CHEBI:38321 - mesotrione

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ChEBI Name mesotrione
ChEBI ID CHEBI:38321
Definition An aromatic ketone that is cyclohexa-1,3-dione in which one of the hydrogens at position 2 is substituted by a 4-(methanesulfonyl)-2-nitrobenzoyl group.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C14H13NO7S
Net Charge 0
Average Mass 339.32156
Monoisotopic Mass 339.041
InChI InChI=1S/C14H13NO7S/c1-23(21,22)8-5-6-9(10(7-8)15(19)20)14(18)13-11(16)3-2-4-12(13)17/h5-7,13H,2-4H2,1H3
InChIKey KPUREKXXPHOJQT-UHFFFAOYSA-N
SMILES CS(=O)(=O)c1ccc(C(=O)C2C(=O)CCCC2=O)c(c1)[N+]([O-])=O
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): carotenoid biosynthesis inhibitor
Any pathway inhibitor that acts on the carotenoid biosynthesis pathway.
EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor
An EC 1.13.11.* (oxidoreductase acting on single donors and incorporating 2 atoms of oxygen) inhibitor that interferes with the activity of 4-hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27).
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): herbicide
A substance used to destroy plant pests.
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ChEBI Ontology
Outgoing mesotrione (CHEBI:38321) has functional parent benzophenone (CHEBI:41308)
mesotrione (CHEBI:38321) has role carotenoid biosynthesis inhibitor (CHEBI:138208)
mesotrione (CHEBI:38321) has role EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor (CHEBI:38317)
mesotrione (CHEBI:38321) has role environmental contaminant (CHEBI:78298)
mesotrione (CHEBI:38321) has role herbicide (CHEBI:24527)
mesotrione (CHEBI:38321) has role xenobiotic (CHEBI:35703)
mesotrione (CHEBI:38321) is a β-triketone (CHEBI:140323)
mesotrione (CHEBI:38321) is a C-nitro compound (CHEBI:35716)
mesotrione (CHEBI:38321) is a aromatic ketone (CHEBI:76224)
mesotrione (CHEBI:38321) is a sulfone (CHEBI:35850)
Incoming nitisinone (CHEBI:50378) is a mesotrione (CHEBI:38321)
IUPAC Name
2-[4-(methanesulfonyl)-2-nitrobenzoyl]cyclohexane-1,3-dione
Synonyms Sources
(2-nitro-4-(methylsullfonyl))benzoylcyclohexane-1,3-dione ChemIDplus
2-(2'-nitro-4'-methylsulfonylbenzoyl)cyclohexane-1,3-dione ChEBI
2-(4-methylsulphonyl-2-nitrobenzoyl)-1,3-cyclohexanedione ChEBI
2-[4-(methylsulfonyl)-2-nitrobenzoyl]-1,3-cyclohexanedione ChEBI
Brand Name Source
Tenacity ChEBI
Manual Xrefs Databases
442 PPDB
mesotrione Alan Wood's Pesticides
Mesotrione Wikipedia
WO2011016018 Patent
View more database links
Registry Numbers Types Sources
104206-82-8 CAS Registry Number ChemIDplus
8999656 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11455642 PubMed citation Europe PMC
20692682 PubMed citation Europe PMC
Last Modified
04 March 2018
General Comments
2011-07-18 Mesotrione is an inhibitor of 4-hydroxyphenylpyruvate dioxygenase (HPPD). It is used as a herbicide for contol of broadleaf weeds. Following treatment to sensitive plants, carotenoid biosynthesis is disrupted in the chlorophyll pathway, resulting in a bleaching effect.
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag