| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:08:38 -0700 |
| HMDB ID |
HMDB00472 |
| Secondary Accession Numbers |
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| Metabolite Identification |
|---|
| Common Name |
5-Hydroxy-L-tryptophan |
| 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. (PMID: 9295177 , 17240182 , 16023217 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- (+-)-5-Hydroxytryptophan
- (S)-5-Hydroxytryptophan
- 5-Hydroxy-L-Tryptophan
- 5-Hydroxy-tryptophan
- 5-Hydroxyl-L-tryptophan
- 5-Hydroxytryptophan
- 5-Hydroxytryptophan L form
- 5-Hydroxytryptophan L-form
- Cincofarm
- Hydroxytryptophan
- L-5-Hydroxytryptophan
- Levothym
- Levotinine
- Oxitriptan
- Oxyfan
- Oxytryptophan
- Pretonine
- Quietim
- Serotonyl
- Telesol
- Triptene
|
| Chemical Formula |
C11H12N2O3 |
| Average Molecular Weight |
220.2246 |
| Monoisotopic Molecular Weight |
220.08479226 |
| IUPAC Name |
2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid |
| Traditional IUPAC Name |
(+-)-5-hydroxytryptophan |
| CAS Registry Number |
4350-09-8 |
| 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 Key |
LDCYZAJDBXYCGN-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Amino Acids, Peptides, and Analogues |
| Class |
Amino Acids and Derivatives |
| Sub Class |
Alpha Amino Acids and Derivatives |
| Other Descriptors |
- Aromatic Heteropolycyclic Compounds
- amino acid zwitterion(ChEBI)
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| Substituents |
- Carboxylic Acid
- Indole
- Indolyl Carboxylic Acid Derivative
- Phenol
- Phenol Derivative
- Primary Aliphatic Amine (Alkylamine)
- Pyrrole
- Serotonin
- Tryptamine
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| Direct Parent |
Alpha Amino Acids and Derivatives |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
- Protein synthesis, amino acid biosynthesis
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| Application |
Not Available |
| Cellular locations |
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| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
293 - 298 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
-2.051 |
Not Available |
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| Predicted Properties |
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| Spectra |
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| Biological Properties |
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| Cellular Locations |
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| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Urine
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| Tissue Location |
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| Pathways |
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| Normal Concentrations |
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| Blood |
Detected and Quantified |
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0.018 +/- 0.0027 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.005 (0.00-0.010) uM |
Infant (0-1 year old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.0078 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
DB02959 |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB006231 |
| KNApSAcK ID |
C00001371 |
| Chemspider ID |
141 |
| KEGG Compound ID |
C01017 |
| BioCyc ID |
5-HYDROXY-TRYPTOPHAN |
| BiGG ID |
36630 |
| Wikipedia Link |
5-HTP |
| NuGOwiki Link |
HMDB00472 |
| Metagene Link |
HMDB00472 |
| METLIN ID |
Not Available |
| PubChem Compound |
144 |
| PDB ID |
Not Available |
| ChEBI ID |
28171 |
| References |
|---|
| Synthesis Reference |
Boroda, E.; Rakowska, S.; Kanski, R.; Kanska, M. Enzymatic synthesis of L-tryptophan and 5'-hydroxy-L-tryptophan labeled with deuterium and tritium at the a-carbon position. Journal of Labelled Compounds & Radiopharmaceuticals (2003), 46(8), 691-698. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Magnussen I, Van Woert MH: Human pharmacokinetics of long term 5-hydroxytryptophan combined with decarboxylase inhibitors. Eur J Clin Pharmacol. 1982;23(1):81-6.
Pubmed: 6182005
- Li Kam Wa TC, Freestone S, Samson RR, Johnson NR, Lee MR: A comparison of the renal and neuroendocrine effects of two 5-hydroxytryptamine renal prodrugs in normal man. Clin Sci (Lond). 1993 Nov;85(5):607-14.
Pubmed: 8287650
- Li Kam Wa TC, Freestone S, Samson RR, Johnston NR, Lee MR: Renal metabolism and effects of the glutamyl derivatives of L-dopa and 5-hydroxytryptophan in man. Clin Sci (Lond). 1996 Aug;91(2):177-85.
Pubmed: 8795441
- 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. 1997;104(4-5):451-9.
Pubmed: 9295177
- 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.
Pubmed: 17240182
- 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.
Pubmed: 16023217
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4.
Pubmed: 19212411
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