Showing Compound Card for cis-Permethrin (CDB006289)

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Record Information
Version1.0
Created at2020-07-28 20:25:11 UTC
Updated at2020-11-18 16:40:17 UTC
CannabisDB IDCDB006289
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namecis-Permethrin
DescriptionCIS-PERMETHRIN, also known as cis permethrin or ambush, 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. CIS-PERMETHRIN is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Permethrin, (cis-(+-))-isomerMeSH
Permethrin, (1R-trans)-isomerMeSH
Permethrin, (1S-cis)-isomerMeSH
Permethrin, (cis)-isomerMeSH
cis PermethrinMeSH
AmbushMeSH
NRDC 147MeSH
ElimiteMeSH
trans PermethrinMeSH
3-Phenoxybenzyl-cis,trans-(1Rs)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateMeSH
NRDC-143MeSH
NRDC-147MeSH
Permethrin, (1S-trans)-isomerMeSH
(m-Phenoxybenzyl)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateMeSH
Permethrin, (trans)-isomerMeSH
NRDC 143MeSH
cis-(1Rs)-PermethrinMeSH
NittiforMeSH
Permethrin, trans-(1Rs)-isomerMeSH
PermethrinMeSH
Permethrin, (trans-(+-))-isomerMeSH
trans-PermethrinMeSH
NRDC147MeSH
Permethrin, cis-(1Rs)-isomerMeSH
3-Phenoxybenzyl-(+-)-cis,trans-2,2-dichlorovinyl-2,2-dimethyl-cyclopropylcarboxylic acid, esterMeSH
NRDC143MeSH
Permethrin, (1R-cis)-isomerMeSH
trans-(1Rs)-PermethrinMeSH
(RR)-trans-PermethrinChEMBL
(3-Phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acidGenerator
cis-PermethrinMeSH
Chemical FormulaC21H20Cl2O3
Average Molecular Weight391.29
Monoisotopic Molecular Weight390.0789499
IUPAC Name(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Traditional Nameacticin
CAS Registry NumberNot Available
SMILES
[H][C@]1(C=C(Cl)Cl)[C@@]([H])(C(=O)OCC2=CC(OC3=CC=CC=C3)=CC=C2)C1(C)C
InChI Identifier
InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3/t17-,19-/m0/s1
InChI KeyRLLPVAHGXHCWKJ-HKUYNNGSSA-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
  • Chloroalkene
  • Haloalkene
  • Ether
  • Vinyl halide
  • Monocarboxylic acid or derivatives
  • Vinyl chloride
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.24ALOGPS
logP5.7ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity114.28 m³·mol⁻¹ChemAxon
Polarizability39.21 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MScis-Permethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0519000000-0f6eb9a687fe3c0d66c42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1923000000-a400c6833ac566d7a6222016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052e-2900000000-7758be41aece58f5d5d12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0109000000-fdac422c546f05b83ceb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1709000000-f755eb7d0bee859d0bb82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-97e9860533a91746241d2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound40463
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Moulins JR, Blais M, Montsion K, Tully J, Mohan W, Gagnon M, McRitchie T, Kwong K, Snider N, Blais DR: Multiresidue Method of Analysis of Pesticides in Medical Cannabis. J AOAC Int. 2018 Nov 1;101(6):1948-1960. doi: 10.5740/jaoacint.17-0495. Epub 2018 May 29. [PubMed:29843862 ]