5-hydroxy-L-tryptophan (CHEBI:17780)

ChEBI > Main

CHEBI:17780 - 5-hydroxy-L-tryptophan

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	5-hydroxy-L-tryptophan

ChEBI ID	CHEBI:17780

ChEBI ASCII Name	5-hydroxy-L-tryptophan

Definition	The L-enantiomer of 5-hydroxytryptophan.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:12133, CHEBI:2064, CHEBI:20577

Supplier Information	We are unable to retrieve the vendor information for this entry at this time. Please try again later.

Download	Molfile XML SDF

more structures >>

call loadScript javascripts\jsmol\core\package.js

call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode

call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js

Jmol JavaScript applet jmolApplet0_object__897946430352584__ initializing

getValue debug = null

getValue logLevel = null

getValue allowjavascript = null

AppletRegistry.checkIn(jmolApplet0_object__897946430352584__)

call loadScript javascripts\jsmol\core\corestate.z.js

viewerOptions:

{ "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17780","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__897946430352584__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"897946430352584","bgcolor":"#000" }

Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $

java.vendor: j2s

java.version: 0.0

os.name: j2s

Access: ALL

memory: 0.0/0.0

processors available: 1

useCommandThread: false

appletId:jmolApplet0_object (signed)

starting HoverWatcher_1

getValue emulate = null

defaults = "Jmol"

getValue boxbgcolor = null

getValue bgcolor = #000

backgroundColor = "#000"

getValue ANIMFRAMECallback = null

getValue APPLETREADYCallback = Jmol._readyCallback

APPLETREADYCallback = "Jmol._readyCallback"

getValue ATOMMOVEDCallback = null

getValue CLICKCallback = null

getValue ECHOCallback = null

getValue ERRORCallback = null

getValue EVALCallback = null

getValue HOVERCallback = null

getValue LOADSTRUCTCallback = null

getValue MEASURECallback = null

getValue MESSAGECallback = null

getValue MINIMIZATIONCallback = null

getValue PICKCallback = null

getValue RESIZECallback = null

getValue SCRIPTCallback = null

getValue SYNCCallback = null

getValue STRUCTUREMODIFIEDCallback = null

getValue doTranslate = null

language=en_US

getValue popupMenu = null

getValue script = null

Jmol applet jmolApplet0_object__897946430352584__ ready

call loadScript javascripts\jsmol\core\corescript.z.js

call loadScript javascripts\jsmol\J\script\FileLoadThread.js

starting QueueThread0_2

script 1 started

starting HoverWatcher_3

starting HoverWatcher_4

The Resolver thinks Mol

4PQ - Ideal conformer

RDKit 3D

starting HoverWatcher_5

Time for openFile(4PQ - Ideal conformer

RDKit 3D

28 29 0 0 0 0 0 0 0 0999 V2000

1.4630 -1.1060 -1.0100 N 0 0 0 0 0 0 0 0 0 0 0 0

2.2110 0.0240 -0.4440 C 0 0 1 0 0 0 0 0 0 0 0 0

1.4880 0.5400 0.8020 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1480 1.1050 0.4080 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1310 2.3930 0.1490 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.4520 2.5280 -0.1760 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.0730 1.2970 -0.1330 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.3780 0.8770 -0.3710 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.7060 -0.4540 -0.2450 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.7420 -1.3910 0.1190 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.4410 -0.9940 0.3590 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.0960 0.3530 0.2290 C 0 0 0 0 0 0 0 0 0 0 0 0

3.5980 -0.4280 -0.0690 C 0 0 0 0 0 0 0 0 0 0 0 0

4.5800 0.4750 0.0850 O 0 0 0 0 0 0 0 0 0 0 0 0

3.8280 -1.6030 0.0930 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.0840 -2.7010 0.2450 O 0 0 0 0 0 0 0 0 0 0 0 0

1.8850 -1.4240 -1.8700 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3890 -1.8600 -0.3440 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2760 0.8230 -1.1830 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3440 -0.2810 1.5050 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0870 1.3200 1.2730 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5830 3.2020 0.1920 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8880 3.3640 -0.4030 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.1340 1.5950 -0.6540 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.7200 -0.7750 -0.4300 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6950 -1.7210 0.6420 H 0 0 0 0 0 0 0 0 0 0 0 0

5.4530 0.1370 0.3260 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.3800 -2.9470 1.1320 H 0 0 0 0 0 0 0 0 0 0 0 0

16 10 1 0

10 11 1 0

10 9 2 0

11 12 2 0

9 8 1 0

12 7 1 0

12 4 1 0

8 7 2 0

3 4 1 0

3 2 1 0

7 6 1 0

1 2 1 0

4 5 2 0

2 13 1 0

6 5 1 0

13 15 2 0

13 14 1 0

1 17 1 0

1 18 1 0

2 19 1 6

3 20 1 0

3 21 1 0

5 22 1 0

6 23 1 0

8 24 1 0

9 25 1 0

11 26 1 0

14 27 1 0

16 28 1 0

M END): 19 ms

reading 28 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

28 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
5-Hydroxytryptophan (5-HTP), used medically as oxitriptan, is a naturally occurring amino acid and chemical precursor as well as a metabolic intermediate in the biosynthesis of the neurotransmitter serotonin. 5-HTP can be manufactured and used as a drug and supplement with the INNTooltip International Nonproprietary Name oxitriptan. Brand names include Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum. As a drug, it is used in the treatment of depression and for certain other indications.
Read full article at Wikipedia

Formula

C11H12N2O3

Net Charge

Average Mass

220.228

Monoisotopic Mass

220.08479

InChI

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)/t9-/m0/s1

InChIKey

LDCYZAJDBXYCGN-VIFPVBQESA-N

SMILES

N[C@H](C(=O)O)CC=1C2=C(NC1)C=CC(=C2)O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via 5-hydroxytryptophan ) plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. neurotransmitter An endogenous compound that is used to transmit information across the synapse between a neuron and another cell. (via 5-hydroxytryptophan )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	5-hydroxy-L-tryptophan (CHEBI:17780) has role human metabolite (CHEBI:77746) 5-hydroxy-L-tryptophan (CHEBI:17780) has role mouse metabolite (CHEBI:75771) 5-hydroxy-L-tryptophan (CHEBI:17780) has role plant metabolite (CHEBI:76924) 5-hydroxy-L-tryptophan (CHEBI:17780) is a 5-hydroxytryptophan (CHEBI:28171) 5-hydroxy-L-tryptophan (CHEBI:17780) is a hydroxy-L-tryptophan (CHEBI:47995) 5-hydroxy-L-tryptophan (CHEBI:17780) is a non-proteinogenic L-α-amino acid (CHEBI:83822) 5-hydroxy-L-tryptophan (CHEBI:17780) is enantiomer of 5-hydroxy-D-tryptophan (CHEBI:43186) 5-hydroxy-L-tryptophan (CHEBI:17780) is tautomer of 5-hydroxy-L-tryptophan zwitterion (CHEBI:58266)

Incoming	5-hydroxy-D-tryptophan (CHEBI:43186) is enantiomer of 5-hydroxy-L-tryptophan (CHEBI:17780) 5-hydroxy-L-tryptophan zwitterion (CHEBI:58266) is tautomer of 5-hydroxy-L-tryptophan (CHEBI:17780)

IUPAC Names

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

5-hydroxy-L-tryptophan

Synonyms	Sources
5-hydroxy-L-tryptophan	ChEBI
5-Hydroxy-L-tryptophan	KEGG COMPOUND
5-hydroxytryptophan L-form	ChemIDplus
Cincofarm	ChemIDplus
L-5-hydroxytryptophan	ChemIDplus
Levothym	ChemIDplus
oxitriptan	ChemIDplus
Oxitriptan	KEGG COMPOUND
Tript-OH	ChemIDplus

Manual Xrefs	Databases
4006	DrugCentral
4PQ	PDBeChem
5-HYDROXY-TRYPTOPHAN	MetaCyc
5-Hydroxytryptophan	Wikipedia
C00001371	KNApSAcK
C00643	KEGG COMPOUND
D07339	KEGG DRUG
DB02959	DrugBank
HMDB0000472	HMDB
View more database links

Registry Numbers	Types	Sources
1862149	Gmelin Registry Number	Gmelin
4350-09-8	CAS Registry Number	ChemIDplus
88200	Reaxys Registry Number	Reaxys

Citations

Hara R, Kino K (2013)
Enhanced synthesis of 5-hydroxy-l-tryptophan through tetrahydropterin regeneration.
AMB Express 3, 70 [PubMed:24321061]
[show Abstract]

Matsuzaki H, Shimizu Y, Iwata N, Kamiuchi S, Suzuki F, Iizuka H, Hibino Y, Okazaki M (2013)
Antidepressant-like effects of a water-soluble extract from the culture medium of Ganoderma lucidum mycelia in rats.
BMC complementary and alternative medicine 13, 370 [PubMed:24369991]
[show Abstract]

Fox MA, Panessiti MG, Moya PR, Tolliver TJ, Chen K, Shih JC, Murphy DL (2013)
Mutations in monoamine oxidase (MAO) genes in mice lead to hypersensitivity to serotonin-enhancing drugs: implications for drug side effects in humans.
The pharmacogenomics journal 13, 551-557 [PubMed:22964922]
[show Abstract]

Iacono RP, Kuniyoshi SM, Ahlman JR, Zimmerman GJ, Maeda G, Pearlstein RD (1997)
Concentrations of indoleamine metabolic intermediates in the ventricular cerebrospinal fluid of advanced Parkinson's patients with severe postural instability and gait disorders.
Journal of neural transmission (Vienna, Austria : 1996) 104, 451-459 [PubMed:9295177]
[show Abstract]

Bell EA, Fellows LE (1966)
Occurrence of 5-hydroxy-L-tryptophan as a free plant amino-acid.
Nature 210, 529 [PubMed:5297581]

Last Modified

21 November 2019

ChEBI

CHEBI:17780 - 5-hydroxy-L-tryptophan

Background

Methods

Results

Conclusions

ChEBI is part of the ELIXIR infrastructure