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Record Information
Version1.0
Creation Date2016-07-13 19:43:42 UTC
Update Date2016-07-20 20:57:06 UTC
LmdbLMDB00161
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Hydroxy-L-tryptophan
Description5-Hydroxy-L-tryptophan is an aromatic amino acid naturally produced by the body from the essential amino acid l-tryptophan. 5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. The conversion to serotonin is catalyzed by the enzyme aromatic l-amino acid decarboxylase (EC 4.1.1.28, AADC1 also known as dopa decarboxylase), an essential enzyme in the metabolism of the monoamine neurotransmitters. An accumulation of 5-Hydroxy-L-tryptophan in cerebrospinal fluid occurs in Aromatic l-amino acid decarboxylase deficiency (OMIM 608643 ), accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder but not specific 5-Hydroxy-L-tryptophan is also increased in other disorders such as in Parkinson's patients with severe postural instability and gait disorders. Confirmation of the diagnosis AADC deficiency is then required by enzyme activity measurement or genetic analysis. The amount of endogenous 5-Hydroxy-L-tryptophan available for serotonin synthesis depends on the availability of tryptophan and on the activity of various enzymes, especially tryptophan hydroxylase (EC 1.14.16.4), indoleamine 2,3-dioxygenase (EC 1.13.11.52), and tryptophan 2,3-dioxygenase. (EC 1.13.11.11, TDO). 5-Hydroxy-L-tryptophan has been used clinically for over 30 years. In addition to depression, the therapeutic administration of 5-Hydroxy-L-tryptophan has been shown to be effective in treating a wide variety of conditions, including fibromyalgia, insomnia, binge eating associated with obesity, cerebellar ataxia, and chronic headaches. 5-Hydroxy-L-tryptophan easily crosses the blood-brain barrier and effectively increases central nervous system (CNS) synthesis of serotonin. Supplementation with 5-Hydroxy-L-tryptophan is hypothesized to normalize serotonin synthesis, which is putatively related to its antidepressant properties. (PMID: 9295177 , 17240182 , 16023217 ).
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC11H12N2O3
Average Molecular Weight220.2246
Monoisotopic Molecular Weight220.08479226
IUPAC Name(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
Traditional Namehydroxytryptophan
CAS Registry Number4350-09-8
SMILES
NC(CC1=CNC2=C1C=C(O)C=C2)C(O)=O
InChI Identifier
InChI=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)
InChI KeyLDCYZAJDBXYCGN-UHFFFAOYSA-N
Chemical Taxonomy
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
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0006-0390000000-d4e36a90b7591787e67bSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0006-1390000000-b0af49def87c0211653cSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-0390000000-8b7f6cc8f51c032dd86dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0390000000-88191cf8140abf0f3205Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0290000000-a30ea02ff8d4d14ba7a4Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-0390000000-d4e36a90b7591787e67bSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-1390000000-b0af49def87c0211653cSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-0390000000-8b7f6cc8f51c032dd86dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00bd-4920000000-c1f07beecfc6ada179c1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9044000000-9dc0e361e3885451d81fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0790000000-a699ed429ebd1609f995Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03e9-0900000000-bbd302f8ff188f6cf93dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-053r-0900000000-6cc3ba396b1cfa8db1e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-053r-2900000000-90a465428eacaced71e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0390000000-8d1a103c7fb1b7dfa685Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-25de1fda6182de338d15Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-053r-0900000000-e8cfeeeea0f83c87c0a3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0w29-0790000000-61308573c0d4d1caee8aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0w90-0590000000-9c6aa4b5a920add9f8eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0930000000-074911d5bc17a486cbb0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0uk9-0190000000-9d6cad9671c04310ac0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-05ox-2900000000-08b2a2c24032d96597dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000x-1900000000-9c83828dc6df75a0e798Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-001l-1900000000-dc720fc8e93906bb0c67Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014l-1970000000-6deb0cc19e89586090e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001l-0900000000-cab77201c86bda083dd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-053r-1900000000-b1c220623de477b387eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-053r-0900000000-f7c54dfcc55add0c83d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00b9-0950000000-e3f9fbda111b2109f630Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-b21f3fecc8ae15c125deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900000000-817e4d468ea1bf1a3bc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2190000000-65b1ee730ae09a2cd6a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9650000000-68d73bfc7c9dd0f880e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9600000000-c58badf19c5cbb2f4347Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1950000000-5df9078df2a62ba2dc7eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
UrineDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDDB02959
HMDB IDHMDB0000472
FooDB IDFDB006231
Phenol Explorer IDNot Available
KNApSAcK IDC00001371
BiGG IDNot Available
BioCyc ID5-HYDROXY-TRYPTOPHAN
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link5-Hydroxytryptophan
Chemspider ID388413
ChEBI ID17780
PubChem Compound ID439280
Kegg Compound IDC00643
YMDB IDNot Available
ECMDB IDM2MDB004850
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Iacono RP, Kuniyoshi SM, Ahlman JR, Zimmerman GJ, Maeda G, Pearlstein RD: Concentrations of indoleamine metabolic intermediates in the ventricular cerebrospinal fluid of advanced Parkinson's patients with severe postural instability and gait disorders. J Neural Transm (Vienna). 1997;104(4-5):451-9. [9295177 ]
  2. Verbeek MM, Geurtz PB, Willemsen MA, Wevers RA: Aromatic L-amino acid decarboxylase enzyme activity in deficient patients and heterozygotes. Mol Genet Metab. 2007 Apr;90(4):363-9. Epub 2007 Jan 19. [17240182 ]
  3. Turner EH, Loftis JM, Blackwell AD: Serotonin a la carte: supplementation with the serotonin precursor 5-hydroxytryptophan. Pharmacol Ther. 2006 Mar;109(3):325-38. Epub 2005 Jul 14. [16023217 ]