Cannabis Compound Database: Showing Compound Card for Fenvalerate (CDB006301)

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Record Information

Version

1.0

Created at

2020-07-28 20:25:58 UTC

Updated at

2020-11-18 16:40:17 UTC

CannabisDB ID

CDB006301

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Fenvalerate

Description

Fenvalerate, also known as pydrin or acadrex, 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 Fenvalerate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
alpha-Cyano-(3-phenoxyphenyl)methyl-4-chloro-alpha-(1-methylethyl)benzeneacetate	ChEBI
alpha-Cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyrate	ChEBI
alpha-Cyano-m-phenoxybenzyl 2-(p-chlorophenyl)-3-methylbutyrate	ChEBI
Phenvalerate	ChEBI
Pydrin	ChEBI
Acadrex	Kegg
a-Cyano-(3-phenoxyphenyl)methyl-4-chloro-a-(1-methylethyl)benzeneacetate	Generator
a-Cyano-(3-phenoxyphenyl)methyl-4-chloro-a-(1-methylethyl)benzeneacetic acid	Generator
alpha-Cyano-(3-phenoxyphenyl)methyl-4-chloro-alpha-(1-methylethyl)benzeneacetic acid	Generator
Α-cyano-(3-phenoxyphenyl)methyl-4-chloro-α-(1-methylethyl)benzeneacetate	Generator
Α-cyano-(3-phenoxyphenyl)methyl-4-chloro-α-(1-methylethyl)benzeneacetic acid	Generator
a-Cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyrate	Generator
a-Cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyric acid	Generator
alpha-Cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyric acid	Generator
Α-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyrate	Generator
Α-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyric acid	Generator
a-Cyano-m-phenoxybenzyl 2-(p-chlorophenyl)-3-methylbutyrate	Generator
a-Cyano-m-phenoxybenzyl 2-(p-chlorophenyl)-3-methylbutyric acid	Generator
alpha-Cyano-m-phenoxybenzyl 2-(p-chlorophenyl)-3-methylbutyric acid	Generator
Α-cyano-m-phenoxybenzyl 2-(p-chlorophenyl)-3-methylbutyrate	Generator
Α-cyano-m-phenoxybenzyl 2-(p-chlorophenyl)-3-methylbutyric acid	Generator
Phenvaleric acid	Generator
Fenvaleric acid	Generator
Agrofen	HMDB
alpha-cyano-3-Phenoxybenzyl 2-(4-chlorophenyl)isovalerate	HMDB
Aqmatrine	HMDB
Asana	HMDB
Belmark	HMDB, MeSH
cyano(3-Phenoxyphenyl)methyl 4-chloro-a-(1-methylethyl)benzeneacetate, 9ci	HMDB
Ectrin	HMDB
Esfenvalerate	HMDB, MeSH
Evercide 2362	HMDB
Fenaxin	HMDB
Fenkem	HMDB
Fenkill	HMDB
Fenoxin	HMDB
Fenval	HMDB
Phenoxin	HMDB
Sumicidin	HMDB, MeSH
Fenvalarate	MeSH, HMDB
alpha-cyano-3-Phenoxybenzyl 2-(4-chlorophenyl)-3- methylbutyrate	MeSH, HMDB
Pydrin, (R-(r,r))-isomer	MeSH, HMDB
Pydrin, (S-(r,r))-isomer	MeSH, HMDB
Sumi-alpha	MeSH, HMDB
alpha-cyano-3-Phenoxybenzyl alpha-isopropyl-4-chlorophenyl acetate	MeSH, HMDB
Pydrin, (R-(r,s))-isomer	MeSH, HMDB
Pydrin, (S-(r,s))-isomer	MeSH, HMDB

Chemical Formula

C₂₅H₂₂ClNO₃

Average Molecular Weight

419.9

Monoisotopic Molecular Weight

419.128821282

IUPAC Name

cyano(3-phenoxyphenyl)methyl 2-(4-chlorophenyl)-3-methylbutanoate

Traditional Name

tirade

CAS Registry Number

Not Available

SMILES

CC(C)C(C(=O)OC(C#N)C1=CC(OC2=CC=CC=C2)=CC=C1)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3

InChI Key

NYPJDWWKZLNGGM-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
Benzyloxycarbonyl
Phenylpropane
Phenoxy compound
Phenol ether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Nitrile
Carbonitrile
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organohalogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organochloride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:5014 )
carboxylic ester (CHEBI:5014 )
monochlorobenzenes (CHEBI:5014 )
Pyrethroid insecticides (C10988 )
Pyrethroid pesticides (C10988 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.3	ALOGPS
logP	6.61	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	10.62	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	59.32 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	116.33 m³·mol⁻¹	ChemAxon
Polarizability	43.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00or-2910100000-b8a7f37127eaef8c569e	2014-09-20	View Spectrum
Predicted GC-MS	alpha-Fenvalerate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0aor-3960000000-ede98846b29accb0213c	Spectrum
Predicted GC-MS	alpha-Fenvalerate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-Fenvalerate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-Fenvalerate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0411900000-52e6fc0c3b6bf03d7e0c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1911400000-22ea92c000b7ebbdd209	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kb-2900000000-261eba4b78d3491193c5	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0411900000-52e6fc0c3b6bf03d7e0c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1911400000-22ea92c000b7ebbdd209	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kb-2900000000-261eba4b78d3491193c5	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0010900000-719044399473cc10fb91	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014l-4443900000-c2b2a294f3547faa9c98	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9610000000-3bc7143c5e05c9a317a8	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0010900000-719044399473cc10fb91	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014l-4443900000-c2b2a294f3547faa9c98	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9610000000-3bc7143c5e05c9a317a8	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-0971700000-e1d0fb924d4c8c3aa703	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00or-0910000000-6dd73ae505d0f37939cc	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0920000000-ab183d0d2ab38ae2f6ee	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0aou-0890400000-f05c1fef2a5658843ae3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-2940300000-0599451e1ad86f10e978	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9110000000-2d94ef50fc108c410d10	2021-09-24	View Spectrum

NMR

Type	Description		View
1D NMR	¹³C NMR Spectrum (1D, 100.40 MHz, CDCl₃, experimental)		Spectrum

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

HMDB0253037

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008464

KNApSAcK ID

Not Available

Chemspider ID

3230

KEGG Compound ID

C10988

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fenvalerate

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

5014

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 Fenvalerate (CDB006301)

Structure for CDB006301 (Fenvalerate)