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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-10-29 20:42:12 UTC
HMDB IDHMDB00929
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-Tryptophan
DescriptionTryptophan 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. (http://www.dcnutrition.com).
Structure
Thumb
Synonyms
  1. (-)-tryptophan
  2. (2S)-2-amino-3-(1H-indol-3-yl)propanoate
  3. (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
  4. (L)-tryptophan
  5. (S)-1H-Indole-3-alanine
  6. (S)-2-Amino-3-(3-indolyl)propionic acid
  7. (S)-a-Amino-1H-indole-3-propanoate
  8. (S)-a-Amino-1H-indole-3-propanoic acid
  9. (S)-a-amino-b-indolepropionate
  10. (S)-a-amino-b-indolepropionic acid
  11. (S)-a-Aminoindole-3-propionate
  12. (S)-a-Aminoindole-3-propionic acid
  13. (S)-alpha-Amino-1H-indole-3-propanoate
  14. (S)-alpha-Amino-1H-indole-3-propanoic acid
  15. (S)-alpha-Amino-beta-(3-indolyl)-propionic acid
  16. (S)-alpha-amino-beta-indolepropionate
  17. (S)-alpha-amino-beta-indolepropionic acid
  18. (S)-alpha-Aminoindole-3-propionate
  19. (S)-alpha-Aminoindole-3-propionic acid
  20. (S)-tryptophan
  21. 1-beta-3-Indolylalanine
  22. 1beta-3-Indolylalanine
  23. 1H-Indole-3-Alanine
  24. 2-Amino-3-indolylpropanoate
  25. 2-Amino-3-indolylpropanoic acid
  26. 3-(1H-Indol-3-yl)-L-Alanine
  27. 3-Indol-3-ylalanine
  28. alpha'-Amino-3-indolepropionic acid
  29. alpha-Aminoindole-3-propionic acid
  30. Ardeytropin
  31. H-TRP-oh
  32. Indole-3-alanine
  33. Kalma
  34. L-(-)-Tryptophan
  35. L-alpha-Amino-3-indolepropionic acid
  36. L-alpha-Aminoindole-3-propionic acid
  37. L-b-3-Indolylalanine
  38. L-beta-3-Indolylalanine
  39. L-Tryptofan
  40. L-Tryptophan
  41. L-Tryptophane
  42. Lopac-T-0254
  43. Lyphan
  44. Optimax
  45. Pacitron
  46. Sedanoct
  47. Triptofano
  48. Trofan
  49. Tryptacin
  50. Tryptan
  51. Tryptophan
  52. Tryptophane
  53. Tryptophanum
Chemical FormulaC11H12N2O2
Average Molecular Weight204.2252
Monoisotopic Molecular Weight204.089877638
IUPAC Name(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional NameL-tryptophan
CAS Registry Number73-22-3
SMILES
N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O
InChI Identifier
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
InChI KeyQIVBCDIJIAJPQS-VIFPVBQESA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Common amino acids(KEGG)
  • amino acid zwitterion(ChEBI)
Substituents
  • Carboxylic Acid
  • Indole
  • Indolyl Carboxylic Acid Derivative
  • Primary Aliphatic Amine (Alkylamine)
  • Pyrrole
  • Tryptamine
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Food
Biofunction
  • Component of Aminoacyl-tRNA biosynthesis
  • Component of Histidine metabolism
  • Component of Indole and ipecac alkaloid biosynthesis
  • Component of Phenylalanine metabolism
  • Component of Tryptophan metabolism
  • Component of Tyrosine metabolism
  • Essential amino acid
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point230 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility13.4 mg/mL at 25 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP-1.06HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP-1.1ALOGPS
logP-1.1ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.11ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.2ChemAxon
Polarizability21.05ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Fibroblasts
  • Nerve Cells
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Transcription/TranslationSMP00019Not Available
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified54.5 +/- 9.7 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified78.4 +/- 15.5 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified44.0 (37.0-51.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified48.7 +/- 11.6 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified101.5 +/- 27.2 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified45.0 +/- 9.0 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified5 +/- 3 uMNot SpecifiedBothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.3 +/- 0.4 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified2.32 +/- 0.09 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.25 +/- 0.95 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified20.4 +/- 8.2 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.0 +/- 0.53 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.0 (1.2-2.5) uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified15.9 +/- 4.1 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.64 +/- 0.52 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.5 +/- 0.5 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.46 +/- 0.31 uMAdult (>18 years old)FemaleNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified4.80 +/- 3.41 uMAdult (>18 years old)BothNormal
    • Dame, ZT. et al. ...
details
UrineDetected and Quantified7.8 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.45-29.40 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected and Quantified13.52 +/- 7.37 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified4.62 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Shaykhutdinov RA,...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified5.6 (9.3-2.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified6.3 (3.4-11.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified3.9 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified5.263 (1.316-9.211) umol/mmol creatinineAdult (>18 years old)BothNormal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified83.3 +/- 26.0 uMAdult (>18 years old)MaleSchizophrenia details
    BloodDetected and Quantified80.2 +/- 22.0 uMAdult (>18 years old)FemaleSchizophrenia details
    BloodDetected and Quantified31.6 (29.6-33.6) uMAdult (>18 years old)Both
    Epilepsy
    details
    BloodDetected and Quantified37.2 (34.3-40.1) uMAdult (>18 years old)Both
    Epilepsy
    details
    BloodDetected and Quantified53.3 (50.3-56.3) uMAdult (>18 years old)Both
    Epilepsy
    details
    BloodDetected and Quantified33.06 +/- 8.99 uMAdult (>18 years old)BothAlzheimer's disease details
    Cerebrospinal Fluid (CSF)Detected and Quantified2.035 +/- 0.649 uMAdult (>18 years old)Not Specifiedceliac disease details
    Cerebrospinal Fluid (CSF)Detected and Quantified0.0018 +/- 0.0003 uMAdult (>18 years old)BothHypothyroidism details
    Cerebrospinal Fluid (CSF)Detected and Quantified1.6 +/- 0.3 uMAdult (>18 years old)BothHypothyroidism details
    Cerebrospinal Fluid (CSF)Detected and Quantified1.0 +/- 0.2 uMChildren (1-13 years old)BothHartnup Disease details
    Cerebrospinal Fluid (CSF)Detected and Quantified1.7 +/- 0.27 uMAdult (>18 years old)BothEpilepsy details
    Cerebrospinal Fluid (CSF)Detected and Quantified1.6+/- 0.57 uMAdult (>18 years old)BothEpilepsy details
    Cerebrospinal Fluid (CSF)Detected and Quantified1.7 +/- 0.4 uMAdult (>18 years old)Not SpecifiedEpilepsy details
    Cerebrospinal Fluid (CSF)Detected and Quantified1.68 +/- 0.52 uMAdult (>18 years old)BothEpilepsy details
    Cerebrospinal Fluid (CSF)Detected and Quantified14.3 +/- 12.5 uMAdult (>18 years old)Not SpecifiedEpilepsy details
    Cerebrospinal Fluid (CSF)Detected and Quantified11.5 +/- 8.2 uMAdult (>18 years old)Not SpecifiedEpilepsy details
    Cerebrospinal Fluid (CSF)Detected and Quantified13.0 +/- 5.2 uMChildren (1-13 years old)Not SpecifiedLeukemia details
    Cerebrospinal Fluid (CSF)Detected and Quantified12.8 +/- 3.5 uMChildren (1-13 years old)Not Specified
    Leukemia
    details
    Cerebrospinal Fluid (CSF)Detected and Quantified2.42 +/- 0.14 uMAdult (>18 years old)Not SpecifiedOlivopontocerebellar atrophy (OPCA) details
    Cerebrospinal Fluid (CSF)Detected and Quantified1.80 +/- 0.2 uMAdult (>18 years old)Not SpecifiedAutosomal recessive spastic ataxia of Charlevoix-Saguena details
    Cerebrospinal Fluid (CSF)Detected and Quantified1.8 +/- 0.3 uMAdult (>18 years old)Not SpecifiedHypothyroidism details
    Cerebrospinal Fluid (CSF)Detected and Quantified1.3 +/- 0.32 uMAdult (>18 years old)BothAlzheimer's disease details
    Cerebrospinal Fluid (CSF)Detected and Quantified2.4 +/- 0.13 uMNot SpecifiedNot SpecifiedFriedreich's ataxia details
    Cerebrospinal Fluid (CSF)Detected and Quantified2.67 +/- 0.6 uMAdult (>18 years old)BothSchizophrenia details
    SalivaDetected and Quantified0.22 +/- 0.16 uMAdult (>18 years old)MaleAlzheimer's disease details
    SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothOral cancer details
    SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleBreast cancer details
    SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedPancreatic cancer details
    SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedPeriodontal diseases details
    SalivaDetected and Quantified0.40 +/- 0.21 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
    SalivaDetected and Quantified0.60 +/- 0.49 uMAdult (>18 years old)BothLewy body disease details
    UrineDetected and Quantified7.83 +/- 7.48 umol/mmol creatinineAdult (>18 years old)BothCachexia details
    UrineDetected and Quantified1.19 +/- 0.23 umol/mmol creatinineAdult (>18 years old)BothAlzheimer's disease details
    Associated Disorders and Diseases
    Disease References
    Alzheimer's disease
    1. Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479
    Cachexia
    1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. Pubmed: 18953024
    Epilepsy
    1. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292
    2. Botez MI, Young SN: Effects of anticonvulsant treatment and low levels of folate and thiamine on amine metabolites in cerebrospinal fluid. Brain. 1991 Feb;114 ( Pt 1A):333-48. Pubmed: 1705463
    Schizophrenia
    1. Alfredsson G, Wiesel FA: Monoamine metabolites and amino acids in serum from schizophrenic patients before and during sulpiride treatment. Psychopharmacology (Berl). 1989;99(3):322-7. Pubmed: 2480613
    2. Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. Pubmed: 7595563
    Friedreich's ataxia
    1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. Pubmed: 11383938
    Hartnup disease
    1. Jonas AJ, Butler IJ: Circumvention of defective neutral amino acid transport in Hartnup disease using tryptophan ethyl ester. J Clin Invest. 1989 Jul;84(1):200-4. Pubmed: 2472426
    Hypothyroidism
    1. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. Pubmed: 9849813
    Leukemia
    1. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239
    Olivopontocerebral atrophy
    1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. Pubmed: 11383938
    Hereditary spastic paraplegia
    1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. Pubmed: 11383938
    Associated OMIM IDs
    DrugBank IDDB00150
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB002250
    KNApSAcK IDC00001396
    Chemspider ID6066
    KEGG Compound IDC00078
    BioCyc IDTRP
    BiGG ID33772
    Wikipedia LinkKalma
    NuGOwiki LinkHMDB00929
    Metagene LinkHMDB00929
    METLIN ID5879
    PubChem Compound6305
    PDB IDTRP
    ChEBI ID16828
    References
    Synthesis ReferenceAmir-Heidari, Bagher; Thirlway, Jenny; Micklefield, Jason. Stereochemical course of tryptophan dehydrogenation during biosynthesis of the calcium-dependent lipopeptide antibiotics. Organic Letters (2007), 9(8), 1513-1516.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
    2. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. Pubmed: 9849813
    3. Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. Pubmed: 8884658
    4. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239
    5. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. Pubmed: 12297216
    6. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292
    7. Buczko W, Cylwik D, Stokowska W: [Metabolism of tryptophan via the kynurenine pathway in saliva] Postepy Hig Med Dosw (Online). 2005;59:283-9. Pubmed: 15995595
    8. Heyes MP, Saito K, Crowley JS, Davis LE, Demitrack MA, Der M, Dilling LA, Elia J, Kruesi MJ, Lackner A, et al.: Quinolinic acid and kynurenine pathway metabolism in inflammatory and non-inflammatory neurological disease. Brain. 1992 Oct;115 ( Pt 5):1249-73. Pubmed: 1422788
    9. Koskiniemi M, Laakso J, Kuurne T, Laipio M, Harkonen M: Indole levels in human lumbar and ventricular cerebrospinal fluid and the effect of L-tryptophan administration. Acta Neurol Scand. 1985 Feb;71(2):127-32. Pubmed: 2580417
    10. Jonas AJ, Butler IJ: Circumvention of defective neutral amino acid transport in Hartnup disease using tryptophan ethyl ester. J Clin Invest. 1989 Jul;84(1):200-4. Pubmed: 2472426
    11. Guchhait RB, Janson C, Price WH: Validity of plasma factor in schizophrenia as measured by tryptophan uptake. Biol Psychiatry. 1975 Jun;10(3):303-14. Pubmed: 49200
    12. Kennedy JS, Gwirtsman HE, Schmidt DE, Johnson BW, Fielstein E, Salomon RM, Shiavi RG, Ebert MH, Parris WC, Loosen PT: Serial cerebrospinal fluid tryptophan and 5-hydroxy indoleacetic acid concentrations in healthy human subjects. Life Sci. 2002 Aug 23;71(14):1703-15. Pubmed: 12137916
    13. Bender KI, Lutsevich NF, Lutsevich AN, Kupchikov VV: [Endogenous metabolites as modulators of the transport of drugs by serum albumin] Farmakol Toksikol. 1990 May-Jun;53(3):72-80. Pubmed: 2201566
    14. Heiman-Patterson TD, Bird SJ, Parry GJ, Varga J, Shy ME, Culligan NW, Edelsohn L, Tatarian GT, Heyes MP, Garcia CA, et al.: Peripheral neuropathy associated with eosinophilia-myalgia syndrome. Ann Neurol. 1990 Oct;28(4):522-8. Pubmed: 2174666
    15. Talbert AM, Tranter GE, Holmes E, Francis PL: Determination of drug-plasma protein binding kinetics and equilibria by chromatographic profiling: exemplification of the method using L-tryptophan and albumin. Anal Chem. 2002 Jan 15;74(2):446-52. Pubmed: 11811421
    16. Dunner DL, Heiber S, Perel JM: The effect of L-tryptophan administration on the concentration of probenecid in plasma and cerebrospinal fluid in patients. Psychopharmacology (Berl). 1977 Aug 16;53(3):305-8. Pubmed: 408860
    17. George CF, Millar TW, Hanly PJ, Kryger MH: The effect of L-tryptophan on daytime sleep latency in normals: correlation with blood levels. Sleep. 1989 Aug;12(4):345-53. Pubmed: 2669092
    18. Gutsche B, Grun C, Scheutzow D, Herderich M: Tryptophan glycoconjugates in food and human urine. Biochem J. 1999 Oct 1;343 Pt 1:11-9. Pubmed: 10493906

    Enzymes

    General function:
    Involved in carboxy-lyase activity
    Specific function:
    Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
    Gene Name:
    DDC
    Uniprot ID:
    P20711
    Molecular weight:
    53893.755
    Reactions
    L-Tryptophan → Tryptamine + Carbon dioxidedetails
    References
    1. Tyce GM: Origin and metabolism of serotonin. J Cardiovasc Pharmacol. 1990;16 Suppl 3:S1-7. Pubmed: 1369709
    General function:
    Involved in heme binding
    Specific function:
    Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
    Gene Name:
    IDO1
    Uniprot ID:
    P14902
    Molecular weight:
    45325.89
    Reactions
    L-Tryptophan + Oxygen → L-Formylkynureninedetails
    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: 16887964
    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: 17430109
    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: 16842443
    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: 17417651
    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: 17015752
    6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed: 11752352
    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: 19290871
    General function:
    Involved in amino acid binding
    Specific function:
    Not Available
    Gene Name:
    TPH1
    Uniprot ID:
    P17752
    Molecular weight:
    50984.725
    Reactions
    L-Tryptophan + L-erythro-tetrahydrobiopterin + Oxygen → Oxitriptan + 4a-Hydroxytetrahydrobiopterindetails
    L-erythro-tetrahydrobiopterin + L-Tryptophan + Oxygen → Oxitriptan + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
    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: 16953590
    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: 16897368
    3. Nakamura K, Hasegawa H: Developmental role of tryptophan hydroxylase in the nervous system. Mol Neurobiol. 2007 Feb;35(1):45-54. Pubmed: 17519505
    4. Invernizzi RW: Role of TPH-2 in brain function: news from behavioral and pharmacologic studies. J Neurosci Res. 2007 Nov 1;85(14):3030-5. Pubmed: 17492791
    5. Neckameyer WS, Coleman CM, Eadie S, Goodwin SF: Compartmentalization of neuronal and peripheral serotonin synthesis in Drosophila melanogaster. Genes Brain Behav. 2007 Nov;6(8):756-69. Epub 2007 Mar 21. Pubmed: 17376153
    General function:
    Involved in amino acid binding
    Specific function:
    Not Available
    Gene Name:
    TPH2
    Uniprot ID:
    Q8IWU9
    Molecular weight:
    56056.295
    Reactions
    L-Tryptophan + L-erythro-tetrahydrobiopterin + Oxygen → Oxitriptan + 4a-Hydroxytetrahydrobiopterindetails
    L-erythro-tetrahydrobiopterin + L-Tryptophan + Oxygen → Oxitriptan + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
    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. 2006 Jun 23;. Pubmed: 16806105
    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: 17408646
    3. Nakamura K, Hasegawa H: Developmental role of tryptophan hydroxylase in the nervous system. Mol Neurobiol. 2007 Feb;35(1):45-54. Pubmed: 17519505
    4. Invernizzi RW: Role of TPH-2 in brain function: news from behavioral and pharmacologic studies. J Neurosci Res. 2007 Nov 1;85(14):3030-5. Pubmed: 17492791
    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 Nov;103(3):1111-20. Epub 2007 Jul 31. Pubmed: 17666043
    General function:
    Involved in nucleotide binding
    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
    Reactions
    Adenosine triphosphate + L-Tryptophan + tRNA(Trp) → Adenosine monophosphate + Pyrophosphate + L-tryptophyl-tRNA(Trp)details
    Adenosine triphosphate + L-Tryptophan + tRNA(Trp) → Adenosine monophosphate + Pyrophosphate + L-Tryptophanyl-tRNA(Trp)details
    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: 17150540
    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: 17428498
    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: 17114500
    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: 17661345
    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: 16724112
    General function:
    Involved in nucleotide binding
    Specific function:
    Not Available
    Gene Name:
    WARS2
    Uniprot ID:
    Q9UGM6
    Molecular weight:
    40146.265
    Reactions
    Adenosine triphosphate + L-Tryptophan + tRNA(Trp) → Adenosine monophosphate + Pyrophosphate + L-tryptophyl-tRNA(Trp)details
    Adenosine triphosphate + L-Tryptophan + tRNA(Trp) → Adenosine monophosphate + Pyrophosphate + L-Tryptophanyl-tRNA(Trp)details
    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: 17114825
    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: 17428498
    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: 16639024
    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: 16724112
    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: 16636268
    General function:
    Involved in 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
    Reactions
    L-Tryptophan + Oxygen → L-Formylkynureninedetails
    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: 19290871
    General function:
    Involved in heme binding
    Specific function:
    Catalyzes the first and rate-limiting step in the kynurenine pathway of tryptophan catabolism.
    Gene Name:
    IDO2
    Uniprot ID:
    Q6ZQW0
    Molecular weight:
    47074.745
    Reactions
    L-Tryptophan + Oxygen → L-Formylkynureninedetails
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
    Gene Name:
    IL4I1
    Uniprot ID:
    Q96RQ9
    Molecular weight:
    65327.26
    Reactions
    L-Tryptophan + Water + Oxygen → Indolepyruvate + Ammonia + Hydrogen peroxidedetails

    Transporters

    General function:
    Involved in transmembrane transport
    Specific function:
    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
    Gene Name:
    SLC16A2
    Uniprot ID:
    P36021
    Molecular weight:
    59510.9
    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: 12871948
    General function:
    Involved in transmembrane transport
    Specific function:
    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
    Gene Name:
    SLC16A10
    Uniprot ID:
    Q8TF71
    Molecular weight:
    55492.1
    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: 11827462
    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: 11278508