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L-Tryptophan (PC000113)

Record Information
Version1.0
Creation date2015-10-09 22:28:33 UTC
Update date2017-01-19 02:36:13 UTC
FoodComEx IDPC000113
FoodDB RecordFDB002250
Chemical Information
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
(-)-Tryptophanbiospider
(2S)-2-Amino-3-(1H-indol-3-yl)propanoatebiospider
(2S)-2-Amino-3-(1H-indol-3-yl)propanoic acidbiospider
(L)-Tryptophanbiospider
(S)-(-)-Tryptophanbiospider
(S)-α-Amino-1H-indole-3-propanoic acidbiospider
(S)-1H-Indole-3-alaninebiospider
(S)-2-Amino-3-(1H-indol-3-yl)propanoic acidbiospider
(S)-2-Amino-3-(3-indolyl)propionic acidbiospider
(S)-a-Amino-1H-indole-3-propanoatebiospider
(S)-a-Amino-1H-indole-3-propanoic acidbiospider
(S)-a-amino-b-(3-Indolyl)-propionateGenerator
(S)-a-amino-b-(3-Indolyl)-propionic acidGenerator
(S)-a-Amino-b-indolepropionatebiospider
(S)-a-Amino-b-indolepropionic acidbiospider
(S)-a-Aminoindole-3-propionatebiospider
(S)-a-Aminoindole-3-propionic acidbiospider
(S)-alpha-Amino-1H-indole-3-propanoatebiospider
(S)-alpha-Amino-1H-indole-3-propanoic acidbiospider
(S)-alpha-amino-beta-(3-Indolyl)-propionateGenerator
(S)-alpha-Amino-beta-(3-indolyl)-propionic acidbiospider
(S)-alpha-Amino-beta-indolepropionatebiospider
(S)-alpha-Amino-beta-indolepropionic acidbiospider
(S)-alpha-Aminoindole-3-propionatebiospider
(S)-alpha-Aminoindole-3-propionic acidbiospider
(S)-Tryptophanbiospider
(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
1-beta-3-IndolylalanineHMDB
1beta-3-IndolylalanineHMDB
1H-Indole-3-alanineHMDB
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
3-(1H-indol-3-yl)-L-AlanineHMDB
3-indol-3-YlalanineHMDB
alpha-Amino-3-indolepropionic acid, L-biospider
alpha-Aminoindole-3-propionic acidHMDB
Alpha'-amino-3-indolepropionic acidHMDB
ArdeytropinHMDB
H-TRP-OHHMDB
Indole-3-alanineHMDB
KalmaHMDB
L-(-)-TryptophanChEBI
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-alpha-Amino-3-indolepropionic acidbiospider
L-alpha-Aminoindole-3-propionic acidbiospider
L-b-3-IndolylalanineGenerator
L-beta-3-IndolylalanineChEBI
L-TryptofanHMDB
L-Tryptophan (9CI)biospider
L-TryptophaneHMDB
L-β-3-indolylalanineGenerator
Lopac-t-0254HMDB
LyphanHMDB
OptimaxHMDB
PacitronHMDB
SedanoctHMDB
TriptofanoHMDB
TrofanHMDB
TrpChEBI
TryptacinHMDB
TryptanHMDB
Tryptophan, 9CI, 8CI, USAN; L-formdb_source
Tryptophan, L- (8CI)biospider
TryptophaneHMDB
TryptophanumHMDB
WChEBI
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
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-1.06HANSCH,C ET AL. (1995)
Experimental Water Solubility13.4 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting PointMp ca. 282° dec.DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 2 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci K248
Glentham GM0674
Glentham GM0192
MetaSci HMDB0000929
Sigma-Aldrich HMDB0000929
Toronto Research Chemicals T947210