L-Tryptophan
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Basic Info
| Common Name | L-Tryptophan(F05362) |
| 2D Structure | |
| Description | Tryptophan is an essential amino acid which is the precursor of serotonin. Serotonin is a brain neurotransmitter, platelet clotting factor and neurohormone found in organs throughout the body. Metabolism of tryptophan to serotonin requires nutrients such as vitamin B6, niacin and glutathione. Niacin is an important metabolite of tryptophan. High corn or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea and dementia. Inborn errors of tryptophan metabolism exist where a tumor (carcinoid) makes excess serotonin. Hartnup's disease is a disease where tryptophan and other amino acids are not absorbed properly. Tryptophan supplements may be useful in each condition, in carcinoid replacing the over-metabolized nutrient and in Hartnup's supplementing a malabsorbed nutrient. Some disorders of excess tryptophan in the blood may contribute to mental retardation. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan fragments correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension and anxiety states. The requirement for tryptophan and protein decreases with age. Adults' minimum daily requirement is 3 mg/kg/day or about 200 mg a day. This may be an underestimation, for there are 400 mg of tryptophan in just a cup of wheat germ. A cup of low fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg per pound. |
| FRCD ID | F05362 |
| CAS Number | 73-22-3 |
| PubChem CID | 6305 |
| Formula | C11H12N2O2 |
| IUPAC Name | (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid |
| InChI Key | QIVBCDIJIAJPQS-VIFPVBQESA-N |
| InChI | InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1 |
| Canonical SMILES | C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)N |
| Isomeric SMILES | C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)O)N |
| Wikipedia | L-Tryptophan |
| Synonyms |
(S)-Tryptophan
L-tryptophan
tryptophan
73-22-3
L-Tryptophane
Tryptophane
h-Trp-oh
Optimax
trofan
tryptacin
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Indoles and derivatives |
| Subclass | Indolyl carboxylic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Indolyl carboxylic acids and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Indolyl carboxylic acid derivative - Alpha-amino acid - Alpha-amino acid or derivatives - L-alpha-amino acid - 3-alkylindole - Indole - Aralkylamine - Benzenoid - Substituted pyrrole - Heteroaromatic compound - Pyrrole - Amino acid or derivatives - Amino acid - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Azacycle - Amine - Primary aliphatic amine - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organonitrogen compound - Organooxygen compound - Primary amine - Organopnictogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 204.229 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Complexity | 245 |
| Monoisotopic Mass | 204.09 |
| Exact Mass | 204.09 |
| XLogP | -1.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9510 |
| Human Intestinal Absorption | HIA+ | 0.9840 |
| Caco-2 Permeability | Caco2- | 0.5943 |
| P-glycoprotein Substrate | Non-substrate | 0.5988 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9951 |
| Non-inhibitor | 0.9779 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8805 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.3925 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8463 |
| CYP450 2D6 Substrate | Non-substrate | 0.7897 |
| CYP450 3A4 Substrate | Non-substrate | 0.7841 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9531 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9481 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9307 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9644 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9432 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9542 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9864 |
| Non-inhibitor | 0.9402 | |
| AMES Toxicity | Non AMES toxic | 0.9284 |
| Carcinogens | Non-carcinogens | 0.9310 |
| Fish Toxicity | High FHMT | 0.6819 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6688 |
| Honey Bee Toxicity | Low HBT | 0.6838 |
| Biodegradation | Not ready biodegradable | 0.8348 |
| Acute Oral Toxicity | IV | 0.6272 |
| Carcinogenicity (Three-class) | Non-required | 0.7121 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.2926 | LogS |
| Caco-2 Permeability | 0.1091 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.1785 | LD50, mol/kg |
| Fish Toxicity | 2.1566 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.3419 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Peak AAA fatty acid homolog contaminants present in the dietary supplement l-Tryptophan associated with the onset of eosinophilia-myalgia syndrome. | Toxicol Lett | 2018 Sep 15 | 29800716 |
| Self-Assembled Binuclear Cu(II)-Histidine Complex for Absolute Configuration and Enantiomeric Excess Determination of Naproxen by Tandem Mass Spectrometry. | Anal Chem | 2018 Mar 20 | 29455521 |
| Supplementing phytogenic compounds or autolyzed yeast modulates ruminal biogenic amines and plasma metabolome in dry cows experiencing subacute ruminal acidosis. | J Dairy Sci | 2018 Jul 18 | 30031584 |
| Rapid detection of the neonicotinoid insecticide imidacloprid using a quenchbody assay. | Anal Bioanal Chem | 2018 Jul | 29704031 |
| Structure determination of disease associated peak AAA from l-Tryptophanimplicated in the eosinophilia-myalgia syndrome. | Toxicol Lett | 2018 Jan 5 | 29037509 |
| Short communication: Supplementation of colostrum and milk with5-hydroxy-l-tryptophan affects immune factors but not growth performance innewborn calves. | J Dairy Sci | 2018 Jan | 29102139 |
| Interaction of manganese nanoparticle with cytochrome c: A multi-spectroscopicstudy. | Int J Biol Macromol | 2018 Jan | 28818722 |
| Comprehensive Dissection of Metabolic Changes in Albino and Green Tea Cultivars. | J Agric Food Chem | 2018 Feb 28 | 29397711 |
| Protein nutritional value, polyphenols and antioxidant properties of cornfermented with Agaricus brasiliensis and Agaricus bisporus. | World J Microbiol Biotechnol | 2018 Feb 15 | 29450660 |
| Relationships between body temperatures and inflammation indicators under physiological and pathophysiological conditions in pigs exposed to systemic lipopolysaccharide and dietary deoxynivalenol. | J Anim Physiol Anim Nutr (Berl) | 2018 Feb | 28262996 |
| Development of an optical sensor for chlortetracycline detection based on thefluorescence quenching of l-tryptophan. | Luminescence | 2018 Feb | 28929575 |
| Antimicrobial peptides: an effective approach to prevent bacterial biofilmformation in platelet concentrates. | Transfusion | 2018 Apr 24 | 29687885 |
| Effects of tryptophan-containing peptides on angiotensin-converting enzymeactivity and vessel tone ex vivo and in vivo. | Eur J Nutr | 2018 Apr | 28102435 |
| Biotechnological production of aromatic compounds of the extended shikimatepathway from renewable biomass. | J Biotechnol | 2017 Sep 10 | 27871872 |
| Comprehensive study on the effects of sodium and potassium additives in sizeexclusion chromatographic separations of protein biopharmaceuticals. | J Pharm Biomed Anal | 2017 Sep 10 | 27697310 |
| Examining the effect of dietary electrolyte balance, energy source, and length offeeding of nitrogen-free diets on ileal endogenous amino acid losses in broilers. | Poult Sci | 2017 Sep 1 | 28854743 |
| Potential tracers for tracking septic tank effluent discharges in watercourses. | Environ Pollut | 2017 Sep | 28550797 |
| Tryptophan and Cysteine Oxidation Products Dominate in α-Lactalbumin-DerivedPeptides Analyzed with LC-MSn. | J Food Sci | 2017 Sep | 28796377 |
| Antibiotic Treatment Preventing Necrotising Enterocolitis Alters Urinary andPlasma Metabolomes in Preterm Pigs. | J Proteome Res | 2017 Oct 6 | 28871782 |
| Tryptophan-Containing Cyclic Decapeptides with Activity against Plant Pathogenic Bacteria. | Molecules | 2017 Oct 26 | 29072606 |
Targets
- General Function:
- Tryptophan-trna ligase activity
- Specific Function:
- Isoform 1, isoform 2 and T1-TrpRS have aminoacylation activity while T2-TrpRS lacks it. Isoform 2, T1-TrpRS and T2-TrpRS possess angiostatic activity whereas isoform 1 lacks it. T2-TrpRS inhibits fluid shear stress-activated responses of endothelial cells. Regulates ERK, Akt, and eNOS activation pathways that are associated with angiogenesis, cytoskeletal reorganization and shear stress-responsive gene expression.
- Gene Name:
- WARS
- Uniprot ID:
- P23381
- Molecular Weight:
- 53164.91 Da
References
- Tsuchiya W, Umehara T, Kuno A, Hasegawa T: Determination of tryptophan tRNA recognition sites for tryptophanyl-tRNA synthetase from hyperthermophilic archaeon, Aeropyrum pernix K1. Nucleic Acids Symp Ser (Oxf). 2004;(48):185-6. [17150540 ]
- General Function:
- Tryptophan-trna ligase activity
- Gene Name:
- WARS2
- Uniprot ID:
- Q9UGM6
- Molecular Weight:
- 40146.265 Da
References
- Retailleau P, Weinreb V, Hu M, Carter CW Jr: Crystal structure of tryptophanyl-tRNA synthetase complexed with adenosine-5' tetraphosphate: evidence for distributed use of catalytic binding energy in amino acid activation by class I aminoacyl-tRNA synthetases. J Mol Biol. 2007 May 25;369(1):108-28. Epub 2007 Mar 12. [17428498 ]
- General Function:
- Pyrophosphatase activity
- Specific Function:
- This isozyme may play a role in skeletal mineralization.
- Gene Name:
- ALPL
- Uniprot ID:
- P05186
- Molecular Weight:
- 57304.435 Da
References
- Lanier M, Sergienko E, Simao AM, Su Y, Chung T, Millan JL, Cashman JR: Design and synthesis of selective inhibitors of placental alkaline phosphatase. Bioorg Med Chem. 2010 Jan 15;18(2):573-9. doi: 10.1016/j.bmc.2009.12.012. Epub 2009 Dec 11. [20031422 ]
- General Function:
- Zinc ion binding
- Gene Name:
- ALPI
- Uniprot ID:
- P09923
- Molecular Weight:
- 56811.695 Da
References
- Lanier M, Sergienko E, Simao AM, Su Y, Chung T, Millan JL, Cashman JR: Design and synthesis of selective inhibitors of placental alkaline phosphatase. Bioorg Med Chem. 2010 Jan 15;18(2):573-9. doi: 10.1016/j.bmc.2009.12.012. Epub 2009 Dec 11. [20031422 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Can degrade fibronectin, laminin, gelatins of type I, III, IV, and V; collagens III, IV, X, and IX, and cartilage proteoglycans. Activates procollagenase.
- Gene Name:
- MMP3
- Uniprot ID:
- P08254
- Molecular Weight:
- 53976.84 Da
References
- Ye QZ, Johnson LL, Nordan I, Hupe D, Hupe L: A recombinant human stromelysin catalytic domain identifying tryptophan derivatives as human stromelysin inhibitors. J Med Chem. 1994 Jan 7;37(1):206-9. [8289198 ]
- General Function:
- Tryptophan 2,3-dioxygenase activity
- Specific Function:
- Incorporates oxygen into the indole moiety of tryptophan. Has a broad specificity towards tryptamine and derivatives including D- and L-tryptophan, 5-hydroxytryptophan and serotonin (By similarity).
- Gene Name:
- TDO2
- Uniprot ID:
- P48775
- Molecular Weight:
- 47871.215 Da
References
- Dolusic E, Larrieu P, Moineaux L, Stroobant V, Pilotte L, Colau D, Pochet L, Van den Eynde B, Masereel B, Wouters J, Frederick R: Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators. J Med Chem. 2011 Aug 11;54(15):5320-34. doi: 10.1021/jm2006782. Epub 2011 Jul 18. [21726069 ]
- General Function:
- Phospholipase a2 activator activity
- Specific Function:
- Involved in the maintenance of ubiquitin levels.
- Gene Name:
- PLAA
- Uniprot ID:
- Q9Y263
- Molecular Weight:
- 87156.21 Da
References
- Lanier M, Sergienko E, Simao AM, Su Y, Chung T, Millan JL, Cashman JR: Design and synthesis of selective inhibitors of placental alkaline phosphatase. Bioorg Med Chem. 2010 Jan 15;18(2):573-9. doi: 10.1016/j.bmc.2009.12.012. Epub 2009 Dec 11. [20031422 ]