ContaminantDB: 5-Hydroxy-L-tryptophan

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:16:56 UTC

Update Date

2026-04-06 01:07:37 UTC

Accession Number

CHEM003258

Identification

Common Name

5-Hydroxy-L-tryptophan

Class

Small Molecule

Description

5-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. (1, 2, 3).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Animal Toxin
Antidepressive Agent, Second-Generation
Drug
Food Toxin
Metabolite
Natural Compound
Nutraceutical
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-5-Hydroxytryptophan	ChEBI
5-HTP	ChEBI
5-Hydroxy-DL-tryptophan	ChEBI
5-Hydroxytryptophan DL-form	ChEBI
DL-5-HTP	ChEBI
DL-5-Hydroxytryptophan	ChEBI
(S)-5-Hydroxytryptophan	HMDB
5-Hydroxy-tryptophan	HMDB
5-Hydroxyl-L-tryptophan	HMDB
5-Hydroxytryptophan	HMDB, MeSH
5-Hydroxytryptophan L form	HMDB
5-Hydroxytryptophan L-form	HMDB
Cincofarm	HMDB
Hydroxytryptophan	HMDB, MeSH
L-5-Hydroxytryptophan	HMDB
Levothym	HMDB
Levotinine	HMDB
Oxitriptan	HMDB, MeSH
Oxyfan	HMDB
Oxytryptophan	HMDB, MeSH
Pretonine	HMDB
Quietim	HMDB
Serotonyl	HMDB
Telesol	HMDB
Triptene	HMDB
5 Hydroxytryptophan	MeSH
5-Hydroxy- tryptophan	MeSH
Tryptophan, 5 hydroxy	MeSH

Chemical Formula

C₁₁H₁₂N₂O₃

Average Molecular Mass

220.225 g/mol

Monoisotopic Mass

220.085 g/mol

CAS Registry Number

4350-09-8

IUPAC Name

2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

Traditional Name

DL-5-hydroxytryptophan

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 Key

LDCYZAJDBXYCGN-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Serotonins

Alternative Parents

Substituents

Serotonin
Indolyl carboxylic acid derivative
Alpha-amino acid
Alpha-amino acid or derivatives
Hydroxyindole
3-alkylindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Amino acid
Amino acid or derivatives
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Primary amine
Carbonyl group
Organic nitrogen compound
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxytryptophan (CHEBI:28171 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Blood
Brain
Prostate

Pathways

Name	SMPDB Link	KEGG Link
Tryptophan Metabolism	SMP00063	map00380
Aromatic L-Aminoacid Decarboxylase Deficiency	SMP00170	Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	295-297°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.63 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.15	ChemAxon
pKa (Strongest Basic)	9.18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.34 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	58.18 m³·mol⁻¹	ChemAxon
Polarizability	22.03 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0390000000-3c19ae217ad78448c30f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0097-5920000000-eb294b94875b74adc6f8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9067000000-2ab7fbf926f4f1b43002	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0090000000-823f10e31a9f15588233	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-053r-0900000000-d763102ca4968c158d29	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-053r-0900000000-500716cec2e9f8383df7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-00rx-2930000000-9e9f041cf524d559b331	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0090000000-44c37ec15a5546b1c353	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0910000000-5e6f9e21dd30ec8c20f3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0900000000-b656dc85b8aff47fea96	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-3900000000-94c7412dbb7cb04c9f32	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0w29-0790000000-233a5164a2a4514e5bb9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fi0-0980000000-52f402588d34f0e4bf81	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0910000000-f2841345d00a265d4104	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-0900000000-df31c7e703c994b797fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2090000000-28b52756bfbd372bccf4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9460000000-093dd610b11a147c2056	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00e9-9500000000-d567d2ab0b6a5e8a8a22	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. An accumulation of 5-hydroxy-L-tryptophan in cerebrospinal fluid occurs in aromatic L-amino acid decarboxylase deficiency, accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder. 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.

Metabolism

5-Hydroxytryptophan is decarboxylated to serotonin (5-hydroxytryptamine or 5-HT) by the enzyme aromatic-L-amino-acid decarboxylase with the help of vitamin B6. This reaction occurs both in nervous tissue and in the liver.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For use as an antidepressant, appetite suppressant, and sleep aid.

Minimum Risk Level

Not Available

Health Effects

Chronically high levels of 5-hydroxytryptophan are associated with Aromatic L-Amino acid Decarboxylase Deficiency.