L-tryptophan (CHEBI:16828)

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CHEBI:16828 - L-tryptophan

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ChEBI Name	L-tryptophan

ChEBI ID	CHEBI:16828

ChEBI ASCII Name	L-tryptophan

Definition	The L-enantiomer of tryptophan.

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

Secondary ChEBI IDs	CHEBI:21407, CHEBI:45988, CHEBI:46125, CHEBI:46086, CHEBI:46225, CHEBI:184633, CHEBI:6310, CHEBI:13178

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

Download	Molfile XML SDF

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Molfile

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26 27 0 0 0 0 999 V2000

2.9290 0.1189 -1.3279 N 0 0 0 0 0 0 0 0 0 0 0 0

2.5404 0.2987 0.1097 C 0 0 2 0 0 0 0 0 0 0 0 0

3.5643 -0.3654 0.9937 C 0 0 0 0 0 0 0 0 0 0 0 0

4.5132 -0.9274 0.5018 O 0 0 0 0 0 0 0 0 0 0 0 0

1.1696 -0.3367 0.3508 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1300 0.3375 -0.5467 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.0087 1.8249 -0.1833 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.2420 -0.2469 -0.2960 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.4025 1.9886 0.2386 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.0743 0.7678 0.1580 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.7226 -1.5317 -0.4427 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.4046 0.4680 0.4602 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.0405 -1.8204 -0.1419 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.8788 -0.8173 0.3096 C 0 0 0 0 0 0 0 0 0 0 0 0

2.9800 1.2108 -1.4507 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1524 0.0677 -2.1053 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8780 -0.9731 -1.2051 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4939 1.3624 0.3432 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2161 -1.4004 0.1173 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8872 -0.2060 1.3954 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6661 2.0790 0.6341 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8000 2.8235 0.5317 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0666 -2.3140 -0.7950 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.0644 1.2467 0.8132 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.4147 -2.8266 -0.2594 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.9086 -1.0420 0.5452 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 15 1 0 0 0 0

1 16 1 0 0 0 0

1 17 1 0 0 0 0

2 3 1 0 0 0 0

4 3 2 0 0 0 0

5 2 1 0 0 0 0

6 5 1 0 0 0 0

6 7 1 0 0 0 0

6 8 1 0 0 0 0

9 7 1 0 0 0 0

9 10 1 0 0 0 0

9 22 1 0 0 0 0

10 8 4 0 0 0 0

11 8 4 0 0 0 0

12 10 4 0 0 0 0

12 14 4 0 0 0 0

13 11 4 0 0 0 0

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19 5 1 0 0 0 0

20 5 1 0 0 0 0

21 7 1 0 0 0 0

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24 12 1 0 0 0 0

25 13 1 0 0 0 0

26 14 1 0 0 0 0

M END): 17 ms

reading 26 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

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26 atoms created

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Molfile

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

C11H12N2O2

Net Charge

Average Mass

204.22526

Monoisotopic Mass

204.08988

InChI

InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1

InChIKey

QIVBCDIJIAJPQS-VIFPVBQESA-N

SMILES

N[C@@H](Cc1c[nH]c2ccccc12)C(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	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):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). micronutrient Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. (via tryptophan )

Application(s):	antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	L-tryptophan (CHEBI:16828) has role Escherichia coli metabolite (CHEBI:76971) L-tryptophan (CHEBI:16828) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) L-tryptophan (CHEBI:16828) has role antidepressant (CHEBI:35469) L-tryptophan (CHEBI:16828) has role human metabolite (CHEBI:77746) L-tryptophan (CHEBI:16828) has role micronutrient (CHEBI:27027) L-tryptophan (CHEBI:16828) has role mouse metabolite (CHEBI:75771) L-tryptophan (CHEBI:16828) has role nutraceutical (CHEBI:50733) L-tryptophan (CHEBI:16828) has role plant metabolite (CHEBI:76924) L-tryptophan (CHEBI:16828) is a L-α-amino acid (CHEBI:15705) L-tryptophan (CHEBI:16828) is a erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:73690) L-tryptophan (CHEBI:16828) is a proteinogenic amino acid (CHEBI:83813) L-tryptophan (CHEBI:16828) is a tryptophan (CHEBI:27897) L-tryptophan (CHEBI:16828) is conjugate acid of L-tryptophanate (CHEBI:32702) L-tryptophan (CHEBI:16828) is conjugate base of L-tryptophanium (CHEBI:32704) L-tryptophan (CHEBI:16828) is enantiomer of D-tryptophan (CHEBI:16296) L-tryptophan (CHEBI:16828) is tautomer of L-tryptophan zwitterion (CHEBI:57912)

Incoming	(2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate (CHEBI:140652) has functional parent L-tryptophan (CHEBI:16828) 5-methoxytryptophan (CHEBI:74049) has functional parent L-tryptophan (CHEBI:16828) L-tryptophan derivative (CHEBI:47994) has functional parent L-tryptophan (CHEBI:16828) L-tryptophanyl radical (CHEBI:32712) has functional parent L-tryptophan (CHEBI:16828) L-tryptophanyl radical cation (CHEBI:32713) has functional parent L-tryptophan (CHEBI:16828) Ala-Phe-Trp-Asn (CHEBI:73379) has functional parent L-tryptophan (CHEBI:16828) Ala-Trp-Asn-Asp (CHEBI:73382) has functional parent L-tryptophan (CHEBI:16828) Arg-Trp-Pro (CHEBI:156080) has functional parent L-tryptophan (CHEBI:16828) Arg-Trp-Ser-Tyr (CHEBI:73405) has functional parent L-tryptophan (CHEBI:16828) Asn-Met-Trp-Asn (CHEBI:73412) has functional parent L-tryptophan (CHEBI:16828) Asn-Trp (CHEBI:141425) has functional parent L-tryptophan (CHEBI:16828) Asn-Trp-Asp-Ser (CHEBI:73414) has functional parent L-tryptophan (CHEBI:16828) Asn-Trp-Cys-His (CHEBI:73415) has functional parent L-tryptophan (CHEBI:16828) Asp-Trp-Trp-Val (CHEBI:73440) has functional parent L-tryptophan (CHEBI:16828) cyclo-acetoacetyl-L-tryptophan(1−) (CHEBI:167552) has functional parent L-tryptophan (CHEBI:16828) Gln-Phe-Trp-Tyr (CHEBI:73464) has functional parent L-tryptophan (CHEBI:16828) Gln-Trp (CHEBI:141431) has functional parent L-tryptophan (CHEBI:16828) Glu-Ala-Trp (CHEBI:73490) has functional parent L-tryptophan (CHEBI:16828) Glu-Glu-Gln-Trp (CHEBI:73484) has functional parent L-tryptophan (CHEBI:16828) Glu-Gly-Trp (CHEBI:73496) has functional parent L-tryptophan (CHEBI:16828) Glu-Lys-Trp-Ala (CHEBI:73487) has functional parent L-tryptophan (CHEBI:16828) Glu-Trp (CHEBI:73512) has functional parent L-tryptophan (CHEBI:16828) Glu-Trp-Asp-Arg (CHEBI:138509) has functional parent L-tryptophan (CHEBI:16828) Ile-Leu-Trp-Trp (CHEBI:73518) has functional parent L-tryptophan (CHEBI:16828) Leu-Trp (CHEBI:73590) has functional parent L-tryptophan (CHEBI:16828) Lys-Ser-Trp (CHEBI:144474) has functional parent L-tryptophan (CHEBI:16828) Lys-Thr-Trp-Tyr (CHEBI:73597) has functional parent L-tryptophan (CHEBI:16828) notoamide (CHEBI:145690) has functional parent L-tryptophan (CHEBI:16828) Phe-Trp-Ala (CHEBI:73640) has functional parent L-tryptophan (CHEBI:16828) Phe-Trp-Trp (CHEBI:73642) has functional parent L-tryptophan (CHEBI:16828) Pro-Trp-Val-Gly (CHEBI:73650) has functional parent L-tryptophan (CHEBI:16828) proviolacein (CHEBI:131916) has functional parent L-tryptophan (CHEBI:16828) Ser-Trp (CHEBI:141445) has functional parent L-tryptophan (CHEBI:16828) Ser-Trp-Lys (CHEBI:144904) has functional parent L-tryptophan (CHEBI:16828) Thr-Trp (CHEBI:73666) has functional parent L-tryptophan (CHEBI:16828) Thr-Trp-Asp (CHEBI:73660) has functional parent L-tryptophan (CHEBI:16828) Trp-Ala (CHEBI:73710) has functional parent L-tryptophan (CHEBI:16828) Trp-Ala-Asp (CHEBI:73671) has functional parent L-tryptophan (CHEBI:16828) Trp-Ala-Gly (CHEBI:73691) has functional parent L-tryptophan (CHEBI:16828) Trp-Asn (CHEBI:141447) has functional parent L-tryptophan (CHEBI:16828) Trp-Asp-Ser (CHEBI:73692) has functional parent L-tryptophan (CHEBI:16828) Trp-Ile (CHEBI:141448) has functional parent L-tryptophan (CHEBI:16828) Trp-Pro (CHEBI:141449) has functional parent L-tryptophan (CHEBI:16828) Trp-Ser (CHEBI:73694) has functional parent L-tryptophan (CHEBI:16828) Trp-Thr (CHEBI:141450) has functional parent L-tryptophan (CHEBI:16828) Trp-Trp (CHEBI:74876) has functional parent L-tryptophan (CHEBI:16828) Trp-Trp-Val (CHEBI:144555) has functional parent L-tryptophan (CHEBI:16828) L-tryptophanium (CHEBI:32704) is conjugate acid of L-tryptophan (CHEBI:16828) L-tryptophanate (CHEBI:32702) is conjugate base of L-tryptophan (CHEBI:16828) D-tryptophan (CHEBI:16296) is enantiomer of L-tryptophan (CHEBI:16828) 1-L-tryptophano group (CHEBI:32710) is substituent group from L-tryptophan (CHEBI:16828) L-tryptophan residue (CHEBI:29954) is substituent group from L-tryptophan (CHEBI:16828) L-tryptophano group (CHEBI:32708) is substituent group from L-tryptophan (CHEBI:16828) L-tryptophyl group (CHEBI:32706) is substituent group from L-tryptophan (CHEBI:16828) L-tryptophan zwitterion (CHEBI:57912) is tautomer of L-tryptophan (CHEBI:16828)

IUPAC Name

L-tryptophan

INN	Source
tryptophan	KEGG DRUG

Synonyms	Sources
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid	IUPAC
(S)-α-amino-1H-indole-3-propanoic acid	NIST Chemistry WebBook
(S)-alpha-Amino-beta-(3-indolyl)-propionic acid	KEGG COMPOUND
(S)-tryptophan	NIST Chemistry WebBook
L-(−)-tryptophan	NIST Chemistry WebBook
L-β-3-indolylalanine	NIST Chemistry WebBook
L-Tryptophan	KEGG COMPOUND
L-tryptophan	ChEBI
Trp	ChEBI
Tryptophan	KEGG COMPOUND
TRYPTOPHAN	PDBeChem
W	ChEBI

Manual Xrefs	Databases
2780	DrugCentral
C00001396	KNApSAcK
C00078	KEGG COMPOUND
D00020	KEGG DRUG
DB00150	DrugBank
ECMDB00929	ECMDB
HMDB0000929	HMDB
TRP	PDBeChem
TRP	MetaCyc
Tryptophan	Wikipedia
YMDB00126	YMDB
View more database links

Registry Numbers	Types	Sources
51434	Gmelin Registry Number	Gmelin
73-22-3	CAS Registry Number	KEGG COMPOUND
73-22-3	CAS Registry Number	ChemIDplus
73-22-3	CAS Registry Number	NIST Chemistry WebBook
86197	Reaxys Registry Number	Reaxys

Citations	Types	Sources
11395471	PubMed citation	Europe PMC
11750787	PubMed citation	Europe PMC
11888576	PubMed citation	Europe PMC
12766158	PubMed citation	Europe PMC
12830226	PubMed citation	Europe PMC
12871129	PubMed citation	Europe PMC
15206750	PubMed citation	Europe PMC
16740930	PubMed citation	Europe PMC
16934873	PubMed citation	Europe PMC
17127472	PubMed citation	Europe PMC
17177562	PubMed citation	Europe PMC
17430113	PubMed citation	Europe PMC
17585690	PubMed citation	Europe PMC
17690425	PubMed citation	Europe PMC
17826001	PubMed citation	Europe PMC
18234569	PubMed citation	Europe PMC
18419734	PubMed citation	Europe PMC
18949702	PubMed citation	Europe PMC
19896323	PubMed citation	Europe PMC
21856896	PubMed citation	Europe PMC
22071091	PubMed citation	Europe PMC
22162421	PubMed citation	Europe PMC
22299628	PubMed citation	Europe PMC
22386992	PubMed citation	Europe PMC
22402312	PubMed citation	Europe PMC
22415302	PubMed citation	Europe PMC
22415306	PubMed citation	Europe PMC
2917974	PubMed citation	Europe PMC

Last Modified

26 January 2023

CHEBI:16828 - L-tryptophan

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