Livestock Metabolome Database: Showing metabocard for 5-Hydroxy-L-tryptophan (LMDB00161)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:43:42 UTC

Update Date

2016-07-20 20:57:06 UTC

Lmdb

LMDB00161

Secondary Accession Numbers

None

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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Hydroxytryptophan L-form	ChEBI
Cincofarm	ChEBI
L-5-Hydroxytryptophan	ChEBI
Levothym	ChEBI
Oxitriptan	ChEBI
Tript-OH	ChEBI
Hydroxy-5 L-tryptophane	HMDB
5-HTP	HMDB
Hydroxytryptophan	HMDB
5-Hydroxytryptophan	HMDB
5 Hydroxytryptophan	HMDB
5-Hydroxy- tryptophan	HMDB
Oxytryptophan	HMDB
Tryptophan, 5 hydroxy	HMDB
(S)-5-Hydroxytryptophan	HMDB
5-Hydroxyl-L-tryptophan	HMDB
Levotonine	HMDB
Oxyfan	HMDB
Pretonine	HMDB
Quietim	HMDB
Serotonyl	HMDB
Telesol	HMDB
Triptene	HMDB
Triptum	HMDB
L-5-HTP	HMDB
5-Hydroxy-L-tryptophan	HMDB

Chemical Formula

C₁₁H₁₂N₂O₃

Average Molecular Weight

220.2246

Monoisotopic Molecular Weight

220.08479226

IUPAC Name

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

Traditional Name

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

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
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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:17780 )
5-hydroxytryptophan (CHEBI:17780 )
hydroxy-L-tryptophan (CHEBI:17780 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0006-0390000000-d4e36a90b7591787e67b	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0006-1390000000-b0af49def87c0211653c	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-014i-0390000000-8b7f6cc8f51c032dd86d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0390000000-88191cf8140abf0f3205	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0290000000-a30ea02ff8d4d14ba7a4	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-0390000000-d4e36a90b7591787e67b	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-1390000000-b0af49def87c0211653c	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-0390000000-8b7f6cc8f51c032dd86d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00bd-4920000000-c1f07beecfc6ada179c1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9044000000-9dc0e361e3885451d81f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0790000000-a699ed429ebd1609f995	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03e9-0900000000-bbd302f8ff188f6cf93d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-053r-0900000000-6cc3ba396b1cfa8db1e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-053r-2900000000-90a465428eacaced71e2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0390000000-8d1a103c7fb1b7dfa685	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-25de1fda6182de338d15	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-053r-0900000000-e8cfeeeea0f83c87c0a3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0w29-0790000000-61308573c0d4d1caee8a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0w90-0590000000-9c6aa4b5a920add9f8ea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0930000000-074911d5bc17a486cbb0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0uk9-0190000000-9d6cad9671c04310ac0c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-05ox-2900000000-08b2a2c24032d96597db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000x-1900000000-9c83828dc6df75a0e798	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-001l-1900000000-dc720fc8e93906bb0c67	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014l-1970000000-6deb0cc19e89586090e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001l-0900000000-cab77201c86bda083dd0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-053r-1900000000-b1c220623de477b387ee	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-053r-0900000000-f7c54dfcc55add0c83d6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00b9-0950000000-e3f9fbda111b2109f630	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-b21f3fecc8ae15c125de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0900000000-817e4d468ea1bf1a3bc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2190000000-65b1ee730ae09a2cd6a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9650000000-68d73bfc7c9dd0f880e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9600000000-c58badf19c5cbb2f4347	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1950000000-5df9078df2a62ba2dc7e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Urine	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details

External Links

DrugBank ID

DB02959

HMDB ID

HMDB0000472

FooDB ID

FDB006231

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001371

BiGG ID

Not Available

BioCyc ID

5-HYDROXY-TRYPTOPHAN

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

M2MDB004850

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]

Showing metabocard for 5-Hydroxy-L-tryptophan (LMDB00161)

Structure for LMDB00161 (5-Hydroxy-L-tryptophan)