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InChI=1S/CH4O/c1-2/h2H,1H3
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ChEBI
> Main
CHEBI:16828 -
L
-tryptophan
Main
ChEBI Ontology
Automatic Xrefs
Reactions
Pathways
Models
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
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Wikipedia
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Read full article at Wikipedia
Formula
C11H12N2O2
Net Charge
0
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 (Br
o
nsted acid).
(via
organic amino compound
)
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Br
o
nsted 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
(2
S
)-3-(1
H
-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
(2
S
)-2-amino-3-(1
H
-indol-3-yl)propanoic acid
IUPAC
(
S
)-α-amino-1
H
-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
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PubMed citation
Europe PMC
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PubMed citation
Europe PMC
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PubMed citation
Europe PMC
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PubMed citation
Europe PMC
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PubMed citation
Europe PMC
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PubMed citation
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PubMed citation
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PubMed citation
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PubMed citation
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PubMed citation
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PubMed citation
Europe PMC
22071091
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Europe PMC
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Europe PMC
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Last Modified
26 January 2023