Human Metabolome Database Version 3.5

Showing metabocard for L-Tryptophan (HMDB00929)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:36 -0700
HMDB ID HMDB00929
Secondary Accession Numbers None
Metabolite Identification
Common Name L-Tryptophan
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. (http://www.dcnutrition.com).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C11H12N2O2
Average Molecular Weight 204.2252
Monoisotopic Molecular Weight 204.089877638
IUPAC Name (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional IUPAC Name L-tryptophan
CAS Registry Number 73-22-3
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 Key QIVBCDIJIAJPQS-VIFPVBQESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha 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 Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected 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
Application Not Available
Cellular locations
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 230 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 13.4 mg/mL at 25 °C YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP -1.06 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 1.36 g/L ALOGPS
LogP -1.10 ALOGPS
LogP -1.1 ChemAxon
LogS -2.18 ALOGPS
pKa (strongest acidic) 2.54 ChemAxon
pKa (strongest basic) 9.4 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 79.11 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 56.2 ChemAxon
Polarizability 21.05 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Fibroblasts
  • Prostate
  • Nerve Cells
Pathways
Name SMPDB Link KEGG Link
Tryptophan Metabolism SMP00063 map00380 Link_out
Transcription/Translation SMP00019 Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
54.5 +/- 9.7 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
78.4 +/- 15.5 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
44.0 (37.0-51.0) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
48.7 +/- 11.6 uM Adult (>18 years old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
101.5 +/- 27.2 uM Newborn (0-30 days old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
45.0 +/- 9.0 uM Adult (>18 years old) Male Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
5 +/- 3 uM Not Specified Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
1.3 +/- 0.4 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
2.32 +/- 0.09 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
2.25 +/- 0.95 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
20.4 +/- 8.2 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
2.0 +/- 0.53 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
2.0 (1.2-2.5) uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
15.9 +/- 4.1 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
2.64 +/- 0.52 uM Adult (>18 years old) Both Normal
Saliva Detected and Quantified
0.5 +/- 0.5 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
7.8 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
2.45-29.40 umol/mmol creatinine Adult (>18 years old) Both Normal
  • David F. Put...
Urine Detected and Quantified
13.52 +/- 7.37 umol/mmol creatinine Infant (0-1 year old) Both Normal
Urine Detected and Quantified
4.62 umol/mmol creatinine Adult (>18 years old) Both Normal
  • Shaykhutdino...
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
5.6 (9.3-2.1) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
6.3 (3.4-11.1) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
3.9 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
5.263 (1.316-9.211) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 83.3 +/- 26.0 uM Adult (>18 years old) Male Schizophrenia
Blood Detected and Quantified 80.2 +/- 22.0 uM Adult (>18 years old) Female Schizophrenia
Blood Detected and Quantified 31.6 (29.6-33.6) uM Adult (>18 years old) Both Comment Epilepsy
Blood Detected and Quantified 37.2 (34.3-40.1) uM Adult (>18 years old) Both Comment Epilepsy
Blood Detected and Quantified 53.3 (50.3-56.3) uM Adult (>18 years old) Both Comment Epilepsy
Blood Detected and Quantified 33.06 +/- 8.99 uM Adult (>18 years old) Both Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 2.035 +/- 0.649 uM Adult (>18 years old) Not Specified celiac disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0018 +/- 0.0003 uM Adult (>18 years old) Both Hypothyroidism
Cerebrospinal Fluid (CSF) Detected and Quantified 1.6 +/- 0.3 uM Adult (>18 years old) Both Hypothyroidism
Cerebrospinal Fluid (CSF) Detected and Quantified 1.0 +/- 0.2 uM Children (1-13 year old) Both Hartnup Disease
Cerebrospinal Fluid (CSF) Detected and Quantified 1.7 +/- 0.27 uM Adult (>18 years old) Both Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 1.6+/- 0.57 uM Adult (>18 years old) Both Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 1.7 +/- 0.4 uM Adult (>18 years old) Not Specified Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 1.68 +/- 0.52 uM Adult (>18 years old) Both Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 14.3 +/- 12.5 uM Adult (>18 years old) Not Specified Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 11.5 +/- 8.2 uM Adult (>18 years old) Not Specified Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 13.0 +/- 5.2 uM Children (1-13 year old) Not Specified Leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 12.8 +/- 3.5 uM Children (1-13 year old) Not Specified Comment Leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 2.42 +/- 0.14 uM Adult (>18 years old) Not Specified Olivopontocerebellar atrophy (OPCA)
Cerebrospinal Fluid (CSF) Detected and Quantified 1.80 +/- 0.2 uM Adult (>18 years old) Not Specified Spastic Ataxia
Cerebrospinal Fluid (CSF) Detected and Quantified 1.8 +/- 0.3 uM Adult (>18 years old) Not Specified Hypothyroidism
Cerebrospinal Fluid (CSF) Detected and Quantified 1.3 +/- 0.32 uM Adult (>18 years old) Both Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 2.4 +/- 0.13 uM Not Specified Not Specified Friedreich's ataxia
Cerebrospinal Fluid (CSF) Detected and Quantified 2.67 +/- 0.6 uM Adult (>18 years old) Both Schizophrenia
Urine Detected and Quantified 7.83 +/- 7.48 umol/mmol creatinine Adult (>18 years old) Both Cachexia
Urine Detected and Quantified 1.19 +/- 0.23 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease
Associated Disorders and Diseases
Disease References
Cachexia
  • 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 Link_out
      Epilepsy
      • 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 Link_out
      • 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 Link_out
          Hartnup disease
          • 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 Link_out
              Leukemia
              • 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 Link_out
                  Olivopontocerebral atrophy
                  • 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 Link_out
                      Hereditary spastic paraplegia
                      • 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 Link_out
                          Hypothyroidism
                          • 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 Link_out
                              Friedreich's ataxia
                              • 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 Link_out
                                  Schizophrenia
                                  • 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 Link_out
                                  • 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 Link_out
                                      Alzheimer's disease
                                      • 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 Link_out
                                          Associated OMIM IDs
                                          DrugBank ID DB00150 Link_out
                                          DrugBank Metabolite ID Not Available
                                          Phenol Explorer Compound ID Not Available
                                          Phenol Explorer Metabolite ID Not Available
                                          FoodDB ID FDB002250
                                          KNApSAcK ID C00001396 Link_out
                                          Chemspider ID 6066 Link_out
                                          KEGG Compound ID C00078 Link_out
                                          BioCyc ID TRP Link_out
                                          BiGG ID 33772 Link_out
                                          Wikipedia Link Kalma Link_out
                                          NuGOwiki Link HMDB00929 Link_out
                                          Metagene Link HMDB00929 Link_out
                                          METLIN ID 5879 Link_out
                                          PubChem Compound 6305 Link_out
                                          PDB ID TRP Link_out
                                          ChEBI ID 16828 Link_out
                                          References
                                          Synthesis Reference Amir-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. 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 Link_out
                                          2. 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 Link_out
                                          3. 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 Link_out
                                          4. 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 Link_out
                                          5. 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 Link_out
                                          6. 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 Link_out
                                          7. 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 Link_out
                                          8. 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 Link_out
                                          9. 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 Link_out
                                          10. 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 Link_out
                                          11. 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 Link_out
                                          12. 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 Link_out
                                          13. 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 Link_out
                                          14. 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 Link_out
                                          15. 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 Link_out
                                          16. 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 Link_out
                                          17. 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 Link_out
                                          18. 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 Link_out

                                          Enzymes
                                          Name: Aromatic-L-amino-acid decarboxylase
                                          Reactions:
                                          L-Tryptophan unknown Tryptamine + Carbon dioxide details
                                          Gene Name: DDC
                                          Uniprot ID: P20711 Link_out
                                          Protein Sequence: FASTA
                                          Gene Sequence: FASTA
                                          Name: Indoleamine 2,3-dioxygenase 1
                                          Reactions:
                                          L-Tryptophan + Oxygen unknown L-Formylkynurenine details
                                          Gene Name: IDO1
                                          Uniprot ID: P14902 Link_out
                                          Protein Sequence: FASTA
                                          Gene Sequence: FASTA
                                          Name: Tryptophan 5-hydroxylase 1
                                          Reactions:
                                          L-Tryptophan + L-erythro-tetrahydrobiopterin + Oxygen unknown Oxitriptan + 4a-Hydroxytetrahydrobiopterin details
                                          L-erythro-tetrahydrobiopterin + L-Tryptophan + Oxygen unknown Oxitriptan + 4a-Carbinolamine tetrahydrobiopterin + Water details
                                          Gene Name: TPH1
                                          Uniprot ID: P17752 Link_out
                                          Protein Sequence: FASTA
                                          Gene Sequence: FASTA
                                          Name: Tryptophan 5-hydroxylase 2
                                          Reactions:
                                          L-Tryptophan + L-erythro-tetrahydrobiopterin + Oxygen unknown Oxitriptan + 4a-Hydroxytetrahydrobiopterin details
                                          L-erythro-tetrahydrobiopterin + L-Tryptophan + Oxygen unknown Oxitriptan + 4a-Carbinolamine tetrahydrobiopterin + Water details
                                          Gene Name: TPH2
                                          Uniprot ID: Q8IWU9 Link_out
                                          Protein Sequence: FASTA
                                          Gene Sequence: FASTA
                                          Name: Tryptophan--tRNA ligase, cytoplasmic
                                          Reactions:
                                          Adenosine triphosphate + L-Tryptophan + tRNA(Trp) unknown Adenosine monophosphate + Pyrophosphate + L-tryptophyl-tRNA(Trp) details
                                          Adenosine triphosphate + L-Tryptophan + tRNA(Trp) unknown Adenosine monophosphate + Pyrophosphate + L-Tryptophanyl-tRNA(Trp) details
                                          Gene Name: WARS
                                          Uniprot ID: P23381 Link_out
                                          Protein Sequence: FASTA
                                          Gene Sequence: FASTA
                                          Name: Tryptophan--tRNA ligase, mitochondrial
                                          Reactions:
                                          Adenosine triphosphate + L-Tryptophan + tRNA(Trp) unknown Adenosine monophosphate + Pyrophosphate + L-tryptophyl-tRNA(Trp) details
                                          Adenosine triphosphate + L-Tryptophan + tRNA(Trp) unknown Adenosine monophosphate + Pyrophosphate + L-Tryptophanyl-tRNA(Trp) details
                                          Gene Name: WARS2
                                          Uniprot ID: Q9UGM6 Link_out
                                          Protein Sequence: FASTA
                                          Gene Sequence: FASTA
                                          Name: Tryptophan 2,3-dioxygenase
                                          Reactions:
                                          L-Tryptophan + Oxygen unknown L-Formylkynurenine details
                                          Gene Name: TDO2
                                          Uniprot ID: P48775 Link_out
                                          Protein Sequence: FASTA
                                          Gene Sequence: FASTA
                                          Name: Indoleamine 2,3-dioxygenase 2
                                          Reactions:
                                          L-Tryptophan + Oxygen unknown L-Formylkynurenine details
                                          Gene Name: IDO2
                                          Uniprot ID: Q6ZQW0 Link_out
                                          Protein Sequence: FASTA
                                          Gene Sequence: FASTA
                                          Name: L-amino-acid oxidase
                                          Reactions:
                                          L-Tryptophan + Water + Oxygen unknown Indolepyruvate + Ammonia + Hydrogen peroxide details
                                          Gene Name: IL4I1
                                          Uniprot ID: Q96RQ9 Link_out
                                          Protein Sequence: FASTA
                                          Gene Sequence: FASTA
                                          Transporters
                                          Name: Monocarboxylate transporter 8
                                          Reactions: Not Available
                                          Gene Name: SLC16A2
                                          Uniprot ID: P36021 Link_out
                                          Protein Sequence: FASTA
                                          Gene Sequence: FASTA
                                          Name: Monocarboxylate transporter 10
                                          Reactions: Not Available
                                          Gene Name: SLC16A10
                                          Uniprot ID: Q8TF71 Link_out
                                          Protein Sequence: FASTA
                                          Gene Sequence: FASTA