Showing Compound Card for Resmethrin (CDB006297)

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Record Information
Version1.0
Created at2020-07-28 20:25:44 UTC
Updated at2020-11-18 16:40:17 UTC
CannabisDB IDCDB006297
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameResmethrin
DescriptionResmethrin, also known as durekyl or ectokyl, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review a significant number of articles have been published on Resmethrin.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5-(Phenylmethyl)-3-furanyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylateChEBI
5-Benzyl-3-furylmethyl (+-)-cis,trans-chrysanthemateChEBI
5-Benzyl-3-furylmethyl (1Rs,3Rs;1Rs,3Sr)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylateChEBI
DurekylKegg
EctokylKegg
(5-(Phenylmethyl)-3-furanyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acidGenerator
5-Benzyl-3-furylmethyl (+-)-cis,trans-chrysanthemic acidGenerator
5-Benzyl-3-furylmethyl (1Rs,3Rs;1Rs,3Sr)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acidGenerator
(5-Benzyl-3-furyl)methyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropemecarboxylateMeSH
ScourgeMeSH
Chemical FormulaC22H26O3
Average Molecular Weight338.44
Monoisotopic Molecular Weight338.188194698
IUPAC Name(5-benzylfuran-3-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
Traditional Namefor-syn
CAS Registry Number10453-86-8
SMILES
CC(C)=CC1C(C(=O)OCC2=COC(CC3=CC=CC=C3)=C2)C1(C)C
InChI Identifier
InChI=1S/C22H26O3/c1-15(2)10-19-20(22(19,3)4)21(23)25-14-17-12-18(24-13-17)11-16-8-6-5-7-9-16/h5-10,12-13,19-20H,11,14H2,1-4H3
InChI KeyVEMKTZHHVJILDY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Monocyclic benzene moiety
  • Cyclopropanecarboxylic acid or derivatives
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point56.5°CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.8e-05 mg/mL at 25°C [TOMLIN,C (1997)]Not Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.38ALOGPS
logP5.07ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.44 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity99.88 m³·mol⁻¹ChemAxon
Polarizability38.34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00dl-8900000000-c40ec51d53be4cbfb9d12014-09-20View Spectrum
Predicted GC-MSResmethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSResmethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00dl-2920000000-df032c0bc12bc76557a12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0079-0429000000-10dc84a36c0b4b3c249f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0006-4900000000-bf183a6a22511c91d0522021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0006-6900000000-5674fd24cdad4874ee162021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00dl-2920000000-755626dfa3e8e43acd4f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-002f-8900000000-884e993eff83a90f18db2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-002f-9700000000-e1997e6b5a9d9260999a2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0926000000-0fb918a4bbc4bee251b82016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1911000000-a86170594036d2641bee2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l6r-4900000000-18c056037d5a7b1ebb5e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0409000000-d88ffbc582501a3192352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bj-0912000000-763c41ab2e9c3ea0e3ec2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00rt-1900000000-16d53356f64b1d6c2c342016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100.40 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0257162
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4877
KEGG Compound IDC10991
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkResmethrin
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID8811
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 ]