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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:36:33 UTC
Update Date2018-05-20 02:21:03 UTC
HMDB IDHMDB0030396
Secondary Accession Numbers
  • HMDB30396
Metabolite Identification
Common Name(±)-Tryptophan
Description(±)-Tryptophan is a dietary supplement, nutrient.Tryptophan is one of the 20 standard amino acids, as well as an essential amino acid in the human diet. Only the L-stereoisomer of tryptophan is used in structural or enzyme proteins, but the D-stereoisomer is occasionally found in naturally produced peptides (for example, the marine venom peptide contryphan). (Wikipedia
Structure
Thumb
Synonyms
ValueSource
2-amino-3-(1H-indol-3-yl)Propanoic acidChEBI
alpha-amino-beta-(3-Indolyl)-propionic acidChEBI
alpha-amino-beta-3-Indolepropionic acidChEBI
beta-3-IndolylalanineChEBI
HTRPChEBI
TriptofanoChEBI
TrpChEBI
TryptophaneChEBI
WChEBI
2-amino-3-(1H-indol-3-yl)PropanoateGenerator
a-amino-b-(3-Indolyl)-propionateGenerator
a-amino-b-(3-Indolyl)-propionic acidGenerator
alpha-amino-beta-(3-Indolyl)-propionateGenerator
α-amino-β-(3-indolyl)-propionateGenerator
α-amino-β-(3-indolyl)-propionic acidGenerator
a-amino-b-3-IndolepropionateGenerator
a-amino-b-3-Indolepropionic acidGenerator
alpha-amino-beta-3-IndolepropionateGenerator
α-amino-β-3-indolepropionateGenerator
α-amino-β-3-indolepropionic acidGenerator
b-3-IndolylalanineGenerator
β-3-indolylalanineGenerator
(+-)-TryptophanHMDB
(+/-)-2-amino-3-(3-indolyl)propionic acidHMDB
(+/-)-alpha-amino-3-indolepropionic acidHMDB
DL-2-amino-3-Indolepropionic acidHMDB
DL-3beta-IndolylalanineHMDB
DL-alpha-amino-3-Indolepropionic acidHMDB
DL-TryptophanHMDB
Racemic tryptophanHMDB
Chemical FormulaC11H12N2O2
Average Molecular Weight204.2252
Monoisotopic Molecular Weight204.089877638
IUPAC Name2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional Nametryptophan(.)
CAS Registry Number54-12-6
SMILES
NC(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)
InChI KeyQIVBCDIJIAJPQS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These 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
  • 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

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point293 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.05Not Available
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
Polarizability21.19 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00lr-1940000000-7d24b93f0df6ee59c1cfView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-0290000000-1a8228e2b523be1ae691View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0390000000-bf55780347500228fa0aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fsi-0930000000-a768dbcdd61c5ddfc7ffView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-057i-5900000000-19287f7752709aae95d9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9560000000-6829a8b2a2096883999fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0290000000-177c39ffff7351ae58e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0920000000-31f2bf06783a35cb177eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0zfr-0890000000-70571859405f22f7726dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0uxr-1960000000-4794df4619ca53da8a26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0zfr-0790000000-71f96432b70be90e3e76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-678ef44eecd71f98f4bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-1910000000-3b90b4510b3064cd8257View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-30198ffd85182eef6dbbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0190000000-2319c76338ccc72cea91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0690000000-2d67e3b24d52541620dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0390000000-32f53d15608910742122View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0gb9-1940000000-4d8b6d43d6dc47a0a53cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-672eea5be46683e01aa3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-b167000b756e70598ebbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0290000000-f83d06a826ee6963c139View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0190000000-af6a41a358461c4944d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-1930000000-fe537846c01a00076d1bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0uxr-1980000000-bc34bf853c58cd38c9ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0290000000-fff893c43aa27aebf582View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0920000000-825129a9df3095f19bd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0900000000-142753592a64d1b21225View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-4f3eacbba35070501781View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3490000000-de7027f417d1320c2b85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9830000000-415cd821aca8befd3e58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-9600000000-8e10a14ed0f3f1b8fb23View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-c6c45a933a953618aa8cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified15.5307 +/- 5.778 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified14.8138 +/- 6.3068 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified11.3657 +/- 8.4904 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002251
KNApSAcK IDC00001396
Chemspider ID1116
KEGG Compound IDC00806
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTryptophan
METLIN IDNot Available
PubChem Compound1148
PDB IDNot Available
ChEBI ID27897
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. BARENBOIM GM: [Brief-duration fluorescence of DLtryptophan in frozen solutions]. Biofizika. 1962;7:227-32. [PubMed:13864966 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .