ContaminantDB: Mesotrione

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2013-04-25 07:56:52 UTC

Update Date

2026-05-20 17:28:50 UTC

Accession Number

CHEM002837

Identification

Common Name

Mesotrione

Class

Small Molecule

Description

Mesotrione is an herbicide sold under the brand names Callisto and Tenacity. It is a synthetic analog of leptospermone developed to mimic the effects of this natural herbicide. Mesotrione works by inhibiting the plant enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD) which is necessary for carotenoid biosynthesis. Without the protection from carotenoids, the chlorophyll necessary for plant growth is degraded by sunlight.

Contaminant Sources

STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Ester
Ether
Herbicide
Ketone
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(2-Nitro-4-(methylsullfonyl))benzoylcyclohexane-1,3-dione	ChEBI
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
Tenacity	ChEBI
2-(2'-Nitro-4'-methylsulphonylbenzoyl)cyclohexane-1,3-dione	Generator
2-(4-Methylsulfonyl-2-nitrobenzoyl)-1,3-cyclohexanedione	Generator
2-[4-(Methylsulphonyl)-2-nitrobenzoyl]-1,3-cyclohexanedione	Generator
Callisto herbicide	MeSH
2-(4-Methanesulphonyl-2-nitrobenzoyl)cyclohexane-1,3-dione	Generator

Chemical Formula

C₁₄H₁₃NO₇S

Average Molecular Mass

339.321 g/mol

Monoisotopic Mass

339.041 g/mol

CAS Registry Number

104206-82-8

IUPAC Name

Not Available

Traditional Name

tenacity

SMILES

[H]C1=C([H])C(=C([H])C(=C1C(=O)C1([H])C(=O)C([H])([H])C([H])([H])C([H])([H])C1=O)[N+]([O-])=O)S(=O)(=O)C([H])([H])[H]

InChI Identifier

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

InChI Key

KPUREKXXPHOJQT-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzoylcyclohexane-1,3-diones. These are alkyl-phenylketones where the alkyl group is a cyclohexane 1,3-dione.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Benzoylcyclohexane-1,3-diones

Alternative Parents

Substituents

Benzoylcyclohexane-1,3-dione
Nitrobenzene
Benzenesulfonyl group
Aryl alkyl ketone
Nitroaromatic compound
Benzoyl
1,3-diketone
Monocyclic benzene moiety
Benzenoid
1,3-dicarbonyl compound
Sulfone
Sulfonyl
Organic nitro compound
Cyclic ketone
C-nitro compound
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organonitrogen compound
Organosulfur compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:38321 )
sulfone (CHEBI:38321 )
aromatic ketone (CHEBI:38321 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

herbicide

Biological Roles

EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor

Chemical Roles

EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.028 g/L	ALOGPS
logP	1.21	ALOGPS
logP	1.09	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	2.37	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	131.17 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.38 m³·mol⁻¹	ChemAxon
Polarizability	30.85 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9332000000-ed16e9c8ffe851a67705	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-0090000000-7c693e43e2c0e8b4281f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0006-0029000000-c726442c2de6a397ab47	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-004i-0090000000-6abcda78f920f8f65eaf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0006-0039000000-dec6a1c50fae31eb21ad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0ufr-4940000000-3a5a7c63820279541e78	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0ufr-6900000000-25b7278da99b9e910c8e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-0090000000-934210a1c4930140ddb2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0ufr-3940000000-74372decb9c16e1cdc72	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-004i-0190000000-5c122961997e43e29f0d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0006-0090000000-57310f73284941311f7c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0udi-3900000000-7a7a55ad34d2cb8e9c39	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-0090000000-779def23cef0544a1b74	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-004i-0090000000-95b8350e7546a4e44f4c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0006-0090000000-a157b0faa5a19bf7ff44	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-014i-0090000000-df5bec352c04c28bc43d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-0090000000-8e75ea2087c35e169bc0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0006-0090000000-45eb7a41dbd1146aebca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0090000000-e1f323a500027737e612	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0290000000-f0ee0946a9234315024f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-a37c4fd1699645904f34	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-1009000000-9d217fb6b489ac576b00	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9020000000-0a1e486fabb5500a8dea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-14db7c2cd0405b32a8d4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1009000000-2b04415b2a9791878feb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002o-9001000000-a52f055e7a150c901992	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Mesotrione

Chemspider ID

Not Available

ChEBI ID

38321

PubChem Compound ID

175967

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11455642

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20692682

Mesotrione (CHEM002837)

Structure for CHEM002837: Mesotrione