Record Information
Version1.0
Creation date2010-04-08 22:07:02 UTC
Update date2019-11-26 03:01:01 UTC
Primary IDFDB006231
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-Hydroxy-L-tryptophan
Description5-Hydroxy-L-tryptophan, also known as 5-HTP or levothym, belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. 5-Hydroxy-L-tryptophan exists in all living organisms, ranging from bacteria to humans. 5-Hydroxy-L-tryptophan has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), french plantains (Musa X paradisiaca), and milk (cow). This could make 5-hydroxy-L-tryptophan a potential biomarker for the consumption of these foods. 5-Hydroxy-L-tryptophan, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, colorectal cancer, and crohn's disease; 5-hydroxy-L-tryptophan has also been linked to the inborn metabolic disorder aromatic l-amino acid decarboxylase deficiency. Based on a literature review a significant number of articles have been published on 5-Hydroxy-L-tryptophan.
CAS Number4350-09-8
Structure
Thumb
Synonyms
SynonymSource
5-Hydroxytryptophan L-formChEBI
CincofarmChEBI
L-5-HydroxytryptophanChEBI
LevothymChEBI
OxitriptanChEBI
Tript-OHChEBI
Hydroxy-5 L-tryptophaneHMDB
5-HTPHMDB
HydroxytryptophanHMDB
5-HydroxytryptophanHMDB
5 HydroxytryptophanHMDB
5-Hydroxy- tryptophanHMDB
OxytryptophanHMDB
Tryptophan, 5 hydroxyHMDB
(S)-5-HydroxytryptophanHMDB
5-Hydroxyl-L-tryptophanHMDB
LevotonineHMDB
OxyfanHMDB
PretonineHMDB
QuietimHMDB
SerotonylHMDB
TelesolHMDB
TripteneHMDB
TriptumHMDB
L-5-HTPHMDB
5-Hydroxy-L-tryptophanHMDB
(+-)-5-HydroxytryptophanChEBI
5-Hydroxy-DL-tryptophanChEBI
5-Hydroxy-tryptophanHMDB
5-Hydroxytryptophan DL-formChEBI
5-Hydroxytryptophan L formHMDB
DL-5-HTPChEBI
DL-5-HydroxytryptophanChEBI
L-Tryptophan, 5-hydroxy-biospider
LevotinineHMDB
Tryptophan, 5-hydroxy-, L-biospider
Predicted Properties
PropertyValueSource
Water Solubility3.63 g/LALOGPS
logP-1.6ALOGPS
logP-1.4ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.15ChemAxon
pKa (Strongest Basic)9.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.34 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity58.18 m³·mol⁻¹ChemAxon
Polarizability22.03 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H12N2O3
IUPAC name(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
InChI IdentifierInChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1
InChI KeyLDCYZAJDBXYCGN-VIFPVBQESA-N
Isomeric SMILESN[C@@H](CC1=CNC2=C1C=C(O)C=C2)C(O)=O
Average Molecular Weight220.2246
Monoisotopic Molecular Weight220.08479226
Classification
Description Belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentSerotonins
Alternative Parents
Substituents
  • Serotonin
  • Indolyl carboxylic acid derivative
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • L-alpha-amino acid
  • Hydroxyindole
  • Indole
  • Aralkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid
  • Amino acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxide
  • 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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point293-298 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-2.051
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS5-Hydroxy-L-tryptophan, 4 TMS, GC-MS Spectrumsplash10-0006-0390000000-d4e36a90b7591787e67bSpectrum
GC-MS5-Hydroxy-L-tryptophan, 3 TMS, GC-MS Spectrumsplash10-0006-1390000000-b0af49def87c0211653cSpectrum
GC-MS5-Hydroxy-L-tryptophan, 3 TMS, GC-MS Spectrumsplash10-014i-0390000000-8b7f6cc8f51c032dd86dSpectrum
GC-MS5-Hydroxy-L-tryptophan, non-derivatized, GC-MS Spectrumsplash10-014i-0390000000-88191cf8140abf0f3205Spectrum
GC-MS5-Hydroxy-L-tryptophan, non-derivatized, GC-MS Spectrumsplash10-0006-0290000000-a30ea02ff8d4d14ba7a4Spectrum
GC-MS5-Hydroxy-L-tryptophan, non-derivatized, GC-MS Spectrumsplash10-0006-0390000000-d4e36a90b7591787e67bSpectrum
GC-MS5-Hydroxy-L-tryptophan, non-derivatized, GC-MS Spectrumsplash10-0006-1390000000-b0af49def87c0211653cSpectrum
GC-MS5-Hydroxy-L-tryptophan, non-derivatized, GC-MS Spectrumsplash10-014i-0390000000-8b7f6cc8f51c032dd86dSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00bd-4920000000-c1f07beecfc6ada179c1Spectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9044000000-9dc0e361e3885451d81fSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxy-L-tryptophan, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0790000000-a699ed429ebd1609f995Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03e9-0900000000-bbd302f8ff188f6cf93dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-053r-0900000000-6cc3ba396b1cfa8db1e6Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-053r-2900000000-90a465428eacaced71e2Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0390000000-8d1a103c7fb1b7dfa685Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-25de1fda6182de338d15Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-053r-0900000000-e8cfeeeea0f83c87c0a3Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0w29-0790000000-61308573c0d4d1caee8aSpectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0w90-0590000000-9c6aa4b5a920add9f8eaSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0930000000-074911d5bc17a486cbb0Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0uk9-0190000000-9d6cad9671c04310ac0cSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-05ox-2900000000-08b2a2c24032d96597dbSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000x-1900000000-9c83828dc6df75a0e798Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-001l-1900000000-dc720fc8e93906bb0c67Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014l-1970000000-6deb0cc19e89586090e6Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001l-0900000000-cab77201c86bda083dd0Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-053r-1900000000-b1c220623de477b387eeSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-053r-0900000000-f7c54dfcc55add0c83d6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00b9-0950000000-e3f9fbda111b2109f630Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-b21f3fecc8ae15c125deSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900000000-817e4d468ea1bf1a3bc3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2190000000-65b1ee730ae09a2cd6a5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9650000000-68d73bfc7c9dd0f880e1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9600000000-c58badf19c5cbb2f4347Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1950000000-5df9078df2a62ba2dc7eSpectrum
NMRNot Available
ChemSpider ID141
ChEMBL IDCHEMBL162789
KEGG Compound IDC01017
Pubchem Compound ID144
Pubchem Substance IDNot Available
ChEBI ID17780
Phenol-Explorer IDNot Available
DrugBank IDDB02959
HMDB IDHMDB00472
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke ID5-HYDROXY-L-TRYPTOPHAN
BIGG ID36630
KNApSAcK IDC00001371
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID5-HTP
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Aromatic-L-amino-acid decarboxylaseDDCP20711
Tryptophan 5-hydroxylase 1TPH1P17752
Tryptophan 5-hydroxylase 2TPH2Q8IWU9
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).