Thiamethoxam (T3D3932)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2013-04-25 07:56:55 UTC
Update Date2014-12-24 20:26:34 UTC
Accession NumberT3D3932
Identification
Common NameThiamethoxam
ClassSmall Molecule
DescriptionThiamethoxam is a neonicotinoid insecticide, which is a class of neuro-active insecticides modeled after nicotine. Nicotine was identified and used as an insecticide and rat poison as early as the 1600’s. Its effectiveness as an insecticide spurred a search for insecticidal compounds that have selectively less effect on mammals, which led to the discovery of neonicotinoids. Neonicotinoids, like nicotine, bind to nicotinic acetylcholine receptors of a cell. In mammals, nicotinic acetylcholine receptors are located in cells of both the central and peripheral nervous systems. In insects these receptors are limited to the CNS. While low to moderate activation of these receptors causes nervous stimulation, high levels overstimulate and block the receptors causing paralysis and death. Nicotinic acetylcholine receptors are activated by the neurotransmitter acetylcholine. Acetylcholine is broken down by acetylcholinesterase to terminate signals from these receptors. However, acetylcholinesterase cannot break down neonicotinoids and the binding is irreversible. Because most neonicotinoids bind much more strongly to insect neuron receptors than to mammal neuron receptors, these insecticides are selectively more toxic to insects than mammals. The low mammalian toxicity of neonicotinoids can be explained in large part by their lack of a charged nitrogen atom at physiological pH. The uncharged molecule can penetrate the insect blood–brain barrier, while the mammalian blood–brain barrier filters it. However, Some neonicotinoid breakdown products are toxic to humans, especially if they have become charged. Because of their low toxicity and other favorable features, neonicotinoids are among the most widely used insecticides in the world. Most neonicotinoids are water-soluble and break down slowly in the environment, so they can be taken up by the plant and provide protection from insects as the plant grows. Neonicotinoids are currently used on corn, canola, cotton, sorghum, sugar beets and soybeans. They are also used on the vast majority of fruit and vegetable crops, including apples, cherries, peaches, oranges, berries, leafy greens, tomatoes, and potatoes. The use of neonicotinoids has been linked in a range of studies to adverse ecological effects, including honey-bee colony collapse disorder (CCD) and loss of birds due to a reduction in insect populations. This has led to moratoriums and bans on their use in Europe.
Compound Type
  • Amine
  • Ether
  • Insecticide
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
3-(2-Chloro-1,3-thiazol-5-ylmethyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene(nitro)amine
3-[(2-Chloro-1,3-thiazol-5-yl)methyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine
3-[(2-Chloro-5-thiazolyl)methyl]tetrahydro-5-methyl-N-nitro-4H-1,3,5-oxadiazin-4-imine
Actara
Adage
Cruiser
Diacloden
Chemical FormulaC8H10ClN5O3S
Average Molecular Mass291.715 g/mol
Monoisotopic Mass291.019 g/mol
CAS Registry Number153719-23-4
IUPAC Name(4Z)-3-[(2-chloro-1,3-thiazol-5-yl)methyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine
Traditional Namethiamethoxam
SMILESCN1COCN(CC2=CN=C(Cl)S2)\C1=N/[N+]([O-])=O
InChI IdentifierInChI=1S/C8H10ClN5O3S/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6/h2H,3-5H2,1H3/b11-8-
InChI KeyInChIKey=NWWZPOKUUAIXIW-FLIBITNWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2,5-disubstituted thiazoles. 2,5-disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 2 and 5 only.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassThiazoles
Direct Parent2,5-disubstituted thiazoles
Alternative Parents
Substituents
  • 2,5-disubstituted 1,3-thiazole
  • Aryl chloride
  • Aryl halide
  • Heteroaromatic compound
  • Guanidine
  • Organic nitro compound
  • Allyl-type 1,3-dipolar organic compound
  • Oxacycle
  • Azacycle
  • Organic 1,3-dipolar compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen 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 Point139.1°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP0.54ALOGPS
logP1.07ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)0.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area84.1 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.81 m³·mol⁻¹ChemAxon
Polarizability25.74 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 10V, positivesplash10-01ox-0090000000-b96956c5f01f7b4d87b82020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 20V, positivesplash10-001i-0930000000-c2368eb9e2ec01afe97d2020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 30V, positivesplash10-001i-0900000000-d8c26cd5c80e6ba674552020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 40V, positivesplash10-053r-0900000000-29bc8a1fa27dbbd0e44b2020-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-9352dc604b386f6ac9a12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-1090000000-3bb13ae0dfd8f9be65ec2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-6900000000-1b53cccfd2735db5c0df2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3090000000-958ae188a575a58163bc2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9100000000-5621eb62e7c5584c2a8a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-6c00dbb61be83b615c662016-08-03View 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 ID5485188
ChEMBL IDCHEMBL1896251
ChemSpider ID4588645
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
MSDST3D3932.pdf
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Urokinase plasminogen activator surface receptor
General Function:
Urokinase plasminogen activator receptor activity
Specific Function:
Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
Gene Name:
PLAUR
Uniprot ID:
Q03405
Molecular Weight:
36977.62 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.48 uMBSK_BE3C_uPAR_upBioSeek
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
2. Cytochrome P450 3A4
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.18 uMCLZD_CYP3A4_48CellzDirect
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]