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Identification
Name L-Tryptophan
Accession Number DB00150 (EXPT02064, NUTR00058)
Type small molecule
Groups approved, nutraceutical
Description

An essential amino acid that is necessary for normal growth in infants and for nitrogen balance in adults. It is a precursor of indole alkaloids in plants. It is a precursor of serotonin (hence its use as an antidepressant and sleep aid). It can be a precursor to niacin, albeit inefficiently, in mammals. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(-)-Tryptophan
(S)-a-Amino-1H-indole-3-propanoic acid
(S)-a-Amino-b-indolepropionic acid
(S)-a-Aminoindole-3-propionic acid
(S)-Tryptophan
2-Amino-3-indolylpropanoic acid
3-Indol-3-ylalanine
alpha-Amino-beta-(3-indolyl)-propionic acid
L-(-)-Tryptophan
l-a-Aminoindole-3-propionic acid
l-b-3-Indolylalanine
L-Tryptophane
Tryptophan
Tryptophane
First Prev Next Last
Salts Not Available
Brand names
Name Company
Alti-Tryptophan
Lyphan
Brand mixtures Not Available
Categories
  • Dietary supplement
  • Micronutrient
  • Essential Amino Acids
  • Antidepressive Agents, Second-Generation
CAS number 73-22-3
Weight Average: 204.2252
Monoisotopic: 204.089877638
Chemical Formula C11H12N2O2
InChI Key InChIKey=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
Plain Text
IUPAC Name
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
SMILES
N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O
Plain Text
Mass Spec show (7.51 KB)
Taxonomy
Kingdom Organic
Classes
  • Amino Acids
  • Tryptamines and Derivatives
Substructures
  • Amino Acids
  • Hydroxy Compounds
  • Acetates
  • Indoles and Indole Derivatives
  • Pyrroles
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Carboxylic Acids and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Tryptamines and Derivatives
Pharmacology
Indication Tryptophan may be useful in increasing serotonin production, promoting healthy sleep, managing depression by enhancing mental and emotional well-being, managing pain tolerance, and managing weight.
Pharmacodynamics Tryptophan is critical for the production of the body's proteins, enzymes and muscle tissue. It is also essential for the production of niacin, the synthesis of the neurotransmitter serotonin and melatonin. Tryptophan supplements can be used as natural relaxants to help relieve insomnia. Tryptophan can also reduce anxiety and depression and has been shown to reduce the intensity of migraine headaches. Other promising indications include the relief of chronic pain, reduction of impulsivity or mania and the treatment of obsessive or compulsive disorders. Tryptophan also appears to help the immune system and can reduce the risk of cardiac spasms. Tryptophan deficiencies may lead to coronary artery spasms. Tryptophan is used as an essential nutrient in infant formulas and intravenous feeding. Tryptophan is marketed as a prescription drug (Tryptan) for those who do not seem to respond well to conventional antidepressants. It may also be used to treat those afflicted with seasonal affective disorder (a winter-onset depression). Tryptopan serves as the precursor for the synthesis of serotonin (5-hydroxytryptamine, 5-HT) and melatonin (N-acetyl-5-methoxytryptamine).
Mechanism of action A number of important side reactions occur during the catabolism of tryptophan on the pathway to acetoacetate. The first enzyme of the catabolic pathway is an iron porphyrin oxygenase that opens the indole ring. The latter enzyme is highly inducible, its concentration rising almost 10-fold on a diet high in tryptophan. Kynurenine is the first key branch point intermediate in the pathway. Kynurenine undergoes deamniation in a standard transamination reaction yielding kynurenic acid. Kynurenic acid and metabolites have been shown to act as antiexcitotoxics and anticonvulsives. A second side branch reaction produces anthranilic acid plus alanine. Another equivalent of alanine is produced further along the main catabolic pathway, and it is the production of these alanine residues that allows tryptophan to be classified among the glucogenic and ketogenic amino acids. The second important branch point converts kynurenine into 2-amino-3-carboxymuconic semialdehyde, which has two fates. The main flow of carbon elements from this intermediate is to glutarate. An important side reaction in liver is a transamination and several rearrangements to produce limited amounts of nicotinic acid, which leads to production of a small amount of NAD+ and NADP+.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Hepatic.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Oral rat LD50: > 16 gm/kg. Investigated as a tumorigen, mutagen, reproductive effector. Symptoms of overdose include agitation, confusion, diarrhea, fever, overactive reflexes, poor coordination, restlessness, shivering, sweating, talking or acting with excitement you cannot control, trembling or shaking, twitching, and vomiting.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Tablet Oral
Prices
Unit description Cost Unit
Tryptan 1 g Tablet 1.6 USD tablet
Tryptan 750 mg Tablet 1.2 USD tablet
Apo-Tryptophan 1 g Tablet 0.9 USD tablet
Ratio-Tryptophan 1 g Tablet 0.9 USD tablet
Tryptan 500 mg Capsule 0.8 USD capsule
Tryptan 500 mg Tablet 0.8 USD tablet
L-tryptophan crystals 0.72 USD g
Apo-Tryptophan 500 mg Capsule 0.45 USD capsule
Apo-Tryptophan 500 mg Tablet 0.45 USD tablet
Pms-Tryptophan 500 mg Capsule 0.45 USD capsule
Pms-Tryptophan 500 mg Tablet 0.45 USD tablet
Ratio-Tryptophan 500 mg Capsule 0.45 USD capsule
Ratio-Tryptophan 500 mg Tablet 0.45 USD tablet
Tryptan 250 mg Tablet 0.4 USD tablet
L-tryptophan 500 mg capsule 0.33 USD capsule
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 290.5 dec °C PhysProp
water solubility 1.34E+004 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP -1.06 HANSCH,C ET AL. (1995)
logS -1.23 ADME Research, USCD
pKa 7.38 (at 25 °C) KORTUM,G ET AL (1961)
Predicted Properties
Property Value Source
water solubility 1.36e+00 g/l ALOGPS
logP -1.1 ALOGPS
logP -1.1 ChemAxon
logS -2.2 ALOGPS
pKa (strongest acidic) 2.54 ChemAxon
pKa (strongest basic) 9.4 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 79.11 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 56.2 ChemAxon
polarizability 21.05 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00020 Link_out
KEGG Compound C00078 Link_out
PubChem Compound 6305 Link_out
PubChem Substance 46508329 Link_out
ChemSpider 6066 Link_out
BindingDB 21974 Link_out
ChEBI 16828 Link_out
ChEMBL 16828 Link_out
Therapeutic Targets Database DAP001316 Link_out
PharmGKB PA10323 Link_out
IUPHAR 717 Link_out
Guide to Pharmacology 717 Link_out
HET TRP Link_out
ATC Codes
  • N06AX02
AHFS Codes
  • 28:16.04.92
PDB Entries
FDA label Not Available
MSDS show (71.7 KB)
Interactions
Drug Interactions
Drug Interaction
Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Isocarboxazid Possible severe adverse reaction with this combination
Vilazodone Due to risks of enhanced serotonin activity and/or adverse reactions (e.g., serotonin syndrome), concomitant use of selective serotonin reuptake inhibitors (SSRIs) and tryptophan is not recommended. Avoid combination.
Zolmitriptan Use of two serotonin modulators, such as zolmitriptan and L-tryptophan, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
Food Interactions Not Available
Targets

1. Tryptophanyl-tRNA synthetase, mitochondrial

Pharmacological action: unknown
Actions: inhibitor

ATP + L-tryptophan + tRNA(Trp) = AMP + diphosphate + L-tryptophyl-tRNA(Trp)

Organism class: human
UniProt ID: Q9UGM6 Link_out
Gene: WARS2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Paley EL, Denisova G, Sokolova O, Posternak N, Wang X, Brownell AL: Tryptamine Induces Tryptophanyl-tRNA Synthetase-Mediated Neurodegeneration With Neurofibrillary Tangles in Human Cell and Mouse Models. Neuromolecular Med. 2007;9(1):55-82. Pubmed
  2. 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. Pubmed
  3. Banin E, Dorrell MI, Aguilar E, Ritter MR, Aderman CM, Smith AC, Friedlander J, Friedlander M: T2-TrpRS inhibits preretinal neovascularization and enhances physiological vascular regrowth in OIR as assessed by a new method of quantification. Invest Ophthalmol Vis Sci. 2006 May;47(5):2125-34. Pubmed
  4. Yang XL, Otero FJ, Ewalt KL, Liu J, Swairjo MA, Kohrer C, RajBhandary UL, Skene RJ, McRee DE, Schimmel P: Two conformations of a crystalline human tRNA synthetase-tRNA complex: implications for protein synthesis. EMBO J. 2006 Jun 21;25(12):2919-29. Epub 2006 May 25. Pubmed
  5. Charriere F, Helgadottir S, Horn EK, Soll D, Schneider A: Dual targeting of a single tRNA(Trp) requires two different tryptophanyl-tRNA synthetases in Trypanosoma brucei. Proc Natl Acad Sci U S A. 2006 May 2;103(18):6847-52. Epub 2006 Apr 24. Pubmed

2. Tryptophanyl-tRNA synthetase

Pharmacological action: unknown
Actions: inhibitor

ATP + L-tryptophan + tRNA(Trp) = AMP + diphosphate + L-tryptophyl-tRNA(Trp)

Organism class: bacterial
UniProt ID: P00953 Link_out
Gene: trpS
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. 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. Pubmed
  4. Kovaleva GK, Favorova OO, Moroz SG, Krauspe R, Kiselev LL: [Active intermediate compound of tryptophanyl-tRNA-synthetase with tryptophan] Dokl Akad Nauk SSSR. 1976;229(2):492-5. Pubmed
  5. Kovaleva GK, Degtiarev SKh, Favorova OO: [Affinity modification of tryptophanyl-tRNA synthetase by an alkylating L-tryptophan analog] Mol Biol (Mosk). 1979 Nov-Dec;13(6):1237-46. Pubmed

3. Tryptophanyl-tRNA synthetase, cytoplasmic

Pharmacological action: unknown
Actions: inhibitor
Organism class: human
UniProt ID: P23381 Link_out
Gene: WARS Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed
  2. 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. Pubmed
  3. Zhu L, Ji F, Wang Y, Zhang Y, Liu Q, Zhang JZ, Matsushima K, Cao Q, Zhang Y: Synovial autoreactive T cells in rheumatoid arthritis resist IDO-mediated inhibition. J Immunol. 2006 Dec 1;177(11):8226-33. Pubmed
  4. Yadav MC, Burudi EM, Alirezaei M, Flynn CC, Watry DD, Lanigan CM, Fox HS: IFN-gamma-induced IDO and WRS expression in microglia is differentially regulated by IL-4. Glia. 2007 Oct;55(13):1385-96. Pubmed
  5. Yang XL, Otero FJ, Ewalt KL, Liu J, Swairjo MA, Kohrer C, RajBhandary UL, Skene RJ, McRee DE, Schimmel P: Two conformations of a crystalline human tRNA synthetase-tRNA complex: implications for protein synthesis. EMBO J. 2006 Jun 21;25(12):2919-29. Epub 2006 May 25. Pubmed
Enzymes

1. Tryptophan 2,3-dioxygenase

Actions: substrate

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)

UniProt ID: P48775 Link_out
Gene: TDO2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Rafice SA, Chauhan N, Efimov I, Basran J, Raven EL: Oxidation of L-tryptophan in biology: a comparison between tryptophan 2,3-dioxygenase and indoleamine 2,3-dioxygenase. Biochem Soc Trans. 2009 Apr;37(Pt 2):408-12. Pubmed

2. Aromatic-L-amino-acid decarboxylase

Actions: substrate

Catalyzes the decarboxylation of L-3,4- dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine

UniProt ID: P20711 Link_out
Gene: DDC Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Tyce GM: Origin and metabolism of serotonin. J Cardiovasc Pharmacol. 1990;16 Suppl 3:S1-7. Pubmed

3. Tryptophanyl-tRNA synthetase

Actions: substrate, inhibitor

ATP + L-tryptophan + tRNA(Trp) = AMP + diphosphate + L-tryptophyl-tRNA(Trp)

UniProt ID: P00953 Link_out
Gene: trpS
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. 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. Pubmed
  4. Kovaleva GK, Favorova OO, Moroz SG, Krauspe R, Kiselev LL: [Active intermediate compound of tryptophanyl-tRNA-synthetase with tryptophan] Dokl Akad Nauk SSSR. 1976;229(2):492-5. Pubmed
  5. Kovaleva GK, Degtiarev SKh, Favorova OO: [Affinity modification of tryptophanyl-tRNA synthetase by an alkylating L-tryptophan analog] Mol Biol (Mosk). 1979 Nov-Dec;13(6):1237-46. Pubmed

4. Tryptophanyl-tRNA synthetase, mitochondrial

Actions: substrate, inhibitor

ATP + L-tryptophan + tRNA(Trp) = AMP + diphosphate + L-tryptophyl-tRNA(Trp)

UniProt ID: Q9UGM6 Link_out
Gene: WARS2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Paley EL, Denisova G, Sokolova O, Posternak N, Wang X, Brownell AL: Tryptamine Induces Tryptophanyl-tRNA Synthetase-Mediated Neurodegeneration With Neurofibrillary Tangles in Human Cell and Mouse Models. Neuromolecular Med. 2007;9(1):55-82. Pubmed
  2. 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. Pubmed
  3. Banin E, Dorrell MI, Aguilar E, Ritter MR, Aderman CM, Smith AC, Friedlander J, Friedlander M: T2-TrpRS inhibits preretinal neovascularization and enhances physiological vascular regrowth in OIR as assessed by a new method of quantification. Invest Ophthalmol Vis Sci. 2006 May;47(5):2125-34. Pubmed
  4. Yang XL, Otero FJ, Ewalt KL, Liu J, Swairjo MA, Kohrer C, RajBhandary UL, Skene RJ, McRee DE, Schimmel P: Two conformations of a crystalline human tRNA synthetase-tRNA complex: implications for protein synthesis. EMBO J. 2006 Jun 21;25(12):2919-29. Epub 2006 May 25. Pubmed
  5. Charriere F, Helgadottir S, Horn EK, Soll D, Schneider A: Dual targeting of a single tRNA(Trp) requires two different tryptophanyl-tRNA synthetases in Trypanosoma brucei. Proc Natl Acad Sci U S A. 2006 May 2;103(18):6847-52. Epub 2006 Apr 24. Pubmed

5. Tryptophan 5-hydroxylase 1

Actions: substrate
UniProt ID: P17752 Link_out
Gene: TPH1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Pavon JA, Fitzpatrick PF: Insights into the catalytic mechanisms of phenylalanine and tryptophan hydroxylase from kinetic isotope effects on aromatic hydroxylation. Biochemistry. 2006 Sep 12;45(36):11030-7. Pubmed
  2. Langfort J, Baranczuk E, Pawlak D, Chalimoniuk M, Lukacova N, Marsala J, Gorski J: The effect of endurance training on regional serotonin metabolism in the brain during early stage of detraining period in the female rat. Cell Mol Neurobiol. 2006 Oct-Nov;26(7-8):1327-42. Epub 2006 Aug 1. Pubmed
  3. Nakamura K, Hasegawa H: Developmental role of tryptophan hydroxylase in the nervous system. Mol Neurobiol. 2007 Feb;35(1):45-54. Pubmed
  4. Invernizzi RW: Role of TPH-2 in brain function: News from behavioral and pharmacologic studies. J Neurosci Res. 2007 May 10;. Pubmed
  5. Neckameyer WS, Coleman CM, Eadie S, Goodwin SF: Compartmentalization of neuronal and peripheral serotonin synthesis in Drosophila melanogaster. Genes Brain Behav. 2007 Mar 21;. Pubmed

6. Tryptophan 5-hydroxylase 2

Actions: substrate
UniProt ID: Q8IWU9 Link_out
Gene: TPH2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Lopez VA, Detera-Wadleigh S, Cardona I, Kassem L, McMahon FJ: Nested association between genetic variation in tryptophan hydroxylase II, bipolar affective disorder, and suicide attempts. Biol Psychiatry. 2007 Jan 15;61(2):181-6. Epub 2006 Jun 27. Pubmed
  2. Kraus MR, Al-Taie O, Schafer A, Pfersdorff M, Lesch KP, Scheurlen M: Serotonin-1A receptor gene HTR1A variation predicts interferon-induced depression in chronic hepatitis C. Gastroenterology. 2007 Apr;132(4):1279-86. Epub 2007 Feb 25. Pubmed
  3. Nakamura K, Hasegawa H: Developmental role of tryptophan hydroxylase in the nervous system. Mol Neurobiol. 2007 Feb;35(1):45-54. Pubmed
  4. Invernizzi RW: Role of TPH-2 in brain function: News from behavioral and pharmacologic studies. J Neurosci Res. 2007 May 10;. Pubmed
  5. Calcagno E, Canetta A, Guzzetti S, Cervo L, Invernizzi RW: Strain differences in basal and post-citalopram extracellular 5-HT in the mouse medial prefrontal cortex and dorsal hippocampus: relation with tryptophan hydroxylase-2 activity. J Neurochem. 2007 Jul 31;. Pubmed

7. Tryptophanyl-tRNA synthetase, cytoplasmic

Actions: substrate, inhibitor
UniProt ID: P23381 Link_out
Gene: WARS Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed
  2. 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. Pubmed
  3. Zhu L, Ji F, Wang Y, Zhang Y, Liu Q, Zhang JZ, Matsushima K, Cao Q, Zhang Y: Synovial autoreactive T cells in rheumatoid arthritis resist IDO-mediated inhibition. J Immunol. 2006 Dec 1;177(11):8226-33. Pubmed
  4. Yadav MC, Burudi EM, Alirezaei M, Flynn CC, Watry DD, Lanigan CM, Fox HS: IFN-gamma-induced IDO and WRS expression in microglia is differentially regulated by IL-4. Glia. 2007 Oct;55(13):1385-96. Pubmed
  5. Yang XL, Otero FJ, Ewalt KL, Liu J, Swairjo MA, Kohrer C, RajBhandary UL, Skene RJ, McRee DE, Schimmel P: Two conformations of a crystalline human tRNA synthetase-tRNA complex: implications for protein synthesis. EMBO J. 2006 Jun 21;25(12):2919-29. Epub 2006 May 25. Pubmed

8. Indoleamine 2,3-dioxygenase

Actions: substrate

Tryptophan degradation

UniProt ID: P14902 Link_out
Gene: INDO Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Agaugue S, Perrin-Cocon L, Coutant F, Andre P, Lotteau V: 1-Methyl-tryptophan can interfere with TLR signaling in dendritic cells independently of IDO activity. J Immunol. 2006 Aug 15;177(4):2061-71. Pubmed
  2. Fallarino F, Gizzi S, Mosci P, Grohmann U, Puccetti P: Tryptophan catabolism in IDO+ plasmacytoid dendritic cells. Curr Drug Metab. 2007 Apr;8(3):209-16. Pubmed
  3. Cozzi A, Zignego AL, Carpendo R, Biagiotti T, Aldinucci A, Monti M, Giannini C, Rosselli M, Laffi G, Moroni F: Low serum tryptophan levels, reduced macrophage IDO activity and high frequency of psychopathology in HCV patients. J Viral Hepat. 2006 Jun;13(6):402-8. Pubmed
  4. Grohmann U, Volpi C, Fallarino F, Bozza S, Bianchi R, Vacca C, Orabona C, Belladonna ML, Ayroldi E, Nocentini G, Boon L, Bistoni F, Fioretti MC, Romani L, Riccardi C, Puccetti P: Reverse signaling through GITR ligand enables dexamethasone to activate IDO in allergy. Nat Med. 2007 May;13(5):579-86. Epub 2007 Apr 8. Pubmed
  5. Zheng X, Koropatnick J, Li M, Zhang X, Ling F, Ren X, Hao X, Sun H, Vladau C, Franek JA, Feng B, Urquhart BL, Zhong R, Freeman DJ, Garcia B, Min WP: Reinstalling antitumor immunity by inhibiting tumor-derived immunosuppressive molecule IDO through RNA interference. J Immunol. 2006 Oct 15;177(8):5639-46. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  7. Rafice SA, Chauhan N, Efimov I, Basran J, Raven EL: Oxidation of L-tryptophan in biology: a comparison between tryptophan 2,3-dioxygenase and indoleamine 2,3-dioxygenase. Biochem Soc Trans. 2009 Apr;37(Pt 2):408-12. Pubmed
Transporters

1. Monocarboxylate transporter 8

Actions: inhibitor

Very active and specific thyroid hormone transporter. Stimulates cellular uptake of thyroxine (T4), triiodothyronine (T3), reverse triiodothyronine (rT3) and diidothyronine. Does not transport Leu, Phe, Trp or Tyr

UniProt ID: P36021 Link_out
Gene: SLC16A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Friesema EC, Ganguly S, Abdalla A, Manning Fox JE, Halestrap AP, Visser TJ: Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter. J Biol Chem. 2003 Oct 10;278(41):40128-35. Epub 2003 Jul 18. Pubmed

2. Monocarboxylate transporter 10

Actions: inhibitor

Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity)

UniProt ID: Q8TF71 Link_out
Gene: SLC16A10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kim DK, Kanai Y, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H: The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan;79(1):95-103. Pubmed
  2. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19