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Human Metabolome Database Version 3.5

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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 | 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
  • Food
  • Drug
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 Comments
Blood Detected and Quantified
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54.5 +/- 9.7 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
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78.4 +/- 15.5 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
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44.0 (37.0-51.0) uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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48.7 +/- 11.6 uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
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101.5 +/- 27.2 uM Newborn (0-30 days old) Both Normal Not Available
Blood Detected and Quantified
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45.0 +/- 9.0 uM Adult (>18 years old) Male Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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5 +/- 3 uM Not Specified Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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1.3 +/- 0.4 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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2.32 +/- 0.09 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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2.25 +/- 0.95 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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20.4 +/- 8.2 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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2.0 +/- 0.53 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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2.0 (1.2-2.5) uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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15.9 +/- 4.1 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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2.64 +/- 0.52 uM Adult (>18 years old) Both Normal Not Available
Saliva Detected and Quantified
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0.5 +/- 0.5 uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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7.8 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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2.45-29.40 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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13.52 +/- 7.37 umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
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4.62 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
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5.6 (9.3-2.1) umol/mmol creatinine Adult (>18 years old) Both Normal by LC-MS/MS (Biocrates kit)
Urine Detected and Quantified
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6.3 (3.4-11.1) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
Article_icon
3.9 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
5.263 (1.316-9.211) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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83.3 +/- 26.0 uM Adult (>18 years old) Male Schizophrenia Not Available
Blood Detected and Quantified
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80.2 +/- 22.0 uM Adult (>18 years old) Female Schizophrenia Not Available
Blood Detected and Quantified
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31.6 (29.6-33.6) uM Adult (>18 years old) Both Epilepsy Acute seizures
Blood Detected and Quantified
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37.2 (34.3-40.1) uM Adult (>18 years old) Both Epilepsy Juvenile myoclonic epilepsy (JME)
Blood Detected and Quantified
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53.3 (50.3-56.3) uM Adult (>18 years old) Both Epilepsy Refractory localization-related epilepsy (RLE)
Blood Detected and Quantified
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33.06 +/- 8.99 uM Adult (>18 years old) Both Alzheimer's disease Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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2.035 +/- 0.649 uM Adult (>18 years old) Not Specified celiac disease Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.0018 +/- 0.0003 uM Adult (>18 years old) Both Hypothyroidism Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
1.6 +/- 0.3 uM Adult (>18 years old) Both Hypothyroidism Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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1.0 +/- 0.2 uM Children (1-13 year old) Both Hartnup Disease Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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1.7 +/- 0.27 uM Adult (>18 years old) Both Epilepsy Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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1.6+/- 0.57 uM Adult (>18 years old) Both Epilepsy Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
1.7 +/- 0.4 uM Adult (>18 years old) Not Specified Epilepsy Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
1.68 +/- 0.52 uM Adult (>18 years old) Both Epilepsy Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
14.3 +/- 12.5 uM Adult (>18 years old) Not Specified Epilepsy Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
11.5 +/- 8.2 uM Adult (>18 years old) Not Specified Epilepsy Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
13.0 +/- 5.2 uM Children (1-13 year old) Not Specified Leukemia Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
12.8 +/- 3.5 uM Children (1-13 year old) Not Specified Leukemia Acute Lymphoblastic Leukemia (ALL) with Central...
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
2.42 +/- 0.14 uM Adult (>18 years old) Not Specified Olivopontocerebellar atrophy (OPCA) Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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1.80 +/- 0.2 uM Adult (>18 years old) Not Specified Spastic Ataxia Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
1.8 +/- 0.3 uM Adult (>18 years old) Not Specified Hypothyroidism Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
1.3 +/- 0.32 uM Adult (>18 years old) Both Alzheimer's disease Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
2.4 +/- 0.13 uM Not Specified Not Specified Friedreich's ataxia Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
2.67 +/- 0.6 uM Adult (>18 years old) Both Schizophrenia Not Available
Urine Detected and Quantified
Article_icon
7.83 +/- 7.48 umol/mmol creatinine Adult (>18 years old) Both Cachexia Not Available
Urine Detected and Quantified
Article_icon
1.19 +/- 0.23 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease Not Available
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
                      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:
                      • (1) 3,4-dihydroxy-L-phenylalanine = dopamine + CO2 [RN:R02080]
                      • (2) 5-hydroxy-L-tryptophan = 5-hydroxytryptamine + CO2 [RN:R02701]
                      Gene Name: DDC
                      Uniprot ID: P20711 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Indoleamine 2,3-dioxygenase 1
                      Reactions:
                      • (1) D-tryptophan + O2 = N-formyl-D-kynurenine [RN:R07362]
                      • (2) L-tryptophan + O2 = N-formyl-L-kynurenine [RN:R00678]
                      Gene Name: IDO1
                      Uniprot ID: P14902 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Tryptophan 5-hydroxylase 1
                      Reactions:
                      • L-tryptophan + tetrahydrobiopterin + O2 = 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin [RN:R07213]
                      Gene Name: TPH1
                      Uniprot ID: P17752 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Tryptophan 5-hydroxylase 2
                      Reactions:
                      • L-tryptophan + tetrahydrobiopterin + O2 = 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin [RN:R07213]
                      Gene Name: TPH2
                      Uniprot ID: Q8IWU9 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Tryptophanyl-tRNA synthetase, cytoplasmic
                      Reactions:
                      • ATP + L-tryptophan + tRNATrp = AMP + diphosphate + L-tryptophyl-tRNATrp [RN:R03664]
                      Gene Name: WARS
                      Uniprot ID: P23381 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Tryptophanyl-tRNA synthetase, mitochondrial
                      Reactions:
                      • ATP + L-tryptophan + tRNATrp = AMP + diphosphate + L-tryptophyl-tRNATrp [RN:R03664]
                      Gene Name: WARS2
                      Uniprot ID: Q9UGM6 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Tryptophan 2,3-dioxygenase
                      Reactions:
                      • L-tryptophan + O2 = N-formyl-L-kynurenine [RN:R00678]
                      Gene Name: TDO2
                      Uniprot ID: P48775 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Indoleamine 2,3-dioxygenase 2
                      Reactions:
                        Gene Name: IDO2
                        Uniprot ID: Q6ZQW0 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Transporters
                        Name: Monocarboxylate transporter 8
                        Reactions:
                        • --- []
                        Gene Name: SLC16A2
                        Uniprot ID: P36021 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Monocarboxylate transporter 10
                        Reactions:
                          Gene Name: SLC16A10
                          Uniprot ID: Q8TF71 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA