Mesosulfuron-methyl (T3D3875)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2013-04-25 07:56:52 UTC
Update Date2014-12-24 20:26:33 UTC
Accession NumberT3D3875
Identification
Common NameMesosulfuron-methyl
ClassSmall Molecule
DescriptionMetsulfuron-methyl is a residual sulfonylurea herbicide that kills broadleaf weeds and some annual grasses. It is a systemic compound with foliar and soil activity, that inhibits cell division in shoots and roots. It has very low toxicity to mammals, birds, fish, and insects, but is a moderate eye irritant.
Compound Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Herbicide
  • Lachrymator
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
Methyl 2-({[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]amino}sulfonyl)-4-{[(methylsulfonyl)amino]methyl}benzoate
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-4-[[(methylsulfonyl)amino]methyl]benzoate
Methyl 2-{[(4,6-dimethoxy-2-pyrimidinyl)carbamoyl]sulfamoyl}-4-{[(methylsulfonyl)amino]methyl}benzoate
Methyl 2-{[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]sulfamoyl}-4-{[(methylsulfonyl)amino]methyl}benzoate
Chemical FormulaC17H21N5O9S2
Average Molecular Mass503.507 g/mol
Monoisotopic Mass503.078 g/mol
CAS Registry Number208465-21-8
IUPAC Namemethyl 2-({[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]amino}sulfonyl)-4-(methanesulfonamidomethyl)benzoate
Traditional Namemethyl 2-{[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]aminosulfonyl}-4-(methanesulfonamidomethyl)benzoate
SMILESCOC(=O)C1=C(C=C(CNS(C)(=O)=O)C=C1)S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1
InChI IdentifierInChI=1S/C17H21N5O9S2/c1-29-13-8-14(30-2)20-16(19-13)21-17(24)22-33(27,28)12-7-10(9-18-32(4,25)26)5-6-11(12)15(23)31-3/h5-8,18H,9H2,1-4H3,(H2,19,20,21,22,24)
InChI KeyInChIKey=NIFKBBMCXCMCAO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidinyl-2-sulfonylureas. These are aromatic heterocyclic compounds containing a pyrimidine ring which is substituted with a sulfonylurea at the ring 2-position.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassSulfonylureas
Direct ParentPyrimidinyl-2-sulfonylureas
Alternative Parents
Substituents
  • Pyrimidinyl-2-sulfonylurea
  • Benzenesulfonamide
  • Benzoate ester
  • Benzenesulfonyl group
  • Benzoic acid or derivatives
  • Benzoyl
  • Alkyl aryl ether
  • Pyrimidine
  • Organic sulfonic acid amide
  • Organosulfonic acid amide
  • Benzenoid
  • Monocyclic benzene moiety
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Methyl ester
  • Organic sulfonic acid or derivatives
  • Heteroaromatic compound
  • Carbonic acid derivative
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organosulfur compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
logP0.55ALOGPS
logP0.55ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)1.68ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area191.98 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity116.62 m³·mol⁻¹ChemAxon
Polarizability47.97 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0239880000-075269fdb460cee12bdb2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-1795100000-3a17fa51e80c10e013e92016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-1973000000-8013ea23af21fd43ecc02016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-4904580000-0321a16ea35ff9ecafdb2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pk9-9034100000-f773442f13263d5074b02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9220000000-9e06cc687d570f1d7e8f2016-08-03View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID11409499
ChEMBL IDCHEMBL1883630
ChemSpider ID9584394
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3875.pdf
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]