Prallethrin (CHEM003486)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (46)XML
Record Information
Version1.0
Creation Date2014-08-29 06:51:45 UTC
Update Date2026-03-31 17:21:41 UTC
Accession NumberCHEM003486
Identification
Common NamePrallethrin
ClassSmall Molecule
DescriptionPrallethrin is an exogenous organic compound with the formula C19H24O3 and an average molecular weight of 300.39 g/mol. At room temperature, it exists as a solid. Prallethrin belongs to the fatty acid esters, a subclass of fatty acyls within the organic compounds. As a pyrethroid insecticide, prallethrin is used in 1.6% w/w liquid vaporizers as a repellent for the control of mosquitoes in household settings. It also serves as the primary insecticide in certain products designed to kill hornets and wasps, as well as their nests. The compound acts on the nervous system of insects, utilizing a mode of action through contact to produce a rapid knock down effect. There are 19 recorded protein targets for this compound, including Retinoic acid receptor alpha (RARA), Peroxisome proliferator-activated receptor alpha (PPARA), Nuclear receptor subfamily 1 group I member 2 (NR1I2), Nuclear receptor subfamily 1 group I member 3 (NR1I3), and 15 other proteins.
Contaminant Sources
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Household Toxin
  • Insecticide
  • Organic Compound
  • Pesticide
  • Pyrethroid
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC19H24O3
Average Molecular Mass300.392 g/mol
Monoisotopic Mass300.173 g/mol
CAS Registry Number23031-36-9
IUPAC NameNot Available
Traditional Name(1R)-2-methyl-4-oxo-3-(prop-2-yn-1-yl)cyclopent-2-en-1-yl (1S,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
SMILES[H][C@]1(C=C(C)C)[C@]([H])(C(=O)O[C@]2([H])CC(=O)C(CC#C)=C2C)C1(C)C
InChI IdentifierInChI=1S/C19H24O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h1,9,14,16-17H,8,10H2,2-6H3/t14-,16+,17+/m0/s1
InChI KeySMKRKQBMYOFFMU-USXIJHARSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentPyrethroids
Alternative Parents
Substituents
  • Pyrethroid skeleton
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Cyclopropanecarboxylic acid or derivatives
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Acetylide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
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
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP3.56ALOGPS
logP3.55ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)18ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity87.13 m³·mol⁻¹ChemAxon
Polarizability34.23 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-0udi-1956000000-4d6dfef044e3b496261fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9840000000-1b4bcee717c957034794Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9400000000-d19946bcf4b5837f88e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0390000000-079c60b1b1ee3316ca09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-5960000000-24cdc4b4567adc861592Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00te-4900000000-9ae30e964188714c756fSpectrum
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/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 LinkPrallethrin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID16760153
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available