MiMeDB: Showing metabocard for L-Theanine (MMDBc0000670)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:52:22 UTC

Update Date

2024-10-10 00:46:46 UTC

Metabolite ID

MMDBc0000670

Metabolite Identification

Common Name

L-Theanine

Description

L-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

Synonyms

Value	Source
N5-Ethyl-L-glutamine	ChEBI
gamma-Glutamylethylamide	HMDB
Theanine, (D)-isomer	HMDB
L-Glutamic acid-gamma-ethylamide	HMDB
Theanine, (DL)-isomer	HMDB
delta-Glutamylethylamide	HMDB
Theanine, (L)-isomer	HMDB
(+)-Theanine	HMDB
L-gamma-Glutamylethylamide	HMDB
L-Γ-glutamylethylamide	HMDB
N-gamma-Ethyl-L-glutamine	HMDB
N-Γ-ethyl-L-glutamine	HMDB
Nγ-ethyl-L-glutamine	HMDB
Suntheanine	HMDB
Theanin	HMDB
N(5)-Ethyl-L-glutamine	HMDB
Theanine	HMDB
L-Theanine	ChEBI

Molecular Formula

C₇H₁₄N₂O₃

Average Mass

174.1977

Monoisotopic Mass

174.100442324

IUPAC Name

(2S)-2-amino-4-(ethylcarbamoyl)butanoic acid

Traditional Name

theanine

CAS Registry Number

Not 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 Key

DATAGRPVKZEWHA-YFKPBYRVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamine and derivatives

Alternative Parents

Substituents

Glutamine or derivatives
Alpha-amino acid
L-alpha-amino acid
Fatty amide
N-acyl-amine
Fatty acid
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Organic oxide
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N(5)-alkyl-L-glutamine (CHEBI:17394 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.25 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.4	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.35	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	42.76 m³·mol⁻¹	ChemAxon
Polarizability	17.89 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-05ai-1910000000-036caaf79935b62dafb8	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0ik9-2920000000-b4175a19d175fc2dfaab	2014-06-16	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-9200000000-ad824a92c4a91b92d3be	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0kmr-9420000000-fd2f30cc6e3beb84fc83	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0900000000-5d75f1c18d21692a3a7a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-1900000000-30f94d8454c885920222	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9300000000-533425b383afd6ea8b10	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0089-9000000000-cd51416fce1d90ca5a32	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001l-9000000000-d11379cff212e4305279	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a59-4900000000-233828d22b124785b538	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9100000000-c68d3e3853f38b6441eb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-1d437318f6185e9abed1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-053r-9000000000-f98a061445440bd8d92f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0pi9-4900000000-bc5d761afc2906c70f9a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-9400000000-a38f88002cc84f835dbf	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002f-7900000000-700a74673280513b750a	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9300000000-c05118c6382a21ee49c6	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-5900d952e786b1c37b5c	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1900000000-ba1082ef889273ac4dec	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05i3-4900000000-74c4e555cb1b6dd5de58	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-854bf36c0c647d7b14a4	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-0900000000-8ab94ce283e2c855565c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-4900000000-f58dee8213166ad39be4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-ead54ac3cc631ccf43b3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-3900000000-6f8b15731e34783f4301	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9300000000-1c6627be4cfa6191919a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9100000000-20b79ebdc4f84490ec0f	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces
Saliva

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Proteobacteria	1

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Saliva	Detected and Quantified	0.0499	0.108			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0034365

DrugBank ID

DB12444

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

L-theanine

METLIN ID

Not Available

PubChem Compound

439378

PDB ID

Not Available

ChEBI ID

17394

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Di X, Yan J, Zhao Y, Zhang J, Shi Z, Chang Y, Zhao B: L-theanine protects the APP (Swedish mutation) transgenic SH-SY5Y cell against glutamate-induced excitotoxicity via inhibition of the NMDA receptor pathway. Neuroscience. 2010 Jul 14;168(3):778-86. doi: 10.1016/j.neuroscience.2010.04.019. Epub 2010 Apr 21. [PubMed:20416364 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for L-Theanine (MMDBc0000670)

MOL for #<Metabolite:0x00007fdb44debaf8>

3D MOL for #<Metabolite:0x00007fdb44debaf8>

3D SDF for #<Metabolite:0x00007fdb44debaf8>

3D-SDF for #<Metabolite:0x00007fdb44debaf8>

PDB for #<Metabolite:0x00007fdb44debaf8>

3D PDB for #<Metabolite:0x00007fdb44debaf8>

SMILES for #<Metabolite:0x00007fdb44debaf8>

INCHI for #<Metabolite:0x00007fdb44debaf8>

Structure for #<Metabolite:0x00007fdb44debaf8>

3D Structure for #<Metabolite:0x00007fdb44debaf8>