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:CB3349447, ChemicalBook:CB6349448, eMolecules:495715, ZINC000003078958
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Atrazine ( A-trə-zeen) is a chlorinated herbicide of the triazine class. It is used to prevent pre-emergence broadleaf weeds in crops such as maize (corn), soybean and sugarcane and on turf, such as golf courses and residential lawns. Atrazine's primary manufacturer is Syngenta and it is one of the most widely used herbicides in the United States, Canadian, and Australian agriculture. Its use was banned in the European Union in 2004, when the EU found groundwater levels exceeding the limits set by regulators, and Syngenta could not show that this could be prevented nor that these levels were safe. At least two significant Canadian farm well studies showed that atrazine was the most common contaminant found. As of 2001, atrazine was the most commonly detected pesticide contaminating drinking water in the U.S.: 44  Studies suggest it is an endocrine disruptor, an agent that can alter the natural hormonal system. However, in 2006 the U.S. Environmental Protection Agency (EPA) had stated that under the Food Quality Protection Act "the risks associated with the pesticide residues pose a reasonable certainty of no harm", and in 2007, the EPA said that atrazine does not adversely affect amphibian sexual development and that no additional testing was warranted. The EPA's 2009 review concluded that "the agency's scientific bases for its regulation of atrazine are robust and ensure prevention of exposure levels that could lead to reproductive effects in humans". However, in their 2016 Refined Ecological Risk Assessment for Atrazine, it was stated that "it is difficult to make definitive conclusions about the impact of atrazine at a given concentration but multiple studies have reported effects to various endpoints at environmentally-relevant concentrations." EPA started a registration review in 2013. The EPA's review has been criticized, and the safety of atrazine remains controversial. EPA has however stated that "If at any time EPA determines there are urgent human or environmental risks from atrazine exposure that require prompt attention, we will take appropriate regulatory action, regardless of the status of the registration review process."
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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