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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-17 18:51:35 UTC
NP-MRD IDNP0001161
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Tryptophan
DescriptionTryptophan (Trp) or L-tryptophan is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-tryptophan is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Tryptophan is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aromatic amino acid. Tryptophan is an essential amino acid, meaning the body cannot synthesize it, and it must be obtained from the diet. 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 is particularly plentiful in chocolate, oats, dried dates, milk, yogurt, cottage cheese, red meat, eggs, fish, poultry, sesame, chickpeas, almonds, sunflower seeds, pumpkin seeds, buckwheat, spirulina, and peanuts. Tryptophan 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 by 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 diets 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 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. 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. Because tryptophan is converted into 5-hydroxytryptophan (5-HTP) which is then converted into the neurotransmitter serotonin, it has been proposed that consumption of tryptophan or 5-HTP may improve depression symptoms by increasing the level of serotonin in the brain. Tryptophan is sold over the counter in the United States (after being banned to varying extents between 1989 and 2005) and the United Kingdom as a dietary supplement for use as an antidepressant, anxiolytic, and sleep aid. It is also marketed as a prescription drug in some European countries for the treatment of major depression. There is evidence that blood tryptophan levels are unlikely to be altered by changing the diet, but consuming purified tryptophan increases the serotonin level in the brain, whereas eating foods containing tryptophan does not. This is because the transport system that brings tryptophan across the blood–brain barrier also transports other amino acids which are contained in protein food sources. 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 due to a deficiency of mitochondrial glutaryl-CoA dehydrogenase (EC 1.3.99.7, GCDH). Excessive levels of their intermediate breakdown products (e.G. Glutaric acid, glutaryl-CoA, 3-hydroxyglutaric acid, glutaconic acid) can accumulate and cause damage to the brain (and also other organs), but particularly the basal ganglia. Babies with glutaric acidemia type I are often born with unusually large heads (macrocephaly). Other symptoms include spasticity (increased muscle tone/stiffness) and dystonia (involuntary muscle contractions resulting in abnormal movement or posture), but many affected individuals are asymptomatic. 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).
Structure
Thumb
Synonyms
ValueSource
(2S)-2-Amino-3-(1H-indol-3-yl)propanoic acidChEBI
(S)-alpha-Amino-1H-indole-3-propanoic acidChEBI
(S)-alpha-Amino-beta-(3-indolyl)-propionic acidChEBI
(S)-TryptophanChEBI
L-(-)-TryptophanChEBI
L-beta-3-IndolylalanineChEBI
TrpChEBI
TryptophanChEBI
WChEBI
(2S)-2-Amino-3-(1H-indol-3-yl)propanoateGenerator
(S)-a-Amino-1H-indole-3-propanoateGenerator
(S)-a-Amino-1H-indole-3-propanoic acidGenerator
(S)-alpha-Amino-1H-indole-3-propanoateGenerator
(S)-Α-amino-1H-indole-3-propanoateGenerator
(S)-Α-amino-1H-indole-3-propanoic acidGenerator
(S)-a-Amino-b-(3-indolyl)-propionateGenerator
(S)-a-Amino-b-(3-indolyl)-propionic acidGenerator
(S)-alpha-Amino-beta-(3-indolyl)-propionateGenerator
(S)-Α-amino-β-(3-indolyl)-propionateGenerator
(S)-Α-amino-β-(3-indolyl)-propionic acidGenerator
L-b-3-IndolylalanineGenerator
L-Β-3-indolylalanineGenerator
(-)-TryptophanHMDB
(L)-TryptophanHMDB
(S)-1H-Indole-3-alanineHMDB
(S)-2-Amino-3-(3-indolyl)propionic acidHMDB
(S)-a-Amino-b-indolepropionateHMDB
(S)-a-Amino-b-indolepropionic acidHMDB
(S)-a-Aminoindole-3-propionateHMDB
(S)-a-Aminoindole-3-propionic acidHMDB
(S)-alpha-Amino-beta-indolepropionateHMDB
(S)-alpha-Amino-beta-indolepropionic acidHMDB
(S)-alpha-Aminoindole-3-propionateHMDB
(S)-alpha-Aminoindole-3-propionic acidHMDB
1-beta-3-IndolylalanineHMDB
1beta-3-IndolylalanineHMDB
1H-Indole-3-alanineHMDB
2-Amino-3-indolylpropanoateHMDB
2-Amino-3-indolylpropanoic acidHMDB
3-(1H-indol-3-yl)-L-AlanineHMDB
3-indol-3-YlalanineHMDB
Alpha'-amino-3-indolepropionic acidHMDB
alpha-Aminoindole-3-propionic acidHMDB
ArdeytropinHMDB
H-TRP-OHHMDB
Indole-3-alanineHMDB
KalmaHMDB
L-alpha-Amino-3-indolepropionic acidHMDB
L-alpha-Aminoindole-3-propionic acidHMDB
L-TryptofanHMDB
L-TryptophaneHMDB
Lopac-T-0254HMDB
LyphanHMDB
OptimaxHMDB
PacitronHMDB
SedanoctHMDB
TriptofanoHMDB
TrofanHMDB
TryptacinHMDB
TryptanHMDB
TryptophaneHMDB
TryptophanumHMDB
ArdeydormHMDB
L TryptophanHMDB
L-Tryptophan-ratiopharmHMDB
Merck brand OF tryptophanHMDB
Niddapharm brand OF tryptophanHMDB
ICN brand OF tryptophanHMDB
LevotryptophanHMDB
PMS TryptophanHMDB
PMS-TryptophanHMDB
Ratiopharm brand OF tryptophanHMDB
Esparma brand OF tryptophanHMDB
Ratio-tryptophanHMDB
L Tryptophan ratiopharmHMDB
NaturruheHMDB
Tryptophan metabolism alterationsHMDB
Ardeypharm brand OF tryptophanHMDB
Kalma brand OF tryptophanHMDB
Pharmascience brand OF tryptophanHMDB
Upsher-smith brand OF tryptophanHMDB
Ratio tryptophanHMDB
Chemical FormulaC11H12N2O2
Average Mass204.2252 Da
Monoisotopic Mass204.08988 Da
IUPAC Name(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional NameL-tryptophan
CAS Registry Number73-22-3
SMILES
N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O
InChI Identifier
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
InChI KeyQIVBCDIJIAJPQS-VIFPVBQESA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-08-07View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-17View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-02-17View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abramis bramaFooDB
AcipenserFooDB
AcipenseridaeFooDB
Actinidia chinensisFooDB
Agaricus bisporus
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium chinenseLOTUS Database
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Alosa sapidissimaFooDB
Aloysia triphylla
AmaranthusFooDB
Amaranthus spinosusLOTUS Database
Amelanchier alnifolia
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskei
AnguillaFooDB
AnguilliformesFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anoplopoma fimbriaFooDB
Anthriscus cerefolium
Antirrhinum majusKNApSAcK Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceum
Apium graveolens var. secalinum
Aplodinotus grunniensFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Archosargus probatocephalusFooDB
Arctium lappaFooDB
Armoracia rusticana
Artemia salinaLOTUS Database
Artemisia absinthiumLOTUS Database
Artemisia armeniacaLOTUS Database
Artemisia dracunculus
Artemisia vulgaris
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Ascaris lumbricoidesLOTUS Database
Asparagus officinalisFooDB
Aspergillus clavatusFungi
Aspergillus fischeriFungi
Aspergillus fumigatusFungi
AstacideaFooDB
Atractylodes lanceaLOTUS Database
Attalea speciosa
Auricularia auricula-judae
Auricularia polytricha
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
BivalviaFooDB
Bombyx moriLOTUS Database
Borago officinalis
Bos taurusFooDB
BrachyuraFooDB
Brassica alboglabra
Brassica juncea
Brassica napus
Brassica napus ssp. rapiferaPlant
Brassica napus var. napus
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridis
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensis
Brassica rapa var. rapaFooDB
Brassica ruvo
Brosimum alicastrumFooDB
Brosme brosmeFooDB
Bubalus bubalisFooDB
BuccinidaeFooDB
Bupleurum chinenseLOTUS Database
Byrsonima crassifolia
Cajanus cajanFooDB
Callinectes sapidusFooDB
Canarium ovatumFooDB
Cancer magisterFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibarius
Capparis spinosa
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.
Capsicum annuum var. annuumFooDB
Capsicum chinense
Capsicum pubescens
Carica papaya L.FooDB
CarideaFooDB
Carissa macrocarpa
Carthamus tinctorius
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Catostomus commersoniiFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobile
Chamerion angustifolium
Chanos chanosFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chionoecetes opilioFooDB
Chrysanthemum coronarium
Cicer arietinumFooDB
CichlidaeFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticum
Cinnamomum verum
Cirsium
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limon
Citrus maxima
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cliona celataLOTUS Database
Clupea harengus harengusFooDB
Clupea pallasiiFooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
CoregonusFooDB
Coregonus artediFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crassostrea gigasFooDB
Crassostrea virginicaFooDB
Crateva religiosa
Crocus sativus
Ctenodiscus crispatusLOTUS Database
Cucumis melo
Cucumis metuliferus
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminum
Curcuma domesticaKNApSAcK Database
Curcuma longaFooDB
Cydonia oblonga
Cymbopogon citratus
Cynara cardunculus
Cynara scolymus
Cynomorium songaricumLOTUS Database
Cyprinus carpioFooDB
Daphnia pulexLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Davallia mariesiiLOTUS Database
Dimocarpus longan
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinus
Dysphania ambrosioides
ElaeisFooDB
Eleocharis dulcis
Elettaria cardamomum
Empetrum nigrum
EngraulidaeFooDB
Engraulis encrasicolusFooDB
EpinephelusFooDB
Equisetum debileKNApSAcK Database
Equisetum ramosissimumLOTUS Database
Equisetum ramosissimum subsp. debilePlant
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. Sativa
Ervatamia coronariaLOTUS Database
Esox luciusFooDB
Eugenia javanica
Eugenia uniflora
Eutrema japonicum
Fagopyrum esculentumFooDB
Fagopyrum tataricum
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipes
Foeniculum vulgareFooDB
Fragaria chiloensisLOTUS Database
Fragaria x ananassa
GadiformesFooDB
GadusFooDB
Gadus macrocephalusFooDB
Gadus morhuaFooDB
Garcinia mangostana
Gaylussacia baccata
Geranium pratenseLOTUS Database
Geranium pratense subsp.finitimum (Woronow) KnuthKNApSAcK Database
Ginkgo bilobaFooDB
Glehnia littoralisLOTUS Database
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinum
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffa
HippoglossusFooDB
Hippoglossus hippoglossusFooDB
Hippoglossus stenolepisFooDB
Hippophae rhamnoides
Homarus americanusFooDB
Homo sapiensLOTUS Database
Hoplostethus atlanticusFooDB
Hordeum vulgareFooDB
Hypholoma fasciculareLOTUS Database
Hyssopus officinalis L.
Ictalurus punctatusFooDB
Illicium verum
Ipomoea aquatica
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifolia
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Katsuwonus pelamisFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
LaminariaFooDB
Lathyrus sativus
Laurus nobilis L.
Leiostomus xanthurusFooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativum
Lepomis gibbosusFooDB
LeporidaeFooDB
Leptasterias polarisLOTUS Database
Lethasterias nanimensisLOTUS Database
Levisticum officinale
Linum usitatissimumFooDB
Litchi chinensis
Lophius piscatoriusFooDB
Lopholatilus chamaeleonticepsFooDB
Lota lotaFooDB
Luffa aegyptiaca
Luffariella geometrica-
LupinusFooDB
Lupinus albusFooDB
LutjanidaeFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginata
Malus
Malus pumilaFooDB
Mammea americana
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Marchantia polymorphaLOTUS Database
Matricaria recutita
Matteuccia struthiopteris
Medicago sativa
Meleagris gallopavoFooDB
Melissa officinalis L.
Mentha
Mentha aquatica
Mentha arvensis
Mentha spicataFooDB
Mentha x piperitaFooDB
Merlangius merlangusFooDB
Mespilus germanica
Metroxylon sagu
Micropogonias undulatusFooDB
Microstomus kittFooDB
Mimosa pudicaLOTUS Database
Mirabilis jalpaKNApSAcK Database
Molva molvaFooDB
Momordica charantia
Morchellaceae
Morella rubra
Moringa oleiferaFooDB
Morone saxatilisFooDB
Morus
Morus nigra
Mugil cephalusFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
Mycoplasmopsis bovisLOTUS Database
Myrica
Myristica fragrans
MytilidaeFooDB
Mytilus edulisFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceum
NephropidaeFooDB
Neptunea antiquaLOTUS Database
Numida meleagrisFooDB
Nuphar lutea
Ocimum basilicumFooDB
Octopus vulgarisFooDB
Oenothera biennisFooDB
Olea europaea
Oncorhynchus gorbuschaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
Onobrychis viciifoliaLOTUS Database
Ophiodon elongatusFooDB
Opuntia
Opuntia cochenilliferaFooDB
Opuntia ficus-indicaLOTUS Database
Opuntia macrorhiza
Origanum majorana
Origanum onites
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
OsmeridaeFooDB
Osmerus mordaxFooDB
Pachyrhizus erosus
PalinuridaeFooDB
Panax ginseng
Panax notoginsengLOTUS Database
Pangium edule
Panicum miliaceumFooDB
Paralithodes camtschaticusFooDB
Passiflora edulis
Pastinaca sativa
PectinidaeFooDB
Pediomelum esculentumFooDB
Penicillium aethiopicumFungi
Pennisetum americanumLOTUS Database
Peprilus triacanthusFooDB
PercoideiFooDB
Perideridia oregana
Periplaneta americanaLOTUS Database
Persea americanaFooDB
Petasites japonicus
Petroselinum crispumFooDB
Peucedanum japonicumLOTUS Database
Phaseolus coccineus
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpa
Phyllostachys edulisFooDB
Physalis
Physalis philadelphica var. immaculata
Phytolacca americana
Pimenta dioica
Pimpinella anisum
PinusFooDB
Pinus edulisFooDB
Pinus ponderosaLOTUS Database
Piper kadsuraLOTUS Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
PleuronectiformesFooDB
Pleurotus ostreatusFooDB
Plumbago zeylanicaKNApSAcK Database
PollachiusFooDB
Pollachius pollachiusFooDB
Polygonum alpinum
Pomatomus saltatrixFooDB
Populus tremulaLOTUS Database
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Pratia nummulariaKNApSAcK Database
Prosopis julifloraLOTUS Database
Prosopis juliflora (Sw.) DC.KNApSAcK Database
Prunus armeniacaFooDB
Prunus avium
Prunus avium L.
Prunus cerasus
Prunus domestica
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosa
Prunus virginiana
Pseudo-nitzschia multistriataLOTUS Database
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatum
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativus
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarum
Ribes aureum
Ribes glandulosum
Ribes nigrum
Ribes rubrum
Ribes uva-crispaFooDB
Ripariosida hermaphroditaLOTUS Database
Rosa
Rubus arcticus
Rubus chamaemorus
Rubus idaeus
Rubus occidentalis
Rubus spectabilis
Rumex
Rumex acetosa
Rumex articus
Sagittaria latifolia
Sagittaria sagittifoliaLOTUS Database
Salix pulchra
Salmo salarFooDB
Salmo trutta forma truttaFooDB
SalmonidaeFooDB
Salvia elegans
Salvia hispanicaFooDB
Salvia officinalis
Salvia rosmarinusFooDB
Sambucus nigra
Sambucus nigra L.
Satureja hortensis L.
Satureja montana
Scomberomorus cavallaFooDB
Scomberomorus maculatusFooDB
Scophthalmus maximusFooDB
Scorzonera hispanica
Scrophularia cryptophilaLOTUS Database
SebastesFooDB
Sebastes alutusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
SepiidaeFooDB
Seriola lalandiFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
SiluriformesFooDB
Sinapis albaFooDB
Sisymbrium
Smallanthus sonchifoliusLOTUS Database
Solanum lycopersicum
Solanum lycopersicum var. cerasiforme
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoense
Solanum tuberosumFooDB
SoleidaeFooDB
Sorbus aucuparia
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
SpirulinaFooDB
SqualiformesFooDB
Stenodus leucichthysFooDB
Stenotomus chrysopsFooDB
Stratiotes aloidesLOTUS Database
Streptomyces albidoflavusLOTUS Database
Streptomyces venezuelaeLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cumini
Syzygium jambos
Tamarindus indicaFooDB
Taraxacum officinale
Tecoma stansLOTUS Database
Telekia speciosaLOTUS Database
Tetragonia tetragonioides
TeuthidaFooDB
Thalassiosira pseudonanaLOTUS Database
Thelesperma
Thunnus albacaresFooDB
Thunnus thynnusFooDB
Thymus pulegioides
Thymus vulgarisFooDB
Tilia cordata
Tilia L.
Trachinotus carolinusFooDB
Trachurus symmetricusFooDB
Tragopogon porrifolius
Treculia africanaLOTUS Database
Trifolium pratense L.KNApSAcK Database
Trifolium repensPlant
Trifolium repens L.KNApSAcK Database
Trigonella foenum-graecumFooDB
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Typha angustifolia
Ulmus thomasiiLOTUS Database
Undaria pinnatifidaFooDB
Vaccinium
Vaccinium angustifolium
Vaccinium angustifolium X Vaccinium corymbosum
Vaccinium arboreum
Vaccinium corymbosumFooDB
Vaccinium deliciosum
Vaccinium dunalianumLOTUS Database
Vaccinium elliottii
Vaccinium macrocarpon
Vaccinium myrtilloides
Vaccinium myrtillus
Vaccinium ovalifolium
Vaccinium ovatum
Vaccinium oxycoccos
Vaccinium parvifolium
Vaccinium reticulatum
Vaccinium stamineum
Vaccinium uliginosum
Vaccinium vitis-idaea
Valerianella locustaFooDB
Vanilla
Verbena officinalis
Viburnum edule
Vicia fabaFooDB
Vicia sativaLOTUS Database
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellata
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
Virola surinamensisFooDB
Vitellaria paradoxaFooDB
VitisFooDB
Vitis aestivalis
Vitis labrusca
Vitis rotundifolia
Vitis viniferaLOTUS Database
Vitis vinifera L.FooDB
Xanthosoma sagittifolium
Xiphias gladiusFooDB
Youngia japonicaLOTUS Database
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquatica
Ziziphus zizyphus
Zoarces americanusFooDB
Zyzzya fuliginosa-
Species Where Detected
Species NameSourceReference
Escherichia coli K12KNApSAcK Database
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Pleurocybella porrigensKNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point230 °CNot Available
Boiling Point269.00 to 270.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility13.4 mg/mL at 25 °CYalkowsky, S. H., & Dannenfelser, R. M. (1992). Aquasol database of aqueous solubility. College of Pharmacy, University of Arizona, Tucson, AZ, 189.
LogP-1.06Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP-1.1ALOGPS
logP-1.1ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.11 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.2 m³·mol⁻¹ChemAxon
Polarizability21.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000929
DrugBank IDDB00150
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002250
KNApSAcK IDC00001396
Chemspider ID6066
KEGG Compound IDC00078
BioCyc IDTRP
BiGG ID33772
Wikipedia LinkTryptophan
METLIN ID5879
PubChem Compound6305
PDB IDNot Available
ChEBI ID16828
Good Scents IDrw1027851
References
General References
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  2. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
  3. Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. [PubMed:8884658 ]
  4. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. [PubMed:15911239 ]
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  7. Buczko W, Cylwik D, Stokowska W: [Metabolism of tryptophan via the kynurenine pathway in saliva]. Postepy Hig Med Dosw (Online). 2005;59:283-9. [PubMed:15995595 ]
  8. Heyes MP, Saito K, Crowley JS, Davis LE, Demitrack MA, Der M, Dilling LA, Elia J, Kruesi MJ, Lackner A, et al.: Quinolinic acid and kynurenine pathway metabolism in inflammatory and non-inflammatory neurological disease. Brain. 1992 Oct;115 ( Pt 5):1249-73. [PubMed:1422788 ]
  9. Koskiniemi M, Laakso J, Kuurne T, Laipio M, Harkonen M: Indole levels in human lumbar and ventricular cerebrospinal fluid and the effect of L-tryptophan administration. Acta Neurol Scand. 1985 Feb;71(2):127-32. [PubMed:2580417 ]
  10. Jonas AJ, Butler IJ: Circumvention of defective neutral amino acid transport in Hartnup disease using tryptophan ethyl ester. J Clin Invest. 1989 Jul;84(1):200-4. [PubMed:2472426 ]
  11. Guchhait RB, Janson C, Price WH: Validity of plasma factor in schizophrenia as measured by tryptophan uptake. Biol Psychiatry. 1975 Jun;10(3):303-14. [PubMed:49200 ]
  12. Kennedy JS, Gwirtsman HE, Schmidt DE, Johnson BW, Fielstein E, Salomon RM, Shiavi RG, Ebert MH, Parris WC, Loosen PT: Serial cerebrospinal fluid tryptophan and 5-hydroxy indoleacetic acid concentrations in healthy human subjects. Life Sci. 2002 Aug 23;71(14):1703-15. [PubMed:12137916 ]
  13. Bender KI, Lutsevich NF, Lutsevich AN, Kupchikov VV: [Endogenous metabolites as modulators of the transport of drugs by serum albumin]. Farmakol Toksikol. 1990 May-Jun;53(3):72-80. [PubMed:2201566 ]
  14. Heiman-Patterson TD, Bird SJ, Parry GJ, Varga J, Shy ME, Culligan NW, Edelsohn L, Tatarian GT, Heyes MP, Garcia CA, et al.: Peripheral neuropathy associated with eosinophilia-myalgia syndrome. Ann Neurol. 1990 Oct;28(4):522-8. [PubMed:2174666 ]
  15. Talbert AM, Tranter GE, Holmes E, Francis PL: Determination of drug-plasma protein binding kinetics and equilibria by chromatographic profiling: exemplification of the method using L-tryptophan and albumin. Anal Chem. 2002 Jan 15;74(2):446-52. [PubMed:11811421 ]
  16. Dunner DL, Heiber S, Perel JM: The effect of L-tryptophan administration on the concentration of probenecid in plasma and cerebrospinal fluid in patients. Psychopharmacology (Berl). 1977 Aug 16;53(3):305-8. [PubMed:408860 ]
  17. George CF, Millar TW, Hanly PJ, Kryger MH: The effect of L-tryptophan on daytime sleep latency in normals: correlation with blood levels. Sleep. 1989 Aug;12(4):345-53. [PubMed:2669092 ]
  18. Gutsche B, Grun C, Scheutzow D, Herderich M: Tryptophan glycoconjugates in food and human urine. Biochem J. 1999 Oct 1;343 Pt 1:11-9. [PubMed:10493906 ]
  19. Milburn DS, Myers CW: Tryptophan toxicity: a pharmacoepidemiologic review of eosinophilia-myalgia syndrome. DICP. 1991 Nov;25(11):1259-62. [PubMed:1763543 ]
  20. 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 ]
  21. Guo L, Schurink B, Roos E, Nossent EJ, Duitman JW, Vlaar AP, van der Valk P, Vaz FM, Yeh SR, Geeraerts Z, Dijkhuis A, van Vught L, Bugiani M, Lutter R: Indoleamine 2,3-dioxygenase (IDO)-1 and IDO-2 activity and severe course of COVID-19. J Pathol. 2022 Mar;256(3):256-261. doi: 10.1002/path.5842. Epub 2022 Jan 10. [PubMed:34859884 ]