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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:49:32 UTC
Update Date2022-03-07 02:56:32 UTC
HMDB IDHMDB0040292
Secondary Accession Numbers
  • HMDB40292
Metabolite Identification
Common NameImidacloprid
DescriptionImidacloprid is an insecticide Imidacloprid is a neonicotinoid, which is a class of neuro-active insecticides modeled after nicotine. Imidacloprid is a patented chemical, Imidacloprid is manufactured by Bayer Cropscience (part of Bayer AG) and sold under trade names Kohinor, Admire, Advantage, Gaucho, Merit, Confidor, Hachikusan, Premise, Prothor, and Winner. It is marketed as pest control, seed treatment, an insecticide spray, termite control, flea control, and a systemic insecticide.
Structure
Data?1563863519
Synonyms
ValueSource
1-((6-Chloro-3-pyridinyl)methyl)-N-nitro-2-imidazolidinimineChEBI
1-((6-Chloro-3-pyridyl)methyl)-N-nitro-2-imidazolidinimineChEBI
IMDChEBI
(e)-ImidaclopridHMDB
(Z)-ImidaclopridHMDB
1-(2-chloro-5-Pyridylmethyl)-2-(nitroimino)imidazolidineHMDB
1-[(6-chloro-3-Pyridinyl)methyl]-4,5-dihydro-N-nitro-1H-imidazol-2-amine, 9ciHMDB
AdmireHMDB
AdvantageHMDB
Advantage flea adulticideHMDB
Bayer brand OF imidaclopridHMDB
ConfidorHMDB
Confidor 200 SLHMDB
Confidor SLHMDB
GauchoHMDB
Imidacloprid (old RN)HMDB
MeritHMDB
Merit (insecticide)HMDB
Premise 75HMDB
ProvadoHMDB
Chemical FormulaC9H10ClN5O2
Average Molecular Weight255.66
Monoisotopic Molecular Weight255.0523023
IUPAC Name2-chloro-5-{[2-(nitroamino)-4,5-dihydro-1H-imidazol-1-yl]methyl}pyridine
Traditional Nameimidacloprid
CAS Registry Number105827-78-9
SMILES
[O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1
InChI Identifier
InChI=1S/C9H10ClN5O2/c10-8-2-1-7(5-12-8)6-14-4-3-11-9(14)13-15(16)17/h1-2,5H,3-4,6H2,(H,11,13)
InChI KeyYWTYJOPNNQFBPC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitroguanidines. These are organonitrogen compounds containing a nitro group, which is N-linked to a guanidine.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassGuanidines
Direct ParentNitroguanidines
Alternative Parents
Substituents
  • Nitroguanidine
  • 2-halopyridine
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • 2-imidazoline
  • Nitramine
  • Heteroaromatic compound
  • Organic nitro compound
  • Azacycle
  • Carboximidamide
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Organochloride
  • Organic oxygen compound
  • Organic zwitterion
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point143 - 144 °CNot Available
Boiling Point442.30 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility610 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP0.570The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP0.65ALOGPS
logP1.1ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.39ChemAxon
pKa (Strongest Basic)5.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area86.34 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity63.75 m³·mol⁻¹ChemAxon
Polarizability23.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+146.66230932474
DeepCCS[M-H]-144.26730932474
DeepCCS[M-2H]-177.78230932474
DeepCCS[M+Na]+152.57530932474
AllCCS[M+H]+153.832859911
AllCCS[M+H-H2O]+150.032859911
AllCCS[M+NH4]+157.332859911
AllCCS[M+Na]+158.432859911
AllCCS[M-H]-154.132859911
AllCCS[M+Na-2H]-154.132859911
AllCCS[M+HCOO]-154.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Imidacloprid[O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C13636.1Standard polar33892256
Imidacloprid[O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C12435.4Standard non polar33892256
Imidacloprid[O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C12565.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Imidacloprid,1TMS,isomer #1C[Si](C)(C)N1CCN(CC2=CC=C(Cl)N=C2)/C1=N/[N+](=O)[O-]2546.2Semi standard non polar33892256
Imidacloprid,1TMS,isomer #1C[Si](C)(C)N1CCN(CC2=CC=C(Cl)N=C2)/C1=N/[N+](=O)[O-]2274.9Standard non polar33892256
Imidacloprid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN(CC2=CC=C(Cl)N=C2)/C1=N/[N+](=O)[O-]2778.3Semi standard non polar33892256
Imidacloprid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN(CC2=CC=C(Cl)N=C2)/C1=N/[N+](=O)[O-]2492.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Imidacloprid GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2910000000-16207f958c3941d249012017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Imidacloprid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-qTof , Positive-QTOFsplash10-05di-2920000000-c29270e5a1a153c5bef72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-QTOF , negative-QTOFsplash10-0udi-0290000000-0812870c582a68d58f9e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-ITFT , negative-QTOFsplash10-0udi-0930000000-343db00f5be70f0fe78c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-ITFT , negative-QTOFsplash10-0udi-0090000000-719eaaca2c7a38c90d682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-ITFT , negative-QTOFsplash10-0udi-0090000000-942ea462298844bafdc22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-ITFT , negative-QTOFsplash10-0udi-0090000000-56328a93fd1e38aa22422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-ITFT , negative-QTOFsplash10-000i-9000000000-cad2f4a13e5493517e852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-ITFT , negative-QTOFsplash10-000i-9000000000-5f6d2d344bf6659eca472017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-ITFT , negative-QTOFsplash10-0udi-0090000000-68418a137b14a769367c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-ITFT , negative-QTOFsplash10-0udi-0090000000-47ad82be374a283a9dbb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-ITFT , negative-QTOFsplash10-0udi-0920000000-46ef972fc42dceee73932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-QFT , negative-QTOFsplash10-0udi-0090000000-fc3fa48055c83ff1de5f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0190000000-0cd6e54fe940f97ccb1d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-QTOF , positive-QTOFsplash10-056r-0980000000-e48625fbd18b2d626cc62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-QTOF , positive-QTOFsplash10-056r-0960000000-89d9de4658faefa962b12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-QTOF , positive-QTOFsplash10-0a6r-0940000000-16fe6279a6031f08bb672017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-QTOF , positive-QTOFsplash10-0aba-0910000000-2859fa22e79d10470b942017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-ITFT , positive-QTOFsplash10-08fr-0390000000-ab06f369da2af69be9242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidacloprid LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0190000000-af26c2abec118b42cc592017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidacloprid 10V, Positive-QTOFsplash10-0a4i-0090000000-3250c0b819f9c6714e582016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidacloprid 20V, Positive-QTOFsplash10-0a4j-0090000000-e8976c6ed0aab7cb6f362016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidacloprid 40V, Positive-QTOFsplash10-001l-7910000000-216222493c38e9ac9d302016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidacloprid 10V, Negative-QTOFsplash10-0udi-3090000000-b3146d60a6f2b5d2900c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidacloprid 20V, Negative-QTOFsplash10-0udi-2190000000-54519332ebe8fd4cbef02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidacloprid 40V, Negative-QTOFsplash10-0006-9100000000-b63d477ace752edc00a82016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11421
Phenol Explorer Compound IDNot Available
FooDB IDFDB020013
KNApSAcK IDNot Available
Chemspider ID77934
KEGG Compound IDC11110
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkImidacloprid
METLIN IDNot Available
PubChem Compound86418
PDB IDIM4
ChEBI ID5870
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1686991
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .