Showing Compound Card for Pyrethrins (CDB006319)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Not Available
Record Information
Version1.0
Created at2020-07-28 20:27:08 UTC
Updated at2020-11-18 16:40:18 UTC
CannabisDB IDCDB006319
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePyrethrins
DescriptionPyrethrins 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. Pyrethrins is possibly neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PyrethroidsMeSH
Chemical FormulaC43H56O8
Average Molecular Weight700.913
Monoisotopic Molecular Weight700.397518763
IUPAC Name(1S)-2-methyl-4-oxo-3-[(2E)-penta-2,4-dien-1-yl]cyclopent-2-en-1-yl (1R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate; 2-methyl-4-oxo-3-[(2E)-penta-2,4-dien-1-yl]cyclopent-2-en-1-yl (1R)-3-[(1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate
Traditional Name(1S)-2-methyl-4-oxo-3-[(2E)-penta-2,4-dien-1-yl]cyclopent-2-en-1-yl (1R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate; 2-methyl-4-oxo-3-[(2E)-penta-2,4-dien-1-yl]cyclopent-2-en-1-yl (1R)-3-[(1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate
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.[H]\C(CC1=C(C)C([H])(CC1=O)OC(=O)[C@]1([H])C([H])(C(\[H])=C(/C)C(=O)OC)C1(C)C)=C(\[H])C=C
InChI Identifier
InChI=1S/C22H28O5.C21H28O3/c1-7-8-9-10-15-14(3)18(12-17(15)23)27-21(25)19-16(22(19,4)5)11-13(2)20(24)26-6;1-7-8-9-10-15-14(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;7-9,11,16,18-19H,1,10,12H2,2-6H3/b9-8+,13-11+;9-8+/t16?,18?,19-;16?,18-,19-/m00/s1
InChI KeyVXSIXFKKSNGRRO-YWUDCVDHSA-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
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Carbocyclic fatty acid
  • Cyclopropanecarboxylic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Carboxylic acid ester
  • Ketone
  • Cyclic ketone
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
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
logP4.25ALOGPS
logP4.15ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)18.09ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.67 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity105.51 m³·mol⁻¹ChemAxon
Polarizability40.76 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
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 ID22901026
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyrethrin
METLIN IDNot Available
PubChem Compound71310221
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available