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

13 14 4 0 0 0 0

18 2 1 0 0 0 0

19 5 1 0 0 0 0

20 5 1 0 0 0 0

21 7 1 0 0 0 0

23 11 1 0 0 0 0

24 12 1 0 0 0 0

25 13 1 0 0 0 0

26 14 1 0 0 0 0

M END): 18 ms

reading 26 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

26 atoms created

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

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Molfile

Wikipedia	License
Vitamin C (also known as ascorbic acid and ascorbate) is a water-soluble vitamin found in citrus and other fruits, berries and vegetables. It is also a generic prescription medication and in some countries is sold as a non-prescription dietary supplement. As a therapy, it is used to prevent and treat scurvy, a disease caused by vitamin C deficiency. Vitamin C is an essential nutrient involved in the repair of tissue, the formation of collagen, and the enzymatic production of certain neurotransmitters. It is required for the functioning of several enzymes and is important for immune system function. It also functions as an antioxidant. Vitamin C may be taken by mouth or by intramuscular, subcutaneous or intravenous injection. Various health claims exist on the basis that moderate vitamin C deficiency increases disease risk, such as for the common cold, cancer or COVID-19. There are also claims of benefits from vitamin C supplementation in excess of the recommended dietary intake for people who are not considered vitamin C deficient. Vitamin C is generally well tolerated. Large doses may cause gastrointestinal discomfort, headache, trouble sleeping, and flushing of the skin. The United States Institute of Medicine recommends against consuming large amounts.: 155–165 Most animals are able to synthesize their own vitamin C. However, apes (including humans) and monkeys (but not all primates), most bats, most fish, some rodents, and certain other animals must acquire it from dietary sources because a gene for a synthesis enzyme has mutations that render it dysfunctional. Vitamin C was discovered in 1912, isolated in 1928, and in 1933, was the first vitamin to be chemically produced. Partly for its discovery, Albert Szent-Györgyi was awarded the 1937 Nobel Prize in Physiology or Medicine.
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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