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:CB4440420, eMolecules:505008, ZINC000000895466

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

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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

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M END): 27 ms

reading 26 atoms

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26 atoms created

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Wikipedia	License
Tryptophan (symbol Trp or W) is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromatic beta carbon substituent. Tryptophan is also a precursor to the neurotransmitter serotonin, the hormone melatonin, and vitamin B3 (niacin). It is encoded by the codon UGG. Like other amino acids, tryptophan is a zwitterion at physiological pH where the amino group is protonated (–NH+3; pKa = 9.39) and the carboxylic acid is deprotonated ( –COO−; pKa = 2.38). Humans and many animals cannot synthesize tryptophan: they need to obtain it through their diet, making it an essential amino acid. Tryptophan is named after the digestive enzymes trypsin, which were used in its first isolation from casein proteins. It was assigned the one-letter symbol W based on the double ring being visually suggestive to the bulky letter.
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

Last Modified

26 January 2023

CHEBI:16828 - L-tryptophan

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