Cannabis Compound Database: Showing Compound Card for Phenothrin (CDB006274)

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Record Information

Version

1.0

Created at

2020-07-28 20:24:17 UTC

Updated at

2020-11-18 16:40:16 UTC

CannabisDB ID

CDB006274

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Phenothrin

Description

Phenothrin, also known as sumithrin or hegor antipoux, 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 Phenothrin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid (3-phenoxyphenyl)methyl ester	ChEBI
Sumithrin	ChEBI
Hegor antipoux	Kegg
2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (3-phenoxyphenyl)methyl ester	Generator
(3-Phenoxyphenyl)methyl cis,trans-(+)-2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate	MeSH
D-Phenothrin	MeSH
Phenothrin, (1R-cis)-isomer	MeSH
Phenothrin, (1R-trans)-isomer	MeSH
Phenothrin, (1S-cis)-isomer	MeSH
Phenothrin, (1S-trans)-isomer	MeSH
Phenothrin, (cis-(+-))-isomer	MeSH
Phenothrin, (trans-(+-))-isomer	MeSH
m-Phenoxybenzyl (1R-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid	Generator

Chemical Formula

C₂₃H₂₆O₃

Average Molecular Weight

350.4507

Monoisotopic Molecular Weight

350.188194698

IUPAC Name

(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

Traditional Name

phenothrin

CAS Registry Number

26002-80-2

SMILES

CC(C)=CC1C(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

InChI Key

SBNFWQZLDJGRLK-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
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 Framework

Aromatic homomonocyclic compounds

External Descriptors

cyclopropanes (CHEBI:34916 )
Pyrethroid insecticides (C14387 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	< 25°C	Not Available
Boiling Point	>290°C	Not Available
Water Solubility	9.7e-06 mg/mL at 25°C [TOMLIN,C (1997); <9.7 ug/L]	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.42	ALOGPS
logP	5.57	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.84 m³·mol⁻¹	ChemAxon
Polarizability	39.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00e9-5900000000-82828ceb9c78ca715405	2014-09-20	View Spectrum
Predicted GC-MS	Phenothrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phenothrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phenothrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phenothrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0a4i-0009000000-40229bc9204047a90696	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0a4i-0009000000-ef289d9b6c43e9ffbab1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0002-0009000000-aaf1dcdf1335b088a86b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4i-0009000000-b8fdf60d2da1b9af6def	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0a6u-0900000000-c9855a3f9fc537fb0bcf	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0a4l-0900000000-efa2e4a7c20189b908ea	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0409000000-29f91143368a5e163638	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-3935000000-1f5ba52cfd1331e3c829	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pvi-7900000000-a7c057d4e94614b05bf6	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0109000000-2146ad06bc95b25bf442	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-2809000000-986cbdb101e42868e61b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-8f041a7fa0db67d9ea24	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f7k-2794000000-e3308d4427a553ee9e33	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2913000000-92692d151e0539f88ca0	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-7900000000-c59f160f7452c1b7d545	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0309000000-1a857626b5331003790e	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0901000000-e1b9792b83ff015d64f7	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9322000000-254c9ac19a5f51b0b4b2	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

HMDB0250789

DrugBank ID

DB13717

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB007353

KNApSAcK ID

Not Available

Chemspider ID

4603

KEGG Compound ID

C14387

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenothrin

METLIN ID

Not Available

PubChem Compound

4767

PDB ID

Not Available

ChEBI ID

34916

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 Phenothrin (CDB006274)

Structure for CDB006274 (Phenothrin)