Natural Product (NP) Details

General Information of the NP (ID: NP1411)
Name
Theanine
Synonyms
L-Theanine; Theanine; 3081-61-6; Theanin; N-Ethyl-L-glutamine; Suntheanine; (S)-2-Amino-5-(ethylamino)-5-oxopentanoic acid; N5-Ethyl-L-glutamine; L-gamma-Glutamylethylamide; N(5)-ethyl-L-glutamine; N-gamma-Ethyl-L-glutamine; UNII-8021PR16QO; (2S)-2-amino-5-(ethylamino)-5-oxopentanoic acid; CHEBI:17394; L-Glutamic acid ?-(ethylamide); 8021PR16QO; L-Theanine, 98%; N(5)-ethyl-L-glutamine zwitterion; CCRIS 7326; EINECS 221-379-0; NSC 21308; n-ethylglutamine; L-Theamine; MFCD00059653; NSC-21308; HSDB 8166; (+)-Theanine; N?-Ethyl-L-glutamine; H-Glu(NHEt)-OH; PubChem13022; N-?-Ethyl-L-glutamine; Spectrum2_001693; Spectrum3_001137; Spectrum4_001984; Spectrum5_000897; Glutamine, N-gamma-ethyl-; Glutamine, N-ethyl-, L-; BSPBio_002633; KBioGR_002514; SCHEMBL190716; SPECTRUM1505254; SPBio_001646; EBD678; CHEMBL3039113; KBio3_002133; DTXSID80184817; L-glutamic acid -r-monoethylamide; L-Theanine, >=98% (HPLC); BCP28252; ZINC1532828; ANW-26983; CCG-38778; CT0238; s3852; AKOS016842508; AM82649; DB12444; L-Theanine (Ngamma-ethyl-L-glutamine); SDCCGMLS-0066811.P001; NCGC00178565-01; AC-23939; AS-12265; HY-15121; AB0006097; CS-0003777; N2085; C01047; 081T616; A820634; Q909931; SR-05000002409; Q-201330; SR-05000002409-1; (2S)-2-azanyl-5-(ethylamino)-5-oxidanylidene-pentanoic acid; C6B5A580-D410-4464-ADB8-543860137D4C; L-Theanine, United States Pharmacopeia (USP) Reference Standard
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Species Origin Theaceae ...     Click to Show/Hide
Theaceae
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Ericales
Family: Theaceae
Disease Attention deficit hyperactivity disorder [ICD-11: 6A05] Phase 2 [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.975
 
MDCK Permeability
 -5.121
 
PAMPA
 +++
 
HIA
 - - -
 
Distribution
VDss
 -0.632
 
PPB
 11.9%
 
BBB
 - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 +++
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 - - -
HLM Stability
 - - -
 
Excretion
CLplasma
 6.905
 
T1/2
 0.933
Toxicity
DILI
 - - -
 
Rat Oral Acute Toxicity
 -
 
FDAMDD
 - - -
 
Respiratory
 - -
 
Human Hepatotoxicity
 -
 
Ototoxicity
 - -
 
Drug-induced Nephrotoxicity
 ++
 
Drug-induced Neurotoxicity
 -
 
Hematotoxicity
 - -
 
Genotoxicity
 ++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C7H14N2O3
PubChem CID
439378
Canonical SMILES
CCNC(=O)CCC(C(=O)O)N
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
CAS Number
CAS 3081-61-6
ChEBI ID
CHEBI:17394
Herb ID
HBIN046248
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model M5076 CVCL_3997 Mouse ovarian histiocytic sarcoma Mus musculus
                    In-vivo Model M5076 ovarian sarcoma (1 * 106 cells/mouse) were s.c. transplanted onto the backs of BDF1 mice.
                    Experimental
                    Result(s)		 Theanine increased not only the antitumor activity on primary tumor but also the metastasis-suppressive efficacy of doxorubicin.
Target and Pathway
Target(s) Interleukin-6 (IL6)  Molecule Info  [3]
KEGG Pathway Cytokine-cytokine receptor interaction Click to Show/Hide
2 HIF-1 signaling pathway
3 FoxO signaling pathway
4 PI3K-Akt signaling pathway
5 Toll-like receptor signaling pathway
6 NOD-like receptor signaling pathway
7 Cytosolic DNA-sensing pathway
8 Jak-STAT signaling pathway
9 Hematopoietic cell lineage
10 TNF signaling pathway
11 Intestinal immune network for IgA production
12 Non-alcoholic fatty liver disease (NAFLD)
13 Prion diseases
14 Salmonella infection
15 Pertussis
16 Legionellosis
17 Chagas disease (American trypanosomiasis)
18 African trypanosomiasis
19 Malaria
20 Amoebiasis
21 Tuberculosis
22 Hepatitis B
23 Measles
24 Influenza A
25 HTLV-I infection
26 Herpes simplex infection
27 Pathways in cancer
28 Transcriptional misregulation in cancer
29 Inflammatory bowel disease (IBD)
30 Rheumatoid arthritis
31 Graft-versus-host disease
32 Hypertrophic cardiomyopathy (HCM)
NetPath Pathway IL1 Signaling Pathway Click to Show/Hide
2 TWEAK Signaling Pathway
3 TCR Signaling Pathway
4 IL2 Signaling Pathway
5 IL4 Signaling Pathway
6 TGF_beta_Receptor Signaling Pathway
7 TNFalpha Signaling Pathway
8 Alpha6Beta4Integrin Signaling Pathway
9 TSLP Signaling Pathway
10 Leptin Signaling Pathway
11 RANKL Signaling Pathway
12 IL5 Signaling Pathway
Panther Pathway Interleukin signaling pathway Click to Show/Hide
Pathway Interaction Database LPA receptor mediated events Click to Show/Hide
2 IL27-mediated signaling events
3 Validated transcriptional targets of AP1 family members Fra1 and Fra2
4 SHP2 signaling
5 Glucocorticoid receptor regulatory network
6 amb2 Integrin signaling
7 ATF-2 transcription factor network
8 AP-1 transcription factor network
9 IL6-mediated signaling events
10 IL23-mediated signaling events
Reactome Interleukin-6 signaling Click to Show/Hide
2 MAPK3 (ERK1) activation
3 MAPK1 (ERK2) activation
4 Senescence-Associated Secretory Phenotype (SASP)
WikiPathways Toll-like receptor signaling pathway Click to Show/Hide
2 SIDS Susceptibility Pathways
3 TCR Signaling Pathway
4 Senescence and Autophagy in Cancer
5 Cytokines and Inflammatory Response
6 IL-6 signaling pathway
7 Myometrial Relaxation and Contraction Pathways
8 Hematopoietic Stem Cell Differentiation
9 Differentiation Pathway
10 Interleukin-6 signaling
11 Spinal Cord Injury
12 Adipogenesis
13 TNF alpha Signaling Pathway
14 TSLP Signaling Pathway
15 TWEAK Signaling Pathway
16 Folate Metabolism
17 Vitamin B12 Metabolism
18 Selenium Micronutrient Network
19 Regulation of toll-like receptor signaling pathway
References
Reference 1 ClinicalTrials.gov (NCT00291070) Effects of L-Theanine in Boys With ADHD
Reference 2 Combination of theanine with doxorubicin inhibits hepatic metastasis of M5076 ovarian sarcoma. Clin Cancer Res. 1999 Feb;5(2):413-6.
Reference 3 Enhancement of postoperative recovery by preoperative oral co-administration of the amino acids, cystine and theanine, in a mouse surgical model. Clin Nutr. 2012 Aug;31(4):555-61.
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