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CHEBI:16828 - L-tryptophan

ChEBI IDCHEBI:16828
ChEBI NameL-tryptophan
Stars
ASCII NameL-tryptophan
DefinitionThe L-enantiomer of tryptophan.
Secondary ChEBI IDsCHEBI:6310, CHEBI:13178, CHEBI:21407, CHEBI:45988, CHEBI:46086, CHEBI:46125, CHEBI:46225, CHEBI:184633
Last Modified17 June 2025
DownloadsMolfile
FormulaC11H12N2O2
Net Charge0
Average Mass204.229
Monoisotopic Mass204.08988
SMILESN[C@@H](Cc1cnc2ccccc12)C(=O)O
InChIInChI=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
InChIKeyQIVBCDIJIAJPQS-VIFPVBQESA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Saccharomyces cerevisiae (ncbitaxon:4932) - PubMed (24678285) Source: yeast.sf.net
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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.
micronutrient  Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
Saccharomyces cerevisiae metabolite  Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Daphnia magna metabolite  A Daphnia metabolite produced by the species Daphnia magna.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
(2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate (CHEBI:140652) 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)
5-methoxytryptophan (CHEBI:74049) 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)
cholyl-L-tryptophan (CHEBI:232263) 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)
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)
1-L-tryptophano group (CHEBI:32710) 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
tryptophanKEGG DRUG
Synonyms  Source
L-TryptophanKEGG COMPOUND
L-tryptophanChEBI
TrpChEBI
WChEBI
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acidIUPAC
TRYPTOPHANPDBeChem
Manual XrefsDatabases
C00078KEGG COMPOUND
TRPPDBeChem
D00020KEGG DRUG
DB00150DrugBank
HMDB0000929HMDB
TRPMetaCyc
TryptophanWikipedia
YMDB00126YMDB
ECMDB00929ECMDB
C00001396KNApSAcK
2780DrugCentral
Registry NumbersSources
Gmelin:51434Gmelin
Reaxys:86197Reaxys
CAS:73-22-3KEGG COMPOUND
CAS:73-22-3ChemIDplus
CAS:73-22-3NIST Chemistry WebBook
Citations