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

• ChemBase ID: 106191
• Molecular Formular: C7H14N2O3
• Molecular Mass: 174.19766
• Monoisotopic Mass: 174.10044232
• SMILES: CCNC(=O)CC[C@H](N)C(=O)O
• Canonical SMILES: CCNC(=O)CC[C@@H](C(=O)O)N
• InChI: 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
• InChIKey: DATAGRPVKZEWHA-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-(ethylcarbamoyl)butanoic acid
• IUPAC Traditional name: theanine
• Synonyms: N-gamma-Ethyl-L-glutamine; L-gamma-Glutamylethylamide; Theanin; L-THEANINE; N^5-Ethyl-L-glutamine; Theanine; Nγ-Ethyl-L-glutamine; L-Glutamic acid γ-(ethylamide); L-Theanine; N-Ethyl-L-glutamine; Suntheanine; Theanine; NSC 21308

Database IDs

• CAS Number: 3081-61-6
• EC Number: 221-379-0; 3081-61-6
• MDL Number: MFCD00059653
• PubChem SID: 162093135; 24900389
• PubChem CID: 439378; 228398
• CHEBI ID: 17394
• Chemspider ID: 198778
• MeSH Name: theanine
• Unique Ingredient Identifier: 8021PR16QO
• Wikipedia Title: Theanine

CALCULATED PROPERTIES

• Acid pKa: 2.3531113
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.4204123
• LogD (pH = 7.4): -3.4250932
• Log P: -3.4203734
• Molar Refractivity: 42.7552 cm^3
• Polarizability: 16.951561 Å^3
• Polar Surface Area: 92.42 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: >190°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 43
• Safety Statements: 28-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Empirical Formula (Hill Notation): C7H14N2O3

DETAILS

Sigma Aldrich - T6576

Biochem/physiol Actions
Theanine is able to bind to AMPA, kainite, and NMDA glycine receptors in rat cortical neurons but with less affinity than glutamic acid.1 It has been studied as a glutamate transport inhibitor, preventing glutamate uptake by M5076 ovarian sarcoma-bearing mouse cells and increasing the effect of doxorubicin on tumor growth in M5076 mice.2
Other Notes
Theanine is an amino acid analog of glutamine, found in green tea.

Toronto Research Chemicals - T340500

A non-protein amino acid mainly found naturally in the green tea plant. It may have activity in modulating the metabolism of cancer chemotherapeutics agents.

REFERENCES

• Yokohoshi, H., et al.: Neurochem Res., 23, 667 (1998)
• Sugiyama, T., et al.: Clin Cancer Res., 5, 413 (1999)