ChemSpider 2D Image | S-Allyl-L-cysteine | C6H11NO2S

S-Allyl-L-cysteine

  • Molecular FormulaC6H11NO2S
  • Average mass161.222 Da
  • Monoisotopic mass161.051056 Da
  • ChemSpider ID7969672

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

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

S-Allyl-L-cysteine [ACD/IUPAC Name]
(+)-S-Allylcysteine
(2R)-3-(Allylthio)-2-aminopropanoic acid
(R)-3-(Allylthio)-2-aminopropanoic acid
(R)-Allylthio-2-aminopropanoic acid
21593-77-1 [RN]
81R3X99M15
HA2466200
L-Cysteine, S-2-propen-1-yl
L-Cysteine, S-2-propen-1-yl- [ACD/Index Name]
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  • Miscellaneous

    • Appearance:

      White powder; Cooked roasted brown aroma Food and Agriculture Organization of the United Nations S-Allyl-L-cysteine

    • Chemical Class:

      An <element>S</element>-hydrocarbyl-<stereo>L</stereo>-cysteine that is <stereo>L</stereo>-cysteine in which the hydrogen attached to the sulphur is replaced by a prop-2-enyl group. It commonly occur s in garlic and has been found to exhibit antineoplastic activity. ChEBI CHEBI:133648, CHEBI:74077
      An <stereo>L</stereo>-<locant>alpha</locant>-amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of <element>S</element>-allylcysteine. Major species at pH 7.3. ChEBI CHEBI:133648, CHEBI:74077
      An L-alpha-amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of S-allylcysteine. Major species at pH 7.3. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:133648, CHEBI:133648
      An S-hydrocarbyl-L-cysteine that is L-cysteine in which the hydrogen attached to the sulphur is replaced by a prop-2-enyl group. It commonly occur; s in garlic and has been found to exhibit antineopl astic activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:74077
      An S-hydrocarbyl-L-cysteine that is L-cysteine in which the hydrogen attached to the sulphur is replaced by a prop-2-enyl group. It commonly occurs in garlic and has been found to exhibit antineoplas tic activity. ChEBI CHEBI:74077

    • Compound Source:

      alliin metabolism PlantCyc CPD-9298
      Linum usitatissimum PlantCyc CPD-9298

    • Bio Activity:

      gamma-L-glutamyl-(S)-allyl-L-cysteine + H2O -> S-allyl-L-cysteine + L-glutamate PlantCyc CPD-9298
      S-allyl-L-cysteine + oxygen + H2O -> alliin + hydrogen peroxide PlantCyc CPD-9298

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

Density: 1.2±0.1 g/cm3
Boiling Point: 300.3±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 59.4±6.0 kJ/mol
Flash Point: 135.4±27.9 °C
Index of Refraction: 1.543
Molar Refractivity: 42.6±0.3 cm3
#H bond acceptors: 3
#H bond donors: 3
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 1.31
ACD/LogD (pH 5.5): -1.56
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.59
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 89 Å2
Polarizability: 16.9±0.5 10-24cm3
Surface Tension: 49.4±3.0 dyne/cm
Molar Volume: 135.3±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) =  -2.06

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  375.62  (Adapted Stein & Brown method)
    Melting Pt (deg C):  225.71  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.28E-007  (Modified Grain method)
    Subcooled liquid VP: 3.23E-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):  3.291e+004
       log Kow used: -2.06 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  16215 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.09E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.470E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.06  (KowWin est)
  Log Kaw used:  -9.068  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.008
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8973
   Biowin2 (Non-Linear Model)     :   0.9222
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2319  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0440  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5137
   Biowin6 (MITI Non-Linear Model):   0.3932
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8657
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.00431 Pa (3.23E-005 mm Hg)
  Log Koa (Koawin est  ): 7.008
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000697 
       Octanol/air (Koa) model:  2.5E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0245 
       Mackay model           :  0.0528 
       Octanol/air (Koa) model:  0.0002 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  82.4097 E-12 cm3/molecule-sec
      Half-Life =     0.130 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.557 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.200000 E-17 cm3/molecule-sec
      Half-Life =     0.955 Days (at 7E11 mol/cm3)
      Half-Life =     22.920 Hrs
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.0387 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  17.26
      Log Koc:  1.237 

 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 = 0.500 (BCF = 3.162)
       log Kow used: -2.06 (estimated)

 Volatilization from Water:
    Henry LC:  2.09E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.557E+007  hours   (1.482E+006 days)
    Half-Life from Model Lake :  3.88E+008  hours   (1.617E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       0.000512        2.74         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0714          3.24e+003    0          
     Persistence Time: 578 hr

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