Showing Compound Card for Tryptophan (CDB000061)

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Record Information
Version1.0
Created at2020-03-18 23:23:20 UTC
Updated at2022-12-13 23:36:25 UTC
CannabisDB IDCDB000061
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameTryptophan
DescriptionTryptophan, (±)-Tryptophan or L-tryptophan abbreviated Trp or W, an aromatic amino acid, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. It is an essential amino acid (meaning the body cannot synthesize it; it must be obtained from the diet) that is necessary for normal growth in infants and for nitrogen balance in adults. Tryptophan is a strong basic compound. It is a pale yellow to yellow crystalline powder. Tryptophan is found in highest concentrations in red bell peppers, caseins, and dried milks and in a lower concentrations in remoulades, clawed lobsters, and garden cress. (±)-Tryptophan has also been detected in snack foods, common lings, rapes, bamboo shoots, and other fish products making (±)-tryptophan a potential biomarker for the consumption of these foods. The minimum daily requirement for tryptophan for adults is 3 mg/kg/day or about 200 mg a day. There is 400 mg of tryptophan in a cup of wheat germ, 300 mg of tryptophan a cup of low-fat cottage cheese and up to 600 mg of tryptophan per pound in chicken and turkey ( Ref:DOI dcnutrition. com). It is an amino acid found in cannabis plants (PMID: Ref:DOI ncbi.nlm.nih.gov/pubmed/6991645">6991645 ). Plants and microorganisms commonly synthesize tryptophan from shikimic acid or anthranilate. In the latter pathway, phosphoribosylphospho transferase condenses anthranilate with phosphoribosylpyrophosphate (PRPP), generating pyrophosphate and phosphoribosyl anthranilate. Phosphoribosyl anthranilate isomerase isomerizes phosphoribosyl anthranilate into carboyxphenylamino-deoxyribulose 5-phosphate which is then subjected to reductive decarboxylation by indole glycerol synthase, producing indole-3-glycerol phosphate; this, in turn, is transformed into indole. In the last step, tryptophan synthase catalyzes the formation of tryptophan from indole and the amino acid serine (PMID: Ref:DOI ncbi.nlm.nih.gov/pubmed/7640526">7640526 ). Tryptophan is used as nutrient supplement and as an active ingredient in pharmaceutical products. It is a precursor of indole alkaloids and auxins (phytohormones; PMID: Ref:DOI ncbi.nlm.nih.gov/pubmed/18394986">18394986 ) in plants, In mammals, tryptophan is a precursor of serotonin (a neurotransmitter, a platelet clotting factor, and a neurohormone found in organs throughout the body; PMID: Ref:DOI ncbi.nlm.nih.gov/pubmed/26560523">26560523 ), melatonin (a neurohormone produced by the pineal gland in animals, which regulates sleep and wakefulness; PMID: Ref:DOI ncbi.nlm.nih.gov/pubmed/4391290">4391290 ) and niacin (also known as Vitamin B3, synthesized via kynurenine and quinolinic acids, which are products of tryptophan degradation; PMID: Ref:DOI ncbi.nlm.nih.gov/pubmed/14284754">14284754 ). Tryptophan plays a role in "feast-induced" drowsiness. Ingestion of a meal rich in carbohydrates triggers the release of insulin. Insulin, in turn, stimulates the uptake of large neutral branched-chain amino acids (BCAAs) into muscle, increasing the ratio of tryptophan to BCAA in the bloodstream. The increased tryptophan ratio reduces competition at the large neutral amino acid transporter (which transports both BCAAs and tryptophan), resulting in greater uptake of tryptophan across the blood-brain barrier into the cerebrospinal fluid (CSF). Once in the CSF, tryptophan is converted into serotonin and the resulting serotonin is further metabolized into melatonin which promotes sleepiness. There are a few conditions or diseases that are characterized tryptophan deficiencies. For instance, fructose malabsorption causes improper absorption of tryptophan in the intestine, which reduces levels of tryptophan in the blood and leads to depression. High corn or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea, and dementia (PMID: Ref:DOI ncbi.nlm.nih.gov/pubmed/16207585">16207585 ). Hartnup's disease is a disorder in which tryptophan and other amino acids are not absorbed properly. Symptoms of Hartnup's disease include skin rashes, difficulty coordinating movements (cerebellar ataxia), and psychiatric symptoms such as depression or psychosis. Tryptophan supplements may be useful for treating Hartnup's disease. 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 breakdown products (such as kynurenine) correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension, and anxiety states. Under certain situations, tryptophan can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that causes damage to the brain and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of tryptophan can be found in glutaric aciduria type I (glutaric acidemia type I or GA1). GA1 is an inherited disorder in which the body is unable to completely break down the amino acids lysine, hydroxylysine, and tryptophan. Babies with GA I are often born with unusually large heads (macrocephaly). Affected individuals may also have difficulty moving and may experience spasms, jerking, rigidity or decreased muscle tone, and muscle weakness. High levels of tryptophan have also been implicated in eosinophilia-myalgia syndrome (EMS), an incurable and sometimes fatal flu-like neurological condition linked to the ingestion of large amounts of L-tryptophan. The risk of developing EMS increases with larger doses of tryptophan and increasing age. Some research suggests that certain genetic polymorphisms may be related to the development of EMS. The presence of eosinophilia is a core feature of EMS, along with unusually severe myalgia (muscle pain). It is thought that both tryptophan and certain unidentified tryptophan contaminants may contribute to EMS (PMID: Ref:DOI ncbi.nlm.nih.gov/pubmed/1763543">1763543 ). It has also been suggested that excessive tryptophan or elevation of its metabolites could play a role in amplifying some of the pathological features of EMS (PMID: Ref:DOI ncbi.nlm.nih.gov/pubmed/10721094">10721094 ). This pathological damage is further augmented by metabolites of the kynurenine pathway (a tryptophan degradation pathway). 
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-2-Amino-3-(1H-indol-3-yl)propanoic acidChEBI
(R)-TryptophanChEBI
DTRChEBI
(2R)-2-Amino-3-(1H-indol-3-yl)propanoateGenerator
(+)-TryptophanHMDB
(R)-(+)-2-amino-3-(3-Indolyl)propionic acidHMDB
(R)-2-amino-3-(3-Indolyl)propionic acidHMDB
D-(+)-TryptophanHMDB
D-alpha-amino-3-Indolepropionic acidHMDB
D-TryptophaneHMDB
D-TrytophaneHMDB
delta-(+)-TryptophanHMDB
delta-alpha-amino-3-Indolepropionic acidHMDB
delta-TryptophaneHMDB
delta-TrytophaneHMDB
DL-TryptophanHMDB
H-D-TRP-OHHMDB
H-delta-TRP-OHHMDB
TryptophanHMDB
Chemical FormulaC11H12N2O2
Average Molecular Weight204.23
Monoisotopic Molecular Weight204.0899
IUPAC Name(2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional NameD-tryptophan
CAS Registry Number153-94-6
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-/m1/s1
InChI KeyQIVBCDIJIAJPQS-SECBINFHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • D-alpha-amino acid
  • 3-alkylindole
  • Indole
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point282 - 85 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.4 g/L at 25 °CWikipedia
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 Area79.11 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.2 m³·mol⁻¹ChemAxon
Polarizability21.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTryptophan, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0560-4900000000-fa932bc4cffed0ca66b7Spectrum
Predicted GC-MSTryptophan, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00gl-7490000000-c8150f8039963f4eb7f7Spectrum
Predicted GC-MSTryptophan, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , negativesplash10-0gi0-4940000000-00a5a8140b79080185e62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0gi0-3940000000-321dc703abd716322faa2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000j-0900000000-75b4d705a8e2930848e32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000j-0900000000-5ce443f4be2efcf027ea2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0uxr-1960000000-3944aa089c0be5dbd57a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014i-0900000000-94061fd1f6b08445cdf32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-014i-2900000000-38dfecc1b9b9268a08b02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0900000000-e2372bfee8fef603c90e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0930000000-da94834297fcc5b3d3c52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 25V, Negativesplash10-0zfr-0890000000-0d359faeb8858c021feb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-e78172f4f27df232466e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0790000000-b95264f9ab42781784572021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-e13b1ada6628c7f81fad2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-014i-0900000000-93406e2cdb79770abc7d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-c73c9b49139319c80b182021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 65V, Negativesplash10-0udi-0690000000-4bf908b56440e171f5452021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-0udi-0190000000-dfe53dc7eb1d8480b67d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0900000000-78f68b1fae52ebe105932021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 95V, Negativesplash10-014i-1910000000-d9efdaa0c5d83afa0a302021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0920000000-48b0cf647bfaeff827492016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-ae69c675905bf421649d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-0189d8e97d18427f2b042016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3290000000-670b28bfa8011e4915e02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9730000000-c2c5e2644b01d811fce02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9600000000-06c476c7e459db7aa6b42016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Indoleamine 2,3-dioxygenase 1IDO18p12-p11P14902 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Indoleamine 2,3-dioxygenase 1IDO18p12-p11P14902 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.396 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.846 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.399 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.244 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.210 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.166 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0013609
DrugBank IDDB03225
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029595
KNApSAcK IDC00052033
Chemspider ID8707
KEGG Compound IDC00525
BioCyc IDD-TRYPTOPHAN
BiGG IDNot Available
Wikipedia LinkTryptophan
METLIN IDNot Available
PubChem Compound9060
PDB IDNot Available
ChEBI ID16296
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Radwanski ER, Last RL: Tryptophan biosynthesis and metabolism: biochemical and molecular genetics. Plant Cell. 1995 Jul;7(7):921-34. doi: 10.1105/tpc.7.7.921. [PubMed:7640526 ]
  3. Palme K, Nagy F: A new gene for auxin synthesis. Cell. 2008 Apr 4;133(1):31-2. doi: 10.1016/j.cell.2008.03.014. [PubMed:18394986 ]
  4. Strasser B, Gostner JM, Fuchs D: Mood, food, and cognition: role of tryptophan and serotonin. Curr Opin Clin Nutr Metab Care. 2016 Jan;19(1):55-61. doi: 10.1097/MCO.0000000000000237. [PubMed:26560523 ]
  5. Wurtman RJ, Anton-Tay F: The mammalian pineal as a neuroendocrine transducer. Recent Prog Horm Res. 1969;25:493-522. doi: 10.1016/b978-0-12-571125-8.50014-4. [PubMed:4391290 ]
  6. IKEDA M, TSUJI H, NAKAMURA S, ICHIYAMA A, NISHIZUKA Y, HAYAISHI O: STUDIES ON THE BIOSYNTHESIS OF NICOTINAMIDE ADENINE DINUCLEOTIDE. II. A ROLE OF PICOLINIC CARBOXYLASE IN THE BIOSYNTHESIS OF NICOTINAMIDE ADENINE DINUCLEOTIDE FROM TRYPTOPHAN IN MAMMALS. J Biol Chem. 1965 Mar;240:1395-401. [PubMed:14284754 ]
  7. Pitche PT: [Pellagra]. Sante. 2005 Jul-Sep;15(3):205-8. [PubMed:16207585 ]
  8. Milburn DS, Myers CW: Tryptophan toxicity: a pharmacoepidemiologic review of eosinophilia-myalgia syndrome. DICP. 1991 Nov;25(11):1259-62. doi: 10.1177/106002809102501116. [PubMed:1763543 ]
  9. Gross B, Ronen N, Honigman S, Livne E: Tryptophan toxicity--time and dose response in rats. Adv Exp Med Biol. 1999;467:507-16. [PubMed:10721094 ]

Enzymes

Enzyme Details
1. Indoleamine 2,3-dioxygenase 1
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