Showing Compound Card for Cypermethrin (CDB006216)

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Record Information
Version1.0
Created at2020-07-28 20:16:20 UTC
Updated at2020-11-18 16:40:15 UTC
CannabisDB IDCDB006216
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCypermethrin
Description(1S,3S)-(R)-Cyano(3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, also known as zetagard or alpha-cypermethrin, 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. Based on a literature review a small amount of articles have been published on (1S,3S)-(R)-Cyano(3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
alpha-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateChEBI
ZetagardKegg
a-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateGenerator
a-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
alpha-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
Α-cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateGenerator
Α-cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
(1S,3S)-(R)-Cyano(3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
CymbushHMDB
alpha-CypermethrinHMDB
AlphacypermethrinHMDB
beta-CipermetrinaHMDB
SupercypermethrinHMDB
FastacHMDB
NRDC 149HMDB
Cypermethrin, (1R-(1alpha(r*),3beta))-isomerHMDB
Cypermethrin, (1R-(1alpha(s*),3beta))-isomerHMDB
FendonaHMDB
RipcordHMDB
SherpaHMDB
SupermethrinHMDB
Fastac 50EcHMDB
AlphamethrinHMDB
Cypermethrin, (1alpha(s*),3alpha)-(+-)-isomerHMDB
Chemical FormulaC22H19Cl2NO3
Average Molecular Weight416.297
Monoisotopic Molecular Weight415.074198893
IUPAC Namecyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Traditional Nameustaad
CAS Registry Number52315-07-8
SMILES
CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC(OC2=CC=CC=C2)=CC=C1
InChI Identifier
InChI=1S/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3
InChI KeyKAATUXNTWXVJKI-UHFFFAOYSA-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
  • Diphenylether
  • Diaryl ether
  • Benzyloxycarbonyl
  • Phenoxy compound
  • Phenol ether
  • Monocyclic benzene moiety
  • Cyclopropanecarboxylic acid or derivatives
  • Benzenoid
  • Carboxylic acid ester
  • Ketene acetal or derivatives
  • Carboxylic acid derivative
  • Ether
  • Chloroalkene
  • Monocarboxylic acid or derivatives
  • Carbonitrile
  • Nitrile
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point80.5°CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.0e-06 mg/mL at 20°C [WAUCHOPE,RD et al. (1991A)]Not Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.81ALOGPS
logP5.44ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)10.62ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.32 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity119.09 m³·mol⁻¹ChemAxon
Polarizability40.57 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-02cr-4910000000-8849f1db9e07694cee2f2014-09-20View Spectrum
Predicted GC-MSCypermethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCypermethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCypermethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCypermethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCypermethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0512900000-3c26550cde83f141de052016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-1912200000-b3b26bde64fbc63423e02016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052e-1900000000-a8aceee4a43e1d3139732016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0011900000-32f3cf0f9235364f299f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3346900000-98416964f4d22c0b70182016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9520000000-1bb5c04c6247a934fc532016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0038900000-53fc8b1c4fc4bcdfd2162021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0691-3391400000-39611d4b3cb6d43d0b1d2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-3890100000-3e4509fe741515b0ca5b2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0211900000-db6771eccb17edab98b42021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2860900000-dfb133d3ec704df3980f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9110000000-3657fc947a30f3439e8e2021-10-12View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0243566
DrugBank IDDB13721
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2809
KEGG Compound IDC10984
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCypermethrin
METLIN IDNot Available
PubChem Compound2912
PDB IDNot Available
ChEBI ID4042
References
General References
  1. Taylor A, Birkett JW: Pesticides in cannabis: A review of analytical and toxicological considerations. Drug Test Anal. 2020 Feb;12(2):180-190. doi: 10.1002/dta.2747. Epub 2020 Jan 19. [PubMed:31834671 ]