Showing metabocard for L-Theanine (MMDBc0000670)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:52:22 UTC
Update Date2024-10-10 00:46:46 UTC
Metabolite IDMMDBc0000670
Metabolite Identification
Common NameL-Theanine
DescriptionL-Theanine, also known as L-gamma-glutamylethylamide or N-gamma-ethyl-L-glutamine, is a member of the class of compounds known as glutamine and derivatives. These compounds contain glutamine or a derivative thereof resulting from a reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Theanine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). L-Theanine can be found in saliva. The regulatory status of theanine varies by country. In Japan, L-theanine has been approved for use in all foods, including herb teas, soft drinks, and desserts. Restrictions apply to infant foods. In the United States, the Food and Drug Administration (FDA) considers it to be generally recognized as safe (GRAS) and allows its sale as a dietary supplement. The German Federal Institute for Risk Assessment, an agency of their Federal Ministry of Food and Agriculture, objects to the addition of L-theanine to beverages. The European Food Safety Authority EFSA advised negatively on health claims related to L-theanine and cognitive function, alleviation of psychological stress, maintenance of normal sleep, and reduction of menstrual discomfort. Therefore, health claims for L-theanine are prohibited in the European Union (Wikipedia ). L-Theanine is found in mushrooms and is a constituent of tea (Thea sinensis) and of the fungus Imleria badia. L-Theanine has been shown to exhibit neuroprotectant and neuroprotective functions (PMID: 20416364 , 20416364 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f920c422ac0>


  Mrv1652307171819472D          

 13 12  0  0  1  0            999 V2000
   -2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  5  8  1  1  0  0  0
  9  2  1  4  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
  5 13  1  1  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f920c422ac0>

HMDB0034365
     RDKit          3D
L-Theanine
 26 25  0  0  0  0  0  0  0  0999 V2000
   -4.0444    0.6780   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5604   -0.7519   -0.6231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1864   -0.7967   -1.0560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1315   -0.2422   -0.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3999    0.3112    0.8085 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807   -0.2768   -0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1879    0.3828    0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6258    0.3304   -0.1796 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0478   -1.0320   -0.3426 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4938    1.0406    0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2860    2.2475    1.0663 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5419    0.3530    1.3822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9220    0.9476    0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1248    0.6879   -0.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4723    1.3773   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5983   -1.2699    0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330   -1.2839   -1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9635   -1.2528   -1.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655    0.1862   -1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6023   -1.3442   -0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1015   -0.1460    1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8788    1.4580    0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6767    0.8200   -1.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7071   -1.6499    0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8106   -1.4268   -1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0299    0.6526    2.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  6
  9 24  1  0
  9 25  1  0
 12 26  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f920c422ac0>


  Mrv1652307171819472D          

 13 12  0  0  1  0            999 V2000
   -2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  5  8  1  1  0  0  0
  9  2  1  4  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
  5 13  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000670

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(CCC(O)=NCC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H14N2O3/c1-2-9-6(10)4-3-5(8)7(11)12/h5H,2-4,8H2,1H3,(H,9,10)(H,11,12)/t5-/m0/s1

> <INCHI_KEY>
DATAGRPVKZEWHA-YFKPBYRVSA-N

> <FORMULA>
C7H14N2O3

> <MOLECULAR_WEIGHT>
174.1977

> <EXACT_MASS>
174.100442324

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.893479520544766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-(ethylcarbamoyl)butanoic acid

> <ALOGPS_LOGP>
-2.52

> <JCHEM_LOGP>
-3.420373292461693

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.887736304027854

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.352835582578874

> <JCHEM_PKA_STRONGEST_BASIC>
9.312088036289436

> <JCHEM_POLAR_SURFACE_AREA>
92.41999999999999

> <JCHEM_REFRACTIVITY>
42.7552

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
theanine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f920c422ac0>

HMDB0034365
     RDKit          3D
L-Theanine
 26 25  0  0  0  0  0  0  0  0999 V2000
   -4.0444    0.6780   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5604   -0.7519   -0.6231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1864   -0.7967   -1.0560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1315   -0.2422   -0.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3999    0.3112    0.8085 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807   -0.2768   -0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1879    0.3828    0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6258    0.3304   -0.1796 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0478   -1.0320   -0.3426 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4938    1.0406    0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2860    2.2475    1.0663 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5419    0.3530    1.3822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9220    0.9476    0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1248    0.6879   -0.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4723    1.3773   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5983   -1.2699    0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330   -1.2839   -1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9635   -1.2528   -1.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655    0.1862   -1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6023   -1.3442   -0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1015   -0.1460    1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8788    1.4580    0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6767    0.8200   -1.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7071   -1.6499    0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8106   -1.4268   -1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0299    0.6526    2.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  6
  9 24  1  0
  9 25  1  0
 12 26  1  0
M  END
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PDB for #<Metabolite:0x00007f920c422ac0>

HEADER    PROTEIN                                 17-JUL-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-18         0                                  
HETATM    1  C   UNK     0      -4.358   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.025   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      -1.691   2.104   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -0.357  -0.206   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0       3.644   0.564   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    9                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7    8   13                                             
CONECT    6    4    9   10                                                  
CONECT    7    5   11   12                                                  
CONECT    8    5                                                            
CONECT    9    2    6                                                       
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    5                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for #<Metabolite:0x00007f920c422ac0>

COMPND    HMDB0034365
HETATM    1  C1  UNL     1      -4.044   0.678  -0.443  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.560  -0.752  -0.623  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.186  -0.797  -1.056  1.00  0.00           N  
HETATM    4  C3  UNL     1      -1.132  -0.242  -0.291  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.400   0.311   0.809  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.281  -0.277  -0.715  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.188   0.383   0.284  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.626   0.330  -0.180  1.00  0.00           C  
HETATM    9  N2  UNL     1       3.048  -1.032  -0.343  1.00  0.00           N  
HETATM   10  C7  UNL     1       3.494   1.041   0.787  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.286   2.248   1.066  1.00  0.00           O  
HETATM   12  O3  UNL     1       4.542   0.353   1.382  1.00  0.00           O  
HETATM   13  H1  UNL     1      -3.922   0.948   0.622  1.00  0.00           H  
HETATM   14  H2  UNL     1      -5.125   0.688  -0.664  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.472   1.377  -1.085  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.598  -1.270   0.377  1.00  0.00           H  
HETATM   17  H5  UNL     1      -4.233  -1.284  -1.299  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.963  -1.253  -1.963  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.365   0.186  -1.721  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.602  -1.344  -0.787  1.00  0.00           H  
HETATM   21  H9  UNL     1       1.102  -0.146   1.246  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.879   1.458   0.383  1.00  0.00           H  
HETATM   23  H11 UNL     1       2.677   0.820  -1.181  1.00  0.00           H  
HETATM   24  H12 UNL     1       2.707  -1.650   0.445  1.00  0.00           H  
HETATM   25  H13 UNL     1       2.811  -1.427  -1.283  1.00  0.00           H  
HETATM   26  H14 UNL     1       5.030   0.653   2.207  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4   18
CONECT    4    5    5    6
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9   10   23
CONECT    9   24   25
CONECT   10   11   11   12
CONECT   12   26
END
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SMILES for #<Metabolite:0x00007f920c422ac0>

[H][C@](N)(CCC(O)=NCC)C(O)=O
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INCHI for #<Metabolite:0x00007f920c422ac0>

InChI=1S/C7H14N2O3/c1-2-9-6(10)4-3-5(8)7(11)12/h5H,2-4,8H2,1H3,(H,9,10)(H,11,12)/t5-/m0/s1
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Synonyms
ValueSource
N5-Ethyl-L-glutamineChEBI
gamma-GlutamylethylamideHMDB
Theanine, (D)-isomerHMDB
L-Glutamic acid-gamma-ethylamideHMDB
Theanine, (DL)-isomerHMDB
delta-GlutamylethylamideHMDB
Theanine, (L)-isomerHMDB
(+)-TheanineHMDB
L-gamma-GlutamylethylamideHMDB
L-Γ-glutamylethylamideHMDB
N-gamma-Ethyl-L-glutamineHMDB
N-Γ-ethyl-L-glutamineHMDB
Nγ-ethyl-L-glutamineHMDB
SuntheanineHMDB
TheaninHMDB
N(5)-Ethyl-L-glutamineHMDB
TheanineHMDB
L-TheanineChEBI
Molecular FormulaC7H14N2O3
Average Mass174.1977
Monoisotopic Mass174.100442324
IUPAC Name(2S)-2-amino-4-(ethylcarbamoyl)butanoic acid
Traditional Nametheanine
CAS Registry NumberNot Available
SMILES
[H][C@](N)(CCC(O)=NCC)C(O)=O
InChI Identifier
InChI=1S/C7H14N2O3/c1-2-9-6(10)4-3-5(8)7(11)12/h5H,2-4,8H2,1H3,(H,9,10)(H,11,12)/t5-/m0/s1
InChI KeyDATAGRPVKZEWHA-YFKPBYRVSA-N