ChemSpider 2D Image | L-(+)-ERGOTHIONEINE | C9H15N3O2S

L-(+)-ERGOTHIONEINE

  • Molecular FormulaC9H15N3O2S
  • Average mass229.299 Da
  • Monoisotopic mass229.088501 Da
  • ChemSpider ID4508619
  • defined stereocentres - 1 of 1 defined stereocentres


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L-(+)-ERGOTHIONEINE
(2S)-3-(2-Sulfanyl-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate
(2S)-3-(2-Thioxo-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylammonio)propanoat [German] [ACD/IUPAC Name]
(2S)-3-(2-Thioxo-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylammonio)propanoate [ACD/IUPAC Name]
(2S)-3-(2-Thioxo-2,3-dihydro-1H-imidazol-4-yl)-2-(triméthylammonio)propanoate [French] [ACD/IUPAC Name]
(S)-a-Carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium Hydroxide Inner Salt
[1-Carboxy-2-[2-mercaptoimidazol-4(or 5)-yl]ethyl]trimethylammonium Hydroxide Inner Salt
1H-Imidazole-4-ethanaminium, α-carboxy-2-mercapto-N,N,N-trimethyl-, inner salt, (αS)- [ACD/Index Name]
1H-imidazole-5-ethanaminium, α-carboxy-2-mercapto-N,N,N-trimethyl-, inner salt, (αS)-
207-843-5 [EINECS]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

E7521_SIGMA [DBID]
NSC 7175 [DBID]
NSC7175 [DBID]
ZINC01530224 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A <stereo>L</stereo>-histidine derivative that is <element>N</element><smallsup><locant>alpha</locant></smallsup>,<element>N</element><smallsup><locant>alpha</locant></smallsup>,<element>N</element><s mallsup><locant>alpha</locant></smallsup>-trimethyl-<stereo>L</stereo>-histidine in which the hydrogen at position 2 on the imdazole ring is replaced by a mercapto group. A naturally occurring metabol ite of histidine synthesized by bacteria and fungi with antioxidant properties. It is found ubiquitously in plants and animals and is present in many human foodstuffs. ChEBI CHEBI:4828, CHEBI:82707
      A <stereo>L</stereo>-histidine derivative that is <element>N</element><smallsup><locant>alpha</locant></smallsup>,<element>N</element><smallsup><locant>alpha</locant></smallsup>,<element>N</element><s mallsup><locant>alpha</locant></smallsup>-trimethyl-<stereo>L</stereo>-histidine in which the hydrogen at position 2 on the imdazole ring is replaced by a thioxo group. ChEBI CHEBI:4828, CHEBI:82707

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

Density:
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction:
Molar Refractivity:
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: -3.43
ACD/LogD (pH 5.5): -3.09
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.09
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 108 Å2
Polarizability:
Surface Tension:
Molar Volume:

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -4.25

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  573.21  (Adapted Stein & Brown method)
    Melting Pt (deg C):  246.79  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.44E-012  (Modified Grain method)
    Subcooled liquid VP: 3.67E-010 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):  1e+006
       log Kow used: -4.25 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  11661 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.62E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.364E-019 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -4.25  (KowWin est)
  Log Kaw used:  -18.179  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.929
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9207
   Biowin2 (Non-Linear Model)     :   0.9558
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0006  (weeks       )
   Biowin4 (Primary Survey Model) :   4.1065  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3317
   Biowin6 (MITI Non-Linear Model):   0.1929
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4348
 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):  4.89E-008 Pa (3.67E-010 mm Hg)
  Log Koa (Koawin est  ): 13.929
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  61.3 
       Octanol/air (Koa) model:  20.8 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 179.3910 E-12 cm3/molecule-sec
      Half-Life =     0.060 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.715 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): 1 (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]:
    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: -4.25 (estimated)

 Volatilization from Water:
    Henry LC:  1.62E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.485E+016  hours   (2.285E+015 days)
    Half-Life from Model Lake : 5.983E+017  hours   (2.493E+016 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       1.53e-009       1.35         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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