ChemSpider 2D Image | L-Theanine | C7H14N2O3

L-Theanine

  • Molecular FormulaC7H14N2O3
  • Average mass174.198 Da
  • Monoisotopic mass174.100449 Da
  • ChemSpider ID388498

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

L-Theanine
(2S)-2-amino-4-(ethylcarbamoyl)butanoic acid
(5Z)-5-(Ethylimino)-5-hydroxy-L-norvalin [German] [ACD/IUPAC Name]
(5Z)-5-(Ethylimino)-5-hydroxy-L-norvaline [ACD/IUPAC Name]
(5Z)-5-(Éthylimino)-5-hydroxy-L-norvaline [French] [ACD/IUPAC Name]
221-379-0 [EINECS]
3081-61-6 [RN]
8021PR16QO
L-Glutamic acid γ-(ethylamide)
L-Glutamine, N-ethyl- [ACD/Index Name]
More...

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

C01047 [DBID]
CCRIS 4693 [DBID]
CHEBI:17394 [DBID]
KBio3_002133 [DBID]
KBioGR_002514 [DBID]
SDCCGMLS-0066811.P001 [DBID]
SPBio_001646 [DBID]
Spectrum2_001693 [DBID]
Spectrum3_001137 [DBID]
Spectrum4_001984 [DBID]
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A <element>N</element><smallsup>5</smallsup>-alkylglutamine where the alkyl group is ethyl. It has been isolated from green tea. ChEBI CHEBI:17394, CHEBI:58128
      A N(5)-alkylglutamine where the alkyl group is ethyl. It has been isolated from green tea. ChEBI CHEBI:17394
      A N5-alkylglutamine where the alkyl group is ethyl. It has been isolated from green tea. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17394
      An amino acid zwitterion of <element>N</element><smallsup>5</smallsup>-ethyl-<stereo>L</stereo>-glutamine arising from transfer of a proton from the carboxy to the amino group; major species at pH 7.3 . ChEBI CHEBI:17394, CHEBI:58128
      An amino acid zwitterion of N(5)-ethyl-L-glutamine arising from transfer of a proton from the carboxy to the amino group; major species at pH 7.3. ChEBI CHEBI:58128
      An amino acid zwitterion of N5-ethyl-L-glutamine arising from transfer of a proton from the carboxy to the amino group; major species at pH 7.3; . ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:58128

    • Bio Activity:

      7-TM Receptors Tocris Bioscience 3847
      Amino acid analog of glutamine and component of green tea. Shown to bind to AMPA, Kainate, NMDA and group I mGlu receptors. Displays neuroprotective effects in vivo. Promotes self-renewal of human emb ryonic stem cells (hESC). Tocris Bioscience 3847
      Amino acid analog of glutamine and component of green tea. Shown to bind to AMPA, Kainate, NMDA and group I mGlu receptors. Displays neuroprotective effects in vivo. Promotes self-renewal of human embryonic stem cells (hESC). Tocris Bioscience 3847
      Amino acid analog of Glutamine. Also binds to NMDA glycine, kainate and AMPA receptors (IC<sub>50</sub> vales are 347, 41.5 and 24.6 &micro;M respectively). Blood brain barrier permeable and down regulates COX-2 expression. Displays antioxidant and neuroprotective properties. Also promotes hESC self-renewal. Hello Bio HB0612
      Amino acid analog of Glutamine. Promotes hESC self-renewal. Hello Bio HB0612
      Cell process/Stem cells/Proliferation Hello Bio HB0612
      Glutamate (Ionotropic) Receptors Tocris Bioscience 3847
      Glutamate (Metabotropic) Receptors Tocris Bioscience 3847
      Glutamate receptor ligand Tocris Bioscience 3847
      Ion Channels Tocris Bioscience 3847
      Ion channels/Ligand-gated ion channel/Ionotropic glutamate receptors/NMDA Hello Bio HB0612
      Ligand-gated Ion Channels Tocris Bioscience 3847
      Miscellaneous Glutamate Tocris Bioscience 3847
      Receptors & Transporters/G protein coupled receptors/Metabotropic glutamate/Miscellaneous Hello Bio HB0612
      Type/Biochemicals & small molecules Hello Bio HB0612

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

Density: 1.2±0.1 g/cm3
Boiling Point: 430.2±40.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 75.2±6.0 kJ/mol
Flash Point: 214.0±27.3 °C
Index of Refraction: 1.492
Molar Refractivity: 43.2±0.3 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: -1.02
ACD/LogD (pH 5.5): -3.34
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.34
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 92 Å2
Polarizability: 17.1±0.5 10-24cm3
Surface Tension: 48.2±3.0 dyne/cm
Molar Volume: 148.7±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) =  -3.54

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  407.95  (Adapted Stein & Brown method)
    Melting Pt (deg C):  292.20  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.69E-009  (Modified Grain method)
    Subcooled liquid VP: 5.32E-006 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):  2.567e+004
       log Kow used: -3.54 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 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 :   8.77E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.081E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -3.54  (KowWin est)
  Log Kaw used:  -13.445  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.905
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1013
   Biowin2 (Non-Linear Model)     :   0.9932
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1490  (weeks       )
   Biowin4 (Primary Survey Model) :   4.2307  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6330
   Biowin6 (MITI Non-Linear Model):   0.6084
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4648
 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):  0.000709 Pa (5.32E-006 mm Hg)
  Log Koa (Koawin est  ): 9.905
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00423 
       Octanol/air (Koa) model:  0.00197 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.133 
       Mackay model           :  0.253 
       Octanol/air (Koa) model:  0.136 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  53.0024 E-12 cm3/molecule-sec
      Half-Life =     0.202 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.422 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.193 (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: -3.54 (estimated)

 Volatilization from Water:
    Henry LC:  8.77E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.811E+011  hours   (3.671E+010 days)
    Half-Life from Model Lake : 9.612E+012  hours   (4.005E+011 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       2.81e-008       4.84         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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