Topramezone (CHEM017438)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:20:51 UTC
Update Date2016-11-09 01:15:35 UTC
Accession NumberCHEM017438
Identification
Common NameTopramezone
ClassSmall Molecule
DescriptionAn aromatic ketone that is phenyl 1H-pyrazol-4-yl ketone in which the pyrazolyl group is substituted at positions 1 and 5 by methyl and hydroxy groups, respectively, and in which the phenyl group is substituted at positions 2, 3, and 4 by methyl, 4,5-dihydro-1,2-oxazol-3-yl, and methylsulfonyl groups, respectively. A potent inhibitor of 4-hydroxyphenylpyruvate dioxygenase (HPPD) that is rapily metabolised by corn to non-active substances, it is used as a herbicide for the treatment of broadleaf weeds.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
[3-(4,5-Dihydro-1,2-oxazol-3-yl)-4-(methanesulfonyl)-2-methylphenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanoneChEBI
[3-(4,5-Dihydro-1,2-oxazol-3-yl)-4-mesyl-O-tolyl](5-hydroxy-1-methylpyrazol-4-yl)methanoneChEBI
[3-(4,5-Dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanoneChEBI
ArmezonChEBI
BenzuocaotongChEBI
[3-(4,5-Dihydro-1,2-oxazol-3-yl)-4-(methanesulphonyl)-2-methylphenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanoneGenerator
[3-(4,5-Dihydro-3-isoxazolyl)-2-methyl-4-(methylsulphonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanoneGenerator
Chemical FormulaC16H17N3O5S
Average Molecular Mass363.390 g/mol
Monoisotopic Mass363.089 g/mol
CAS Registry Number210631-68-8
IUPAC Name4-[3-(4,5-dihydro-1,2-oxazol-3-yl)-4-methanesulfonyl-2-methylbenzoyl]-1-methyl-1H-pyrazol-5-ol
Traditional Name4-[3-(4,5-dihydro-1,2-oxazol-3-yl)-4-methanesulfonyl-2-methylbenzoyl]-2-methylpyrazol-3-ol
SMILESCN1N=CC(C(=O)C2=C(C)C(C3=NOCC3)=C(C=C2)S(C)(=O)=O)=C1O
InChI IdentifierInChI=1S/C16H17N3O5S/c1-9-10(15(20)11-8-17-19(2)16(11)21)4-5-13(25(3,22)23)14(9)12-6-7-24-18-12/h4-5,8,21H,6-7H2,1-3H3
InChI KeyIYMLUHWAJFXAQP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoylpyrazoles. These are aromatic compounds containing a benzoyl group substituted with a pyrazole ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoyl derivatives
Direct ParentBenzoylpyrazoles
Alternative Parents
Substituents
  • Benzoylpyrazole
  • Aryl-phenylketone
  • Benzenesulfonyl group
  • Aryl ketone
  • Toluene
  • Azole
  • Isoxazoline
  • Pyrazole
  • Sulfone
  • Sulfonyl
  • Vinylogous acid
  • Vinylogous amide
  • Heteroaromatic compound
  • Ketone
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.66 g/LALOGPS
logP1.13ALOGPS
logP1.32ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)2.52ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area110.85 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity102.66 m³·mol⁻¹ChemAxon
Polarizability35.98 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-20d954715c39b0196567Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1098000000-5410d7efcdd8708625a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9550000000-1e1cb86fbf1b25392173Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4029000000-e92ea7989ef947a4a81fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kdm-8029000000-b32cd54fd84e77898bb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-5e92f73fc708fae9c349Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID131999
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17340675
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21509485
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24086329
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26186714
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