Cannabis Compound Database: Showing Compound Card for Allethrin (CDB006266)

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Record Information

Version

1.0

Created at

2020-07-28 20:23:47 UTC

Updated at

2020-11-18 16:40:16 UTC

CannabisDB ID

CDB006266

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Allethrin

Description

Allethrin, also known as pynamin or duocide, 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. Based on a literature review a significant number of articles have been published on Allethrin.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester	ChEBI
3-Allyl-2-methyl-4-oxo-2-cyclopenten-1-yl chrysanthemate	ChEBI
3-Allyl-2-methyl-4-oxocyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate	ChEBI
3-Allyl-4-keto-2-methylcyclopentenyl chrysanthemum monocarboxylate	ChEBI
Bioallethrin	ChEBI
Pynamin	ChEBI
Duocide	Kegg
2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester	Generator
3-Allyl-2-methyl-4-oxo-2-cyclopenten-1-yl chrysanthemic acid	Generator
3-Allyl-2-methyl-4-oxocyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylic acid	Generator
3-Allyl-4-keto-2-methylcyclopentenyl chrysanthemum monocarboxylic acid	Generator
Allethrins	MeSH
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester	MeSH

Chemical Formula

C₁₉H₂₆O₃

Average Molecular Weight

302.4079

Monoisotopic Molecular Weight

302.188194698

IUPAC Name

2-methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

Traditional Name

pyrethrin

CAS Registry Number

584-79-2

SMILES

CC(C)=CC1C(C(=O)OC2CC(=O)C(CC=C)=C2C)C1(C)C

InChI Identifier

InChI=1S/C19H26O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h7,9,14,16-17H,1,8,10H2,2-6H3

InChI Key

ZCVAOQKBXKSDMS-UHFFFAOYSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Pyrethroids

Alternative Parents

Substituents

Pyrethroid skeleton
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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

cyclopropanes (CHEBI:34572 )
Cyclopropane and cyclobutane monoterpenoids (C14337 )
Pyrethroid insecticides (C14337 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	-40°C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0046 mg/mL at 25°C [TOMLIN,C (1997)]	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.58	ALOGPS
logP	4.06	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	18.09	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	88.71 m³·mol⁻¹	ChemAxon
Polarizability	34.56 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0096-9500000000-70a98d42082c3f4b3c4e	2014-09-20	View Spectrum
Predicted GC-MS	Allethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-0f79-0901000000-317e8414ec3cd132d7d6	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-000i-0900000000-f5727e43a4d8157c607c	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-000i-0900000000-ccfeff4119a4c59853d8	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-000i-0900000000-d64f9f20926490a9787d	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 50V, positive	splash10-014r-0900000000-6acd9ccaecebc333612b	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 27V, positive	splash10-000i-0900000000-bc7a51d3398423a54c1e	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-014r-0900000000-6acd9ccaecebc333612b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-2c710a00995495b7f28d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-0900000000-aeb33847108dca4a3e1f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-0901000000-317e8414ec3cd132d7d6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-f5727e43a4d8157c607c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-0900000000-f92fa7a2cc19a82f4e76	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2956000000-ea6ab3754b3d6b73987b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-9410000000-f84a167828224c1c4c4d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zi0-9300000000-7aaddaff4b5285bab8da	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0419000000-e90978f635724728e791	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-5923000000-02cc94654ba7f61c64f0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00r2-3900000000-4ea3fa3c947c8af18c6c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-3891000000-eb1696e2adee8d74c943	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0cei-8911000000-52077304a781c1864357	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ap3-9500000000-ecaa094f13d20305c522	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0901000000-09a7aa08a386d1ad542c	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-a13a3b88213fa1a0638c	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-1930000000-adcb10f3f736d0680083	2021-10-12	View Spectrum

NMR

Type	Description		View

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0243551

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10958

KEGG Compound ID

C14337

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Allethrins

METLIN ID

Not Available

PubChem Compound

11442

PDB ID

Not Available

ChEBI ID

34572

References

General References

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 ]

Showing Compound Card for Allethrin (CDB006266)

Structure for CDB006266 (Allethrin)