Clothianidin (CHEM002776)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (8)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:50 UTC
Update Date2016-11-09 01:08:58 UTC
Accession NumberCHEM002776
Identification
Common NameClothianidin
ClassSmall Molecule
DescriptionClothianidin 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.
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Insecticide
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(e)-N-(2-Chloro-5-thiazolyl)methyl-n'-methyl-n''-nitroguanidineChEBI
((e)-1-(2-chloro-1,3-Thiazol-5-ylmethyl)-3-methyl-2-nitroguanidine)MeSH
Chemical FormulaC6H8ClN5O2S
Average Molecular Mass249.678 g/mol
Monoisotopic Mass249.009 g/mol
CAS Registry Number210880-92-5
IUPAC Name(E)-N'-[(2-chloro-1,3-thiazol-5-yl)methyl]-N-methyl-N''-nitroguanidine
Traditional Namecelero
SMILESCN\C(NCC1=CN=C(Cl)S1)=N/[N+]([O-])=O
InChI IdentifierInChI=1S/C6H8ClN5O2S/c1-8-6(11-12(13)14)10-3-4-2-9-5(7)15-4/h2H,3H2,1H3,(H2,8,10,11)
InChI KeyPGOOBECODWQEAB-UHFFFAOYSA-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
  • Nitroguanidine
  • Aryl chloride
  • Aryl halide
  • Nitramine
  • Heteroaromatic compound
  • Guanidine
  • Organic nitro compound
  • Carboximidamide
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Imine
  • Organic zwitterion
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP0.62ALOGPS
logP0.54ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)0.41ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity55.53 m³·mol⁻¹ChemAxon
Polarizability22.17 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 17V, positivesplash10-014i-0910000000-6385f1a3a7f91ed7e982Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 7V, positivesplash10-0gc0-0950000000-d29e3319f44939e2ffe7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 14V, positivesplash10-0159-0900000000-653b260bb023add99e31Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 22V, positivesplash10-00lr-0900000000-b5f88b04d76924d17378Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 29V, positivesplash10-01q9-0900000000-ed2f06c069aed87e9f9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 37V, positivesplash10-03e9-0900000000-f9169babd128a490c689Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 44V, positivesplash10-03e9-2900000000-84040d7ff64bca37fde8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 17V, positivesplash10-0159-0900000000-97745f6dc45dd1581765Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 10V, positivesplash10-014i-0920000000-fec4e86ce184bd252665Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 20V, positivesplash10-02u0-0900000000-c422082c73e9f46c2713Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 30V, positivesplash10-03e9-0900000000-d266e4d6dacfa337ada0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 40V, positivesplash10-03di-0900000000-019d795fba7ac99240cfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-0gb9-0940000000-d3f42327bbe9eaebd932Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-0159-0900000000-b753f5e40fab4c8f7092Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-00lr-0900000000-c9321c59320cacc256daSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-001i-0900000000-11d29a227bda097d127cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-001i-0900000000-7e088dfb25fbf5322caeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 24V, positivesplash10-0159-0900000000-66c374cc807fdd5fc988Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 17V, negativesplash10-02t9-0910000000-6ad88fdea0ea1ddc8781Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-cf623673de668657f311Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-0190000000-392883a85c2c2015b0c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-044i-9500000000-499b35d8d5d2f169387dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-4090000000-770d5ba68ba065242bf7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2190000000-82b6362d6ef9385de1d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bti-9200000000-2b339e51e2cf38532f75Spectrum
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
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 LinkClothianidin
Chemspider IDNot Available
ChEBI ID39177
PubChem Compound ID213027
Kegg Compound IDC18508
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available