Showing Compound Card for Pyrethrins I (CDB006299)

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Record Information
Version1.0
Created at2020-07-28 20:25:51 UTC
Updated at2020-11-18 16:40:17 UTC
CannabisDB IDCDB006299
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePyrethrins I
Descriptionpyrethrin I, also known as bubil, belongs to the class of organic compounds known as pyrethrins. These are pyrethroids with a structure based on a skeleton that is characterized by the presence of a chrysanthemic acid esterified with a cyclopentenone derivative. pyrethrin I is possibly neutral.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Chrysanthemum monocarboxylic acid pyrethrolone esterChEBI
BubilKegg
Chrysanthemum monocarboxylate pyrethrolone esterGenerator
Pyrethrin IIMeSH
Chemical FormulaC21H28O3
Average Molecular Weight328.452
Monoisotopic Molecular Weight328.203844762
IUPAC Name(1S)-2-methyl-4-oxo-3-[(2Z)-penta-2,4-dien-1-yl]cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
Traditional Namepyrethrins
CAS Registry NumberNot Available
SMILES
[H]\C(CC1=C(C)[C@]([H])(CC1=O)OC(=O)[C@]1([H])[C@@]([H])(C=C(C)C)C1(C)C)=C(/[H])C=C
InChI Identifier
InChI=1S/C21H28O3/c1-7-8-9-10-15-14(4)18(12-17(15)22)24-20(23)19-16(11-13(2)3)21(19,5)6/h7-9,11,16,18-19H,1,10,12H2,2-6H3/b9-8-/t16-,18+,19+/m1/s1
InChI KeyROVGZAWFACYCSP-VUMXUWRFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrethrins. These are pyrethroids with a structure based on a skeleton that is characterized by the presence of a chrysanthemic acid esterified with a cyclopentenone derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentPyrethrins
Alternative Parents
Substituents
  • Pyrethrin-backbone
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclopropanecarboxylic acid or derivatives
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic 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
logP5.1ALOGPS
logP4.58ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)18.09ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity99.03 m³·mol⁻¹ChemAxon
Polarizability38.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPyrethrin I, 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 IDC00003056
Chemspider ID4444510
KEGG Compound IDC07594
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyrethrin I
METLIN IDNot Available
PubChem Compound5281045
PDB IDNot Available
ChEBI ID27815
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 ]