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

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CHEBI:17780 - 5-hydroxy-L-tryptophan

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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	ChemicalBook:CB7853704, ChemicalBook:CB3777943, eMolecules:26405050, eMolecules:29534153, eMolecules:492402, Selleckchem:vitamin-c-ascorbic-acid, ZINC000100006770

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

4PQ - Ideal conformer

RDKit 3D

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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

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1 17 1 0

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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): 18 ms

reading 28 atoms

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Wikipedia	License
Triiodothyronine, also known as T3, is a thyroid hormone. It affects almost every physiological process in the body, including growth and development, metabolism, body temperature, and heart rate. Production of T3 and its prohormone thyroxine (T4) is activated by thyroid-stimulating hormone (TSH), which is released from the anterior pituitary gland. This pathway is part of a closed-loop feedback process: Elevated concentrations of T3, and T4 in the blood plasma inhibit the production of TSH in the anterior pituitary gland. As concentrations of these hormones decrease, the anterior pituitary gland increases production of TSH, and by these processes, a feedback control system stabilizes the level of thyroid hormones in the bloodstream. At the cellular level, T3 is the body's more active and potent thyroid hormone. T3 helps deliver oxygen and energy to all of the body's cells, its effects on target tissues being roughly four times more potent than those of T4. Of the thyroid hormone that is produced, just about 20% is T3, whereas 80% is produced as T4. Roughly 85% of the circulating T3 is later formed in the liver and anterior pituitary by removal of the iodine atom from the carbon atom number five of the outer ring of T4. In any case, the concentration of T3 in the human blood plasma is about one-fortieth that of T4. The half-life of T3 is about 2.5 days. The half-life of T4 is about 6.5 days. T3 levels start to rise 45 minutes after administration and peak at about 2.5 hours. Although manufacturer of Cytomel states half-life to be 2.5 days the half-life variability is great and can vary depending on the thyroid status of the patient. Newer studies have found the pharmakokinetics of T3 to be complex and the half-life to vary between 10 – 22 hours.
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	Types	Sources
22964922	PubMed citation	Europe PMC
24321061	PubMed citation	Europe PMC
24369991	PubMed citation	Europe PMC
5297581	PubMed citation	Europe PMC
9295177	PubMed citation	Europe PMC

Last Modified

21 November 2019

CHEBI:17780 - 5-hydroxy-L-tryptophan

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