CHEBI:16946 - L-kynurenine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name L-kynurenine
ChEBI ID CHEBI:16946
ChEBI ASCII Name L-kynurenine
Definition A kynurenine that has L configuration.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:13129, CHEBI:43628, CHEBI:6258, CHEBI:21346
Supplier Information ChemicalBook:CB9679687, eMolecules:477205, ZINC000000000922
Download Molfile XML SDF
Wikipedia License
Aspirin () is the genericized trademark for acetylsalicylic acid (ASA), a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and inflammation, and as an antithrombotic. Specific inflammatory conditions that aspirin is used to treat include Kawasaki disease, pericarditis, and rheumatic fever. Aspirin is also used long-term to help prevent further heart attacks, ischaemic strokes, and blood clots in people at high risk. For pain or fever, effects typically begin within 30 minutes. Aspirin works similarly to other NSAIDs but also suppresses the normal functioning of platelets. One common adverse effect is an upset stomach. More significant side effects include stomach ulcers, stomach bleeding, and worsening asthma. Bleeding risk is greater among those who are older, drink alcohol, take other NSAIDs, or are on other blood thinners. Aspirin is not recommended in the last part of pregnancy. It is not generally recommended in children with infections because of the risk of Reye syndrome. High doses may result in ringing in the ears. A precursor to aspirin found in the bark of the willow tree (genus Salix) has been used for its health effects for at least 2,400 years. In 1853, chemist Charles Frédéric Gerhardt treated the medicine sodium salicylate with acetyl chloride to produce acetylsalicylic acid for the first time. Over the next 50 years, other chemists, mostly of the German company Bayer, established the chemical structure and devised more efficient production methods.: 69–75  Felix Hoffmann (or Arthur Eichengrün) of Bayer was the first to produce acetylsalicylic acid in a pure, stable form in 1897. By 1899, Bayer had dubbed this drug Aspirin and was selling it globally.: 27  Aspirin is available without medical prescription as a proprietary or generic medication in most jurisdictions. It is one of the most widely used medications globally, with an estimated 40,000 tonnes (44,000 tons) (50 to 120 billion pills) consumed each year, and is on the World Health Organization's List of Essential Medicines. In 2022, it was the 36th most commonly prescribed medication in the United States, with more than 16 million prescriptions.
Read full article at Wikipedia
Formula C10H12N2O3
Net Charge 0
Average Mass 208.21390
Monoisotopic Mass 208.08479
InChI InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1
InChIKey YGPSJZOEDVAXAB-QMMMGPOBSA-N
SMILES N[C@@H](CC(=O)c1ccccc1N)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
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): Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via kynurenine )
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing L-kynurenine (CHEBI:16946) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
L-kynurenine (CHEBI:16946) has role human metabolite (CHEBI:77746)
L-kynurenine (CHEBI:16946) has role mouse metabolite (CHEBI:75771)
L-kynurenine (CHEBI:16946) is a kynurenine (CHEBI:28683)
L-kynurenine (CHEBI:16946) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
L-kynurenine (CHEBI:16946) is conjugate acid of L-kynureninate (CHEBI:67010)
L-kynurenine (CHEBI:16946) is enantiomer of D-kynurenine (CHEBI:86262)
L-kynurenine (CHEBI:16946) is tautomer of L-kynurenine zwitterion (CHEBI:57959)
Incoming N-formyl-L-kynurenine (CHEBI:30249) has functional parent L-kynurenine (CHEBI:16946)
L-kynureninate (CHEBI:67010) is conjugate base of L-kynurenine (CHEBI:16946)
D-kynurenine (CHEBI:86262) is enantiomer of L-kynurenine (CHEBI:16946)
L-kynurenine zwitterion (CHEBI:57959) is tautomer of L-kynurenine (CHEBI:16946)
IUPAC Name
3-(2-aminobenzoyl)-L-alanine
Synonyms Sources
(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid IUPAC
3-Anthraniloyl-L-alanine KEGG COMPOUND
KYNURENINE PDBeChem
L-Kynurenine KEGG COMPOUND
Manual Xrefs Databases
C00007604 KNApSAcK
C00328 KEGG COMPOUND
CPD-14736 MetaCyc
DB02070 DrugBank
HMDB0000684 HMDB
KYN PDBeChem
Kynurenine Wikipedia
View more database links
Registry Numbers Types Sources
2922-83-0 CAS Registry Number KEGG COMPOUND
2922-83-0 CAS Registry Number ChemIDplus
2942333 Reaxys Registry Number Reaxys
Citation Type Source
22770225 PubMed citation Europe PMC
Last Modified
27 January 2016