Showing Compound Card for d-Phenothrin (CDB006275)

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Record Information
Version1.0
Created at2020-07-28 20:24:20 UTC
Updated at2020-11-18 16:40:16 UTC
CannabisDB IDCDB006275
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Named-Phenothrin
Description(1R)-trans-phenothrin, also known as phenothrin or sumithrin, 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 (1R)-trans-phenothrin is possibly neutral.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
PhenothrinChEBI
SumithrinMeSH
Phenothrin, (trans-(+-))-isomerMeSH
Phenothrin, (1R-trans)-isomerMeSH
Phenothrin, (1S-trans)-isomerMeSH
(3-Phenoxyphenyl)methyl cis,trans-(+)-2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylateMeSH
Phenothrin, (1S-cis)-isomerMeSH
Phenothrin, (1R-cis)-isomerMeSH
D-PhenothrinMeSH
Phenothrin, (cis-(+-))-isomerMeSH
Chemical FormulaC23H26O3
Average Molecular Weight350.458
Monoisotopic Molecular Weight350.188194697
IUPAC Name(3-phenoxyphenyl)methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
Traditional Name(1R)-trans-phenothrin
CAS Registry NumberNot Available
SMILES
[H][C@@]1(C=C(C)C)[C@@]([H])(C(=O)OCC2=CC(OC3=CC=CC=C3)=CC=C2)C1(C)C
InChI Identifier
InChI=1S/C23H26O3/c1-16(2)13-20-21(23(20,3)4)22(24)25-15-17-9-8-12-19(14-17)26-18-10-6-5-7-11-18/h5-14,20-21H,15H2,1-4H3/t20-,21+/m1/s1
InChI KeySBNFWQZLDJGRLK-RTWAWAEBSA-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
  • Aromatic monoterpenoid
  • Benzyloxycarbonyl
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Phenoxy compound
  • Phenol ether
  • Monocyclic benzene moiety
  • Cyclopropanecarboxylic acid or derivatives
  • Benzenoid
  • Carboxylic acid ester
  • Ether
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen 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
logP6.42ALOGPS
logP5.57ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity103.84 m³·mol⁻¹ChemAxon
Polarizability39.82 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSd-Phenothrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-08-04View 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 ID82692
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91581
PDB IDNot Available
ChEBI ID39405
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 ]