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Showing Compound L-Tryptophan (FDB002250)

Record Information
Version1.0
Creation date2010-04-08 22:05:18 UTC
Update date2024-11-29 22:27:53 UTC
Primary IDFDB002250
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Tryptophan
DescriptionL-Tryptophan, also known as Trp or W, 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. L-Tryptophan is a very strong basic compound (based on its pKa). L-Tryptophan exists in all living species, ranging from bacteria to humans. Within humans, L-tryptophan participates in a number of enzymatic reactions. In particular, L-tryptophan can be converted into n'-formylkynurenine through the action of the enzyme tryptophan 2,3-dioxygenase. In addition, L-tryptophan and tetrahydrobiopterin can be converted into 5-hydroxy-L-tryptophan and 4a-hydroxytetrahydrobiopterin through its interaction with the enzyme tryptophan 5-hydroxylase 1. The L-enantiomer of tryptophan. In humans, L-tryptophan is involved in tryptophan metabolism. Outside of the human body, L-Tryptophan is found, on average, in the highest concentration within a few different foods, such as caseins, steller sea lions, and evening primroses and in a lower concentration in thunnus, kefirs, and garden onions. L-Tryptophan has also been detected, but not quantified in, several different foods, such as thistles, gelatins, garden onion (var.), alpine sweetvetchs, and remoulades. This could make L-tryptophan a potential biomarker for the consumption of these foods.
CAS Number73-22-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
(S)-(-)-Tryptophanbiospider
(S)-α-Amino-1H-indole-3-propanoic acidbiospider
(S)-2-Amino-3-(1H-indol-3-yl)propanoic acidbiospider
(S)-a-amino-b-(3-Indolyl)-propionateGenerator
(S)-a-amino-b-(3-Indolyl)-propionic acidGenerator
(S)-alpha-amino-beta-(3-Indolyl)-propionateGenerator
(S)-Tryptophan 1H-Indole-3-alanine, (S)-biospider
(S)-α-amino-1H-indole-3-propanoateGenerator
(S)-α-amino-1H-indole-3-propanoic acidGenerator
(S)-α-amino-β-(3-indolyl)-propionateGenerator
(S)-α-amino-β-(3-indolyl)-propionic acidGenerator
1H-Indole-3-alanine, (S)-biospider
1H-Indole-3-propanoic acid, α-amino-, (S)-biospider
1H-Indole-3-propanoic acid, alpha-amino-, (S)-biospider
2-amino-3-IndolylpropanoateHMDB
2-amino-3-Indolylpropanoic acidHMDB
alpha-Amino-3-indolepropionic acid, L-biospider
L-(-)-Tryptophanebiospider
L-α-Amino-3-indolepropionic acidbiospider
L-α-Aminoindole-3-propionic acidbiospider
L-β-3-Indolylalaninebiospider
L-a-Aminoindole-3-propionic acidbiospider
L-Alanine, 3-(1H-indol-3-yl)-biospider
L-Tryptophan (9CI)biospider
L-β-3-indolylalanineGenerator
Lopac-t-0254HMDB
Tryptophan, 9CI, 8CI, USAN; L-formdb_source
Tryptophan, L- (8CI)biospider
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
Chemical FormulaC11H12N2O2
IUPAC name(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
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 KeyQIVBCDIJIAJPQS-VIFPVBQESA-N
Isomeric SMILESN[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O
Average Molecular Weight204.2252
Monoisotopic Molecular Weight204.089877638
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Biological role:

Foods
  • Dairy products
  • Eggs
  • Meats

    • Grains:

    Nuts and legumes:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 64.69%; H 5.92%; N 13.72%; O 15.67%DFC
    Melting PointMp ca. 282° dec.DFC
    Boiling PointNot Available
    Experimental Water Solubility13.4 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
    Experimental logP-1.06HANSCH,C ET AL. (1995)
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical Rotation[a]21D -5.7 (5M HCl)DFC
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MSL-Tryptophan, 3 TMS, GC-MS Spectrumsplash10-0udi-0190000000-feaec8547634dddcad8cSpectrum
    GC-MSL-Tryptophan, 3 TMS, GC-MS Spectrumsplash10-0udi-0390000000-45a6c4fd79081597d44aSpectrum
    GC-MSL-Tryptophan, non-derivatized, GC-MS Spectrumsplash10-0udi-0290000000-34f7274f31a4cb321a0bSpectrum
    GC-MSL-Tryptophan, 3 TMS, GC-MS Spectrumsplash10-0fk9-9270000000-9761607cbe821f87f172Spectrum
    GC-MSL-Tryptophan, 1 TMS, GC-MS Spectrumsplash10-001i-0900000000-3faeed7ad32e1755c03cSpectrum
    GC-MSL-Tryptophan, 3 TMS, GC-MS Spectrumsplash10-0udi-0290000000-9c57a732e337fade3cb6Spectrum
    GC-MSL-Tryptophan, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-d054a214c1717940989fSpectrum
    GC-MSL-Tryptophan, non-derivatized, GC-MS Spectrumsplash10-0udi-0290000000-9860799c854e5c9ac1c7Spectrum
    GC-MSL-Tryptophan, non-derivatized, GC-MS Spectrumsplash10-0udi-0190000000-feaec8547634dddcad8cSpectrum
    GC-MSL-Tryptophan, non-derivatized, GC-MS Spectrumsplash10-0udi-0390000000-45a6c4fd79081597d44aSpectrum
    GC-MSL-Tryptophan, non-derivatized, GC-MS Spectrumsplash10-0udi-0290000000-34f7274f31a4cb321a0bSpectrum
    GC-MSL-Tryptophan, non-derivatized, GC-MS Spectrumsplash10-0udi-3729000000-86129db57aaf1a245f93Spectrum
    GC-MSL-Tryptophan, non-derivatized, GC-MS Spectrumsplash10-0fk9-9270000000-9761607cbe821f87f172Spectrum
    GC-MSL-Tryptophan, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-3faeed7ad32e1755c03cSpectrum
    GC-MSL-Tryptophan, non-derivatized, GC-MS Spectrumsplash10-0udi-0290000000-9c57a732e337fade3cb6Spectrum
    Predicted GC-MSL-Tryptophan, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0560-4900000000-fa932bc4cffed0ca66b7Spectrum
    Predicted GC-MSL-Tryptophan, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00e9-9560000000-6829a8b2a2096883999fSpectrum
    Predicted GC-MSL-Tryptophan, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSL-Tryptophan, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSL-Tryptophan, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSL-Tryptophan, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSL-Tryptophan, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSL-Tryptophan, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0910000000-db5439a5499b198817202012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014m-0900000000-cc4a579a29d19a1c0d442012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kf-3900000000-a931a9df4c855603d06e2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0290000000-5fa576241f151a3a01a22012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-417ea0b6e4e18e5fbde12012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-38f5ce97d594f3e3f12d2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-783ffff22f31096f238f2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0290000000-3ced9d310dda312f85822012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-a050919a36b995d345532012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-1ddec73daead0ffadce42012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-a8c9c60f075a675f66292012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0290602010-c09c931538bff74ac4002012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-0fed327c2a56f556e04c2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0090000000-98ec1c2c012e58eab9242012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0090000000-fc77784da5d9b288d7512012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0290601010-d6f94902c0cf639cb7bc2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-27633a4f7ecfac45c7302012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0090000000-ee6cb8392b2e8d644bc12012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-d81c86eceee1c9824b022012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0190000000-0e8b883dc8ab06c89d772012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0uxu-2940000000-cb35b9680612e19d8b3a2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-2900000000-7cc592351cc616b1d75f2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-1900000000-987615a0add5eb2c31692012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-1900000000-f150d9d1e19c72d337a82012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4r-0690000000-ea2d79df0b56be85abdd2012-08-31View Spectrum
    NMR
    TypeDescriptionView
    1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)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)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID6066
    ChEMBL IDCHEMBL54976
    KEGG Compound IDC00078
    Pubchem Compound ID6305
    Pubchem Substance IDNot Available
    ChEBI ID16828
    Phenol-Explorer IDNot Available
    DrugBank IDDB00150
    HMDB IDHMDB00929
    CRC / DFC (Dictionary of Food Compounds) IDCHP14-U:CHP19-Z
    EAFUS ID3777
    Dr. Duke IDL-TRYPTOPHAN|TRYPTOPHAN
    BIGG ID33772
    KNApSAcK IDC00001396
    HET IDTRP
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDTryptophan
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    Analgesic35480 An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
    Anti-anxiety52217 An agent that reduces anxiety symptoms, commonly used in managing anxiety disorders, by modulating neurotransmitters such as GABA and serotonin, promoting relaxation and calming effects, with key medical uses including treatment of generalized anxiety, panic disorders, and social anxiety.DUKE
    Anti-dementia52217 An agent that slows or prevents cognitive decline, reducing symptoms of dementia. It plays a biological role in neuroprotection, enhancing neuronal function and survival. Therapeutically, it is used to manage Alzheimer's disease, vascular dementia, and other neurodegenerative disorders, improving memory, cognition, and daily functioning.DUKE
    Anti depressant52217 An agent that regulates mood, reducing symptoms of depression and anxiety by altering neurotransmitter levels in the brain, commonly used in managing depression, anxiety disorders, and other mood disorders.DUKE
    Anti dyskineticAn agent that relieves or prevents dyskinesia, improving voluntary movement. It plays a biological role in regulating motor function, and has therapeutic applications in managing Parkinson's disease, Huntington's disease, and other movement disorders, reducing involuntary movements and improving motor control.DUKE
    Anti hypertensive52217 An agent that lowers blood pressure, reducing the risk of cardiovascular disease. It plays a biological role in relaxing blood vessels, decreasing cardiac workload, and improving blood flow. Therapeutically, it's used to manage hypertension, heart failure, and stroke, with key medical applications in preventing organ damage and improving overall cardiovascular health.DUKE
    Anti-insomniac52217 An agent that promotes sleep, reducing insomnia symptoms. It regulates the body's sleep-wake cycle, commonly used in managing sleep disorders, such as chronic insomnia, and improving overall sleep quality.DUKE
    Anti-manicAn agent that stabilizes mood by controlling symptoms of mania, used to manage bipolar disorder, reducing excessive excitement and impulsivity, and preventing manic episodes.DUKE
    Anti-menopausal52217 An agent that alleviates menopausal symptoms, regulating hormonal balance and reducing discomfort. Therapeutically, it is used to manage hot flashes, night sweats, and mood changes, improving quality of life for menopausal women. Key medical uses include hormone replacement therapy and treatment of menopause-related disorders.DUKE
    Anti-migraine52217 An agent that alleviates migraine symptoms, commonly used to treat and prevent migraine headaches by constricting blood vessels and blocking pain pathways, providing relief from severe headaches, nausea, and sensitivity to light and sound.DUKE
    Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
    Anti-Parkinsonian48407 An agent that alleviates symptoms of Parkinson's disease, enhancing dopamine levels and improving motor function, commonly used to manage tremors, rigidity, and bradykinesia in neurodegenerative disorders.DUKE
    Anti phenylketonuric52217 An agent that reduces phenylalanine levels, managing phenylketonuria (PKU) by inhibiting enzymes involved in phenylalanine metabolism, thereby preventing intellectual disability and other complications associated with the condition.DUKE
    Anti prostaglandin49020 An agent that inhibits prostaglandin production, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and post-surgical pain, by blocking prostaglandin-mediated responses, providing relief from inflammation and discomfort.DUKE
    Anti psychotic35476 An agent that reduces psychotic symptoms, commonly used in managing schizophrenia, bipolar disorder, and other mental health conditions by blocking dopamine receptors in the brain, thereby alleviating hallucinations, delusions, and disordered thinking.DUKE
    Anti-rheumatic52217 An agent that reduces inflammation and alleviates symptoms of rheumatic diseases, such as arthritis. It plays a biological role in modulating the immune system and inhibiting pro-inflammatory pathways. Therapeutically, anti-rheumatics are used to manage conditions like rheumatoid arthritis, lupus, and osteoarthritis, reducing pain, swelling, and joint damage. Key medical uses include slowing disease progression and improving quality of life for patients with chronic rheumatic conditions.DUKE
    Anti-scoliotic52217 An agent that prevents or reduces the progression of scoliosis, a lateral curvature of the spine. It plays a biological role in maintaining spinal alignment and stability. Therapeutically, it is used to manage scoliosis, particularly in children and adolescents, to prevent deformity and promote proper spinal growth, reducing the need for surgical intervention.DUKE
    Carcinogenic50903 An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment.DUKE
    EssentialA substance crucial for a specific biological process or condition, playing a vital role in maintaining health. Therapeutically, essentials are used to prevent or treat deficiencies, with key medical applications including nutrition, hormone regulation, and disease prevention, ultimately supporting overall well-being.DUKE
    HypnoticAn agent that induces sleep, used to treat insomnia and facilitate surgical anesthesia, playing a key role in regulating sleep patterns and providing therapeutic relief for sleep disorders.DUKE
    Hypoglycemic35526 An agent that lowers blood glucose levels, playing a crucial role in glucose metabolism. Therapeutically, it is used to manage diabetes and insulin resistance, with key medical applications in treating type 1 and 2 diabetes, and preventing diabetic complications.DUKE
    HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
    Insulinase inhibitor23924 An agent that blocks the activity of insulinase, an enzyme that breaks down insulin, thereby increasing insulin levels and activity. It has therapeutic applications in managing diabetes and improving glucose metabolism, with key medical uses in treating type 1 and 2 diabetes.DUKE
    InsulinotonicAn agent that enhances insulin secretion, improving glucose uptake and utilization. It plays a biological role in regulating blood sugar levels. Therapeutically, insulinotonic agents are used to manage type 2 diabetes, increasing insulin sensitivity and reducing glucose production in the liver, thereby lowering blood glucose levels.DUKE
    Monoamine precursorAn amino acid (e.g., phenylalanine, tyrosine, tryptophan) that serves as a building block for monoamine neurotransmitters like serotonin, norepinephrine, and dopamine, playing a crucial role in mood regulation and therapeutic applications in managing depression, anxiety, and other neurological disorders.DUKE
    ProlactinogenicAn agent that stimulates the production of prolactin, a hormone involved in lactation and breast development, with potential therapeutic applications in treating infertility and lactation disorders, and key medical uses in inducing milk production and managing hormonal imbalances.DUKE
    Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.DUKE
    Serotoninergic48278 An agent that modulates serotonin activity, regulating mood, appetite, and sleep. It has therapeutic applications in treating depression, anxiety, and mood disorders, with key medical uses including antidepressants, anxiolytics, and anti-migraine medications.DUKE
    Tumor promoter50903 A substance that enhances the growth and proliferation of cancer cells, often used in research to study cancer development. Therapeutically, understanding tumor promoters informs cancer prevention and treatment strategies, with applications in oncology for developing targeted therapies to inhibit tumor growth and progression.DUKE
    Enzymes
    NameGene NameUniProt ID
    Aromatic-L-amino-acid decarboxylaseDDCP20711
    Tryptophan 5-hydroxylase 1TPH1P17752
    Tryptophan 5-hydroxylase 2TPH2Q8IWU9
    Tryptophan--tRNA ligase, cytoplasmicWARSP23381
    Tryptophan--tRNA ligase, mitochondrialWARS2Q9UGM6
    Pathways
    NameSMPDB LinkKEGG Link
    Transcription/TranslationSMP00019 Not Available
    Tryptophan MetabolismSMP00063 map00380
    Metabolism and Physiological Effects of Indole Acetic AcidSMP0123235 Not Available
    Metabolism and Physiological Effects of Indoxyl SulfateSMP0123237 Not Available
    Metabolism and Physiological Effects of Indoxyl glucuronide SMP0123239 Not Available
    Metabolism and Physiological Effects of Quinolinic Acid SMP0123249 Not Available
    Metabolism and Physiological Effects of Kynurenic Acid SMP0123300 Not Available
    Metabolism and Physiological Effects of Indoxyl glucoside (indican) SMP0124742 Not Available
    Metabolism and Physiological Effects of KynurenineSMP0125524 Not Available
    Metabolism and Physiological Effects of N-AcetyltryptophanSMP0126721 Not Available
    Metabolism and Physiological Effects of Indolelactic AcidSMP0126749 Not Available
    Metabolism and Physiological Effects of Indolelacetyl glutamineSMP0126755 Not Available
    Metabolism and Physiological Effects of 2-Aminobenzoic acidSMP0126869 Not Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
    — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).