L-Tryptophan (T3D4369)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (7)XML
Targets (7)
Record Information
Version2.0
Creation Date2014-08-29 06:35:45 UTC
Update Date2018-03-21 17:46:25 UTC
Accession NumberT3D4369
Identification
Common NameL-Tryptophan
ClassSmall Molecule
DescriptionTryptophan is an essential amino acid that is the precursor of both serotonin and melatonin. Melatonin is a hormone that is produced by the pineal gland in animals, which regulates sleep and wakefulness. Serotonin is a brain neurotransmitter, platelet clotting factor, and neurohormone found in organs throughout the body. Metabolism of tryptophan into serotonin requires nutrients such as vitamin B6, niacin, and glutathione. Niacin (also known as vitamin B3) is an important metabolite of tryptophan. It is synthesized via kynurenine and quinolinic acids, which are products of tryptophan degradation. There are a number of 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. 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. 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. The requirement for tryptophan and protein decreases with age. The minimum daily requirement 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. A cup of low fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg of tryptophan per pound (http://www.dcnutrition.com). 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 by the pineal gland, which promotes sleep. 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 glutaric acidemia type 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: 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: 10721094). This pathological damage is further augmented by metabolites of the kynurenine pathway (a tryptophan degradation pathway).
Compound Type
  • Amine
  • Amino Acid, Essential
  • Animal Toxin
  • Antidepressive Agent, Second-Generation
  • Dietary Supplement
  • Drug
  • Food Toxin
  • Metabolite
  • Micronutrient
  • Natural Compound
  • Nutraceutical
  • Organic Compound
  • Supplement
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(-)-tryptophan
(2S)-2-amino-3-(1H-indol-3-yl)propanoate
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
(L)-tryptophan
(S)-1H-Indole-3-alanine
(S)-2-Amino-3-(3-indolyl)propionic acid
(S)-a-Amino-1H-indole-3-propanoate
(S)-a-Amino-1H-indole-3-propanoic acid
(S)-a-amino-b-indolepropionate
(S)-a-amino-b-indolepropionic acid
(S)-a-Aminoindole-3-propionate
(S)-a-Aminoindole-3-propionic acid
(S)-alpha-Amino-1H-indole-3-propanoate
(S)-alpha-Amino-1H-indole-3-propanoic acid
(S)-alpha-Amino-beta-(3-indolyl)-propionic acid
(S)-alpha-amino-beta-indolepropionate
(S)-alpha-amino-beta-indolepropionic acid
(S)-alpha-Aminoindole-3-propionate
(S)-alpha-Aminoindole-3-propionic acid
(S)-tryptophan
(S)-α-amino-1H-indole-3-propanoic acid
1-beta-3-Indolylalanine
1beta-3-Indolylalanine
1H-Indole-3-Alanine
2-Amino-3-indolylpropanoate
2-Amino-3-indolylpropanoic acid
3-(1H-Indol-3-yl)-L-Alanine
3-Indol-3-ylalanine
alpha'-Amino-3-indolepropionic acid
alpha-Aminoindole-3-propionic acid
Alti-Tryptophan
Ardeytropin
H-TRP-oh
Indole-3-alanine
Kalma
L-(-)-Tryptophan
L-(−)-tryptophan
L-alpha-Amino-3-indolepropionic acid
L-alpha-Aminoindole-3-propionic acid
L-b-3-Indolylalanine
L-beta-3-Indolylalanine
L-Tryptofan
L-Tryptophane
L-β-3-indolylalanine
Lopac-T-0254
Lyphan
Optimax
Pacitron
Sedanoct
Triptofano
Trofan
Trp
Tryptacin
Tryptan
Tryptophan
Tryptophane
Tryptophanum
W
Chemical FormulaC11H12N2O2
Average Molecular Mass204.225 g/mol
Monoisotopic Mass204.090 g/mol
CAS Registry Number73-22-3
IUPAC Name(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional NameL-tryptophan
SMILES[H][C@](N)(CC1=CNC2=CC=CC=C12)C(O)=O
InChI IdentifierInChI=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 KeyInChIKey=QIVBCDIJIAJPQS-VIFPVBQESA-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
  • L-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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Fibroblasts
  • Nerve Cells
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Transcription/TranslationSMP00019 Not Available
Tryptophan MetabolismSMP00063 map00380
Hartnup DisorderSMP00189 Not Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point290.5 dec°C
Boiling PointNot Available
Solubility1.34E+004 mg/L (at 25°C)
LogP-1.06
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 Area79.11 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.2 m³·mol⁻¹ChemAxon
Polarizability21.05 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-0190000000-feaec8547634dddcad8c2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-0390000000-45a6c4fd79081597d44a2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-0290000000-34f7274f31a4cb321a0b2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fk9-9270000000-9761607cbe821f87f1722014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-001i-0900000000-3faeed7ad32e1755c03c2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-0290000000-9c57a732e337fade3cb62014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-0900000000-d054a214c1717940989f2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0290000000-9860799c854e5c9ac1c72017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0190000000-feaec8547634dddcad8c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0390000000-45a6c4fd79081597d44a2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0290000000-34f7274f31a4cb321a0b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-0udi-3729000000-86129db57aaf1a245f932017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fk9-9270000000-9761607cbe821f87f1722017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0900000000-3faeed7ad32e1755c03c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-0290000000-9c57a732e337fade3cb62017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0560-4900000000-fa932bc4cffed0ca66b72016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9560000000-6829a8b2a2096883999f2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-06View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0910000000-db5439a5499b198817202012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014m-0900000000-cc4a579a29d19a1c0d442012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kf-3900000000-a931a9df4c855603d06e2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0290000000-5fa576241f151a3a01a22012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-417ea0b6e4e18e5fbde12012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-38f5ce97d594f3e3f12d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-783ffff22f31096f238f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0290000000-3ced9d310dda312f85822012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-a050919a36b995d345532012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-1ddec73daead0ffadce42012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-a8c9c60f075a675f66292012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0290602010-c09c931538bff74ac4002012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-0fed327c2a56f556e04c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0090000000-98ec1c2c012e58eab9242012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0090000000-fc77784da5d9b288d7512012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0290601010-d6f94902c0cf639cb7bc2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-27633a4f7ecfac45c7302012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0090000000-ee6cb8392b2e8d644bc12012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-d81c86eceee1c9824b022012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0190000000-0e8b883dc8ab06c89d772012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0uxu-2940000000-cb35b9680612e19d8b3a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-2900000000-7cc592351cc616b1d75f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-1900000000-987615a0add5eb2c31692012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-1900000000-f150d9d1e19c72d337a82012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4r-0690000000-ea2d79df0b56be85abdd2012-08-31View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityA number of important side reactions occur during the catabolism of tryptophan on the pathway to acetoacetate. The first enzyme of the catabolic pathway is an iron porphyrin oxygenase that opens the indole ring. The latter enzyme is highly inducible, its concentration rising almost 10-fold on a diet high in tryptophan. Kynurenine is the first key branch point intermediate in the pathway. Kynurenine undergoes deamniation in a standard transamination reaction yielding kynurenic acid. Kynurenic acid and metabolites have been shown to act as antiexcitotoxics and anticonvulsives. A second side branch reaction produces anthranilic acid plus alanine. Another equivalent of alanine is produced further along the main catabolic pathway, and it is the production of these alanine residues that allows tryptophan to be classified among the glucogenic and ketogenic amino acids. The second important branch point converts kynurenine into 2-amino-3-carboxymuconic semialdehyde, which has two fates. The main flow of carbon elements from this intermediate is to glutarate. An important side reaction in liver is a transamination and several rearrangements to produce limited amounts of nicotinic acid, which leads to production of a small amount of NAD+ and NADP+.
MetabolismHepatic.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesTryptophan may be useful in increasing serotonin production, promoting healthy sleep, managing depression by enhancing mental and emotional well-being, managing pain tolerance, and managing weight.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include agitation, confusion, diarrhea, fever, overactive reflexes, poor coordination, restlessness, shivering, sweating, talking or acting with excitement you cannot control, trembling or shaking, twitching, and vomiting.
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00150
HMDB IDHMDB00929
PubChem Compound ID6305
ChEMBL IDCHEMBL54976
ChemSpider ID6066
KEGG IDC00078
UniProt IDNot Available
OMIM ID
ChEBI ID16828
BioCyc IDTRP
CTD IDNot Available
Stitch IDNot Available
PDB IDTRP
ACToR IDNot Available
Wikipedia LinkKalma
References
Synthesis Reference

Sten Vilhelm Gatenbeck, Per Olof Hedman, “Fermentative process for the production of L-tryptophan and its derivatives.” U.S. Patent US3963572, issued April, 1974.

MSDSLink
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. [2472426 ]
  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. [15911239 ]
  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. [12297216 ]
  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. [14992292 ]
  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. [49200 ]
  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. [9849813 ]
  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. [2580417 ]
  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. [12137916 ]
  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. [2201566 ]
  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. [8884658 ]
  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. [2174666 ]
  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. [11811421 ]
  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. [408860 ]
  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. [1422788 ]
  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. [2669092 ]
  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. [15995595 ]
  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. [10493906 ]
  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. doi: 10.1038/nature07762. [19212411 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Tryptophan--tRNA ligase, cytoplasmic
General Function:
Tryptophan-trna ligase activity
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 Da
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. [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. [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. [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. [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. [16724112 ]
Target Details
2. Tryptophan--tRNA ligase, mitochondrial
General Function:
Tryptophan-trna ligase activity
Specific Function:
Not Available
Gene Name:
WARS2
Uniprot ID:
Q9UGM6
Molecular Weight:
40146.265 Da
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. [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. [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. [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. [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. [16636268 ]
Target Details
3. Alkaline phosphatase, tissue-nonspecific isozyme
General Function:
Pyrophosphatase activity
Specific Function:
This isozyme may play a role in skeletal mineralization.
Gene Name:
ALPL
Uniprot ID:
P05186
Molecular Weight:
57304.435 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC50>5 uMNot AvailableBindingDB 21974
References
  1. Lanier M, Sergienko E, Simao AM, Su Y, Chung T, Millan JL, Cashman JR: Design and synthesis of selective inhibitors of placental alkaline phosphatase. Bioorg Med Chem. 2010 Jan 15;18(2):573-9. doi: 10.1016/j.bmc.2009.12.012. Epub 2009 Dec 11. [20031422 ]
Target Details
4. Intestinal-type alkaline phosphatase
General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
ALPI
Uniprot ID:
P09923
Molecular Weight:
56811.695 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC50>5 uMNot AvailableBindingDB 21974
References
  1. Lanier M, Sergienko E, Simao AM, Su Y, Chung T, Millan JL, Cashman JR: Design and synthesis of selective inhibitors of placental alkaline phosphatase. Bioorg Med Chem. 2010 Jan 15;18(2):573-9. doi: 10.1016/j.bmc.2009.12.012. Epub 2009 Dec 11. [20031422 ]
Target Details
5. Phospholipase A-2-activating protein
General Function:
Phospholipase a2 activator activity
Specific Function:
Involved in the maintenance of ubiquitin levels.
Gene Name:
PLAA
Uniprot ID:
Q9Y263
Molecular Weight:
87156.21 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC50>5 uMNot AvailableBindingDB 21974
References
  1. Lanier M, Sergienko E, Simao AM, Su Y, Chung T, Millan JL, Cashman JR: Design and synthesis of selective inhibitors of placental alkaline phosphatase. Bioorg Med Chem. 2010 Jan 15;18(2):573-9. doi: 10.1016/j.bmc.2009.12.012. Epub 2009 Dec 11. [20031422 ]
Target Details
6. Stromelysin-1
General Function:
Zinc ion binding
Specific Function:
Can degrade fibronectin, laminin, gelatins of type I, III, IV, and V; collagens III, IV, X, and IX, and cartilage proteoglycans. Activates procollagenase.
Gene Name:
MMP3
Uniprot ID:
P08254
Molecular Weight:
53976.84 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC50>500 uMNot AvailableBindingDB 21974
References
  1. Ye QZ, Johnson LL, Nordan I, Hupe D, Hupe L: A recombinant human stromelysin catalytic domain identifying tryptophan derivatives as human stromelysin inhibitors. J Med Chem. 1994 Jan 7;37(1):206-9. [8289198 ]
Target Details
7. Tryptophan 2,3-dioxygenase
General Function:
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 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory11500 uMNot AvailableBindingDB 21974
References
  1. Dolusic E, Larrieu P, Moineaux L, Stroobant V, Pilotte L, Colau D, Pochet L, Van den Eynde B, Masereel B, Wouters J, Frederick R: Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators. J Med Chem. 2011 Aug 11;54(15):5320-34. doi: 10.1021/jm2006782. Epub 2011 Jul 18. [21726069 ]