±0.4 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 1.53
ACD/LogD (pH 5.5): -1.23
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -0.61
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 50 Å2
Polarizability: 32.0±0.5 10-24cm3
Surface Tension: 50.5±5.0 dyne/cm
Molar Volume: 242.4±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) =  1.91
    Log Kow (Exper. database match) =  1.83
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  393.05  (Adapted Stein & Brown method)
    Melting Pt (deg C):  141.76  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.49E-008  (Modified Grain method)
    MP  (exp database):  108.5 deg C
    Subcooled liquid VP: 2.96E-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):  3944
       log Kow used: 1.83 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  2200 mg/L (25 deg C)
        Exper. Ref:  DEHN,WM (1917)
     Water Sol (Exper. database match) =  3560 mg/L (20 deg C)
        Exper. Ref:  MERCK INDEX (1996); pH 9.5

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5228.1 mg/L
    Wat Sol (Exper. database match) =  2200.00
       Exper. Ref:  DEHN,WM (1917)
    Wat Sol (Exper. database match) =  3560.00
       Exper. Ref:  MERCK INDEX (1996); pH 9.5

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.73E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.335E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.83  (exp database)
  Log Kaw used:  -10.952  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.782
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9202
   Biowin2 (Non-Linear Model)     :   0.9859
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5522  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4370  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4687
   Biowin6 (MITI Non-Linear Model):   0.2062
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6898
 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):  3.95E-005 Pa (2.96E-007 mm Hg)
  Log Koa (Koawin est  ): 12.782
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.076 
       Octanol/air (Koa) model:  1.49 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.733 
       Mackay model           :  0.859 
       Octanol/air (Koa) model:  0.992 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  61.0607 E-12 cm3/molecule-sec
      Half-Life =     0.175 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.102 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.796 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  689.6
      Log Koc:  2.839 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.286E-003  L/mol-sec
  Kb Half-Life at pH 8:       9.609  years  
  Kb Half-Life at pH 7:      96.093  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.059 (BCF = 1.146)
       log Kow used: 1.83 (expkow database)

 Volatilization from Water:
    Henry LC:  2.73E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.648E+009  hours   (1.52E+008 days)
    Half-Life from Model Lake :  3.98E+010  hours   (1.658E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               2.12  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     2.02  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       6.7e-006        4.2          1000       
   Water     26.3            900          1000       
   Soil      73.6            1.8e+003     1000       
   Sediment  0.0848          8.1e+003     0          
     Persistence Time: 1.34e+003 hr




                    

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