CHEBI:27897 - tryptophan

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ChEBI Name tryptophan
ChEBI ID CHEBI:27897
Definition An α-amino acid that is alanine bearing an indol-3-yl substituent at position 3.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:27163, CHEBI:9769
Supplier Information ChemicalBook:CB6107772, eMolecules:484485
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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)
InChIKey QIVBCDIJIAJPQS-UHFFFAOYSA-N
SMILES NC(Cc1c[nH]c2ccccc12)C(O)=O
Metabolite of Species Details
Daphnia magna (NCBI:txid35525) See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
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): Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing tryptophan (CHEBI:27897) has part 1H-indol-3-ylmethyl group (CHEBI:50337)
tryptophan (CHEBI:27897) has role Daphnia magna metabolite (CHEBI:83056)
tryptophan (CHEBI:27897) is a α-amino acid (CHEBI:33704)
tryptophan (CHEBI:27897) is a aminoalkylindole (CHEBI:38631)
tryptophan (CHEBI:27897) is a aromatic amino acid (CHEBI:33856)
tryptophan (CHEBI:27897) is a polar amino acid (CHEBI:26167)
tryptophan (CHEBI:27897) is conjugate acid of tryptophanate (CHEBI:32727)
tryptophan (CHEBI:27897) is conjugate base of tryptophanium (CHEBI:32728)
tryptophan (CHEBI:27897) is tautomer of tryptophan zwitterion (CHEBI:64554)
Incoming tryptophan derivative (CHEBI:27164) has functional parent tryptophan (CHEBI:27897)
tryptophanyl radical (CHEBI:32730) has functional parent tryptophan (CHEBI:27897)
tryptophanyl radical cation (CHEBI:32729) has functional parent tryptophan (CHEBI:27897)
D-tryptophan (CHEBI:16296) is a tryptophan (CHEBI:27897)
L-tryptophan (CHEBI:16828) is a tryptophan (CHEBI:27897)
tryptophanium (CHEBI:32728) is conjugate acid of tryptophan (CHEBI:27897)
tryptophanate (CHEBI:32727) is conjugate base of tryptophan (CHEBI:27897)
1-tryptophano group (CHEBI:32731) is substituent group from tryptophan (CHEBI:27897)
tryptophan residue (CHEBI:32732) is substituent group from tryptophan (CHEBI:27897)
tryptophano group (CHEBI:27165) is substituent group from tryptophan (CHEBI:27897)
tryptophyl group (CHEBI:37899) is substituent group from tryptophan (CHEBI:27897)
tryptophan zwitterion (CHEBI:64554) is tautomer of tryptophan (CHEBI:27897)
IUPAC Name
tryptophan
Synonyms Sources
2-amino-3-(1H-indol-3-yl)propanoic acid IUPAC
alpha-Amino-beta-(3-indolyl)-propionic acid KEGG COMPOUND
α-amino-β-3-indolepropionic acid ChEBI
β-3-indolylalanine ChEBI
Htrp IUPAC
triptófano ChEBI
Trp ChEBI
Tryptophan KEGG COMPOUND
tryptophane ChEBI
W ChEBI
Manual Xrefs Databases
C00001396 KNApSAcK
C00806 KEGG COMPOUND
LSM-36836 LINCS
Tryptophan Wikipedia
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Registry Numbers Types Sources
4532 Gmelin Registry Number Gmelin
54-12-6 CAS Registry Number NIST Chemistry WebBook
54-12-6 CAS Registry Number ChemIDplus
86196 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17439666 PubMed citation Europe PMC
22264337 PubMed citation Europe PMC
Last Modified
13 August 2019