You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 19:11:23 UTC
Update Date2019-07-23 06:15:52 UTC
HMDB IDHMDB0034365
Secondary Accession Numbers
  • HMDB0062764
  • HMDB34365
  • HMDB62764
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
Data?1563862552
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
Chemical FormulaC7H14N2O3
Average Molecular Weight174.1977
Monoisotopic Molecular Weight174.100442324
IUPAC Name(2S)-2-amino-4-(ethylcarbamoyl)butanoic acid
Traditional Nametheanine
CAS Registry Number3081-61-6
SMILES
CCNC(=O)CC[C@H](N)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
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamine 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point217 - 218 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility48.3 g/LALOGPS
logP-2.5ALOGPS
logP-3.4ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.35ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity42.76 m³·mol⁻¹ChemAxon
Polarizability17.89 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-05ai-1910000000-036caaf79935b62dafb8Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0ik9-2920000000-b4175a19d175fc2dfaabSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9200000000-ad824a92c4a91b92d3beSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0kmr-9420000000-fd2f30cc6e3beb84fc83Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-5d75f1c18d21692a3a7aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-1900000000-30f94d8454c885920222Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9300000000-533425b383afd6ea8b10Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0089-9000000000-cd51416fce1d90ca5a32Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001l-9000000000-d11379cff212e4305279Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a59-4900000000-233828d22b124785b538Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9100000000-c68d3e3853f38b6441ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-1d437318f6185e9abed1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-053r-9000000000-f98a061445440bd8d92fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-7900000000-700a74673280513b750aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-c05118c6382a21ee49c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-5900d952e786b1c37b5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-ba1082ef889273ac4decSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i3-4900000000-74c4e555cb1b6dd5de58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-854bf36c0c647d7b14a4Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.0499 +/- 0.108 uMAdult (>18 years old)BothNormal
    • Sugimoto et al. (...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.110 +/- 0.132 uMAdult (>18 years old)BothOral cavity disorders
    • Sugimoto et al. (...
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12444
Phenol Explorer Compound IDNot Available
FooDB IDFDB012738
KNApSAcK IDC00030691
Chemspider ID388498
KEGG Compound IDC01047
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkL-theanine
METLIN IDNot Available
PubChem Compound439378
PDB IDNot Available
ChEBI ID17394
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .