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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:29 UTC
Update Date2021-09-14 15:45:26 UTC
HMDB IDHMDB0031791
Secondary Accession Numbers
  • HMDB31791
Metabolite Identification
Common NameFenvalerate
DescriptionFenvalerate, 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 small amount of articles have been published on Fenvalerate.
Structure
Data?1563862171
Synonyms
ValueSource
alpha-Cyano-(3-phenoxyphenyl)methyl-4-chloro-alpha-(1-methylethyl)benzeneacetateChEBI
alpha-Cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyrateChEBI
alpha-Cyano-m-phenoxybenzyl 2-(p-chlorophenyl)-3-methylbutyrateChEBI
PhenvalerateChEBI
PydrinChEBI
AcadrexKegg
a-Cyano-(3-phenoxyphenyl)methyl-4-chloro-a-(1-methylethyl)benzeneacetateGenerator
a-Cyano-(3-phenoxyphenyl)methyl-4-chloro-a-(1-methylethyl)benzeneacetic acidGenerator
alpha-Cyano-(3-phenoxyphenyl)methyl-4-chloro-alpha-(1-methylethyl)benzeneacetic acidGenerator
Α-cyano-(3-phenoxyphenyl)methyl-4-chloro-α-(1-methylethyl)benzeneacetateGenerator
Α-cyano-(3-phenoxyphenyl)methyl-4-chloro-α-(1-methylethyl)benzeneacetic acidGenerator
a-Cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyrateGenerator
a-Cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyric acidGenerator
alpha-Cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyric acidGenerator
Α-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyrateGenerator
Α-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyric acidGenerator
a-Cyano-m-phenoxybenzyl 2-(p-chlorophenyl)-3-methylbutyrateGenerator
a-Cyano-m-phenoxybenzyl 2-(p-chlorophenyl)-3-methylbutyric acidGenerator
alpha-Cyano-m-phenoxybenzyl 2-(p-chlorophenyl)-3-methylbutyric acidGenerator
Α-cyano-m-phenoxybenzyl 2-(p-chlorophenyl)-3-methylbutyrateGenerator
Α-cyano-m-phenoxybenzyl 2-(p-chlorophenyl)-3-methylbutyric acidGenerator
Phenvaleric acidGenerator
Fenvaleric acidGenerator
AgrofenHMDB
alpha-cyano-3-Phenoxybenzyl 2-(4-chlorophenyl)isovalerateHMDB
AqmatrineHMDB
AsanaHMDB
BelmarkHMDB, MeSH
cyano(3-Phenoxyphenyl)methyl 4-chloro-a-(1-methylethyl)benzeneacetate, 9ciHMDB
EctrinHMDB
EsfenvalerateHMDB, MeSH
Evercide 2362HMDB
FenaxinHMDB
FenkemHMDB
FenkillHMDB
FenoxinHMDB
FenvalHMDB
PhenoxinHMDB
SumicidinHMDB, MeSH
FenvalarateMeSH, HMDB
alpha-cyano-3-Phenoxybenzyl 2-(4-chlorophenyl)-3- methylbutyrateMeSH, HMDB
Pydrin, (R-(r*,r*))-isomerMeSH, HMDB
Pydrin, (S-(r*,r*))-isomerMeSH, HMDB
Sumi-alphaMeSH, HMDB
alpha-cyano-3-Phenoxybenzyl alpha-isopropyl-4-chlorophenyl acetateMeSH, HMDB
Pydrin, (R-(r*,s*))-isomerMeSH, HMDB
Pydrin, (S-(r*,s*))-isomerMeSH, HMDB
Chemical FormulaC25H22ClNO3
Average Molecular Weight419.9
Monoisotopic Molecular Weight419.128821282
IUPAC Namecyano(3-phenoxyphenyl)methyl 2-(4-chlorophenyl)-3-methylbutanoate
Traditional Nametirade
CAS Registry Number51630-58-1
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 KeyNYPJDWWKZLNGGM-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentPyrethroids
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Environmental role:

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point39.5 - 53.7 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.20Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00082 g/LALOGPS
logP6.3ALOGPS
logP6.61ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)10.62ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.32 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity116.33 m³·mol⁻¹ChemAxon
Polarizability43.1 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-3960000000-ede98846b29accb0213c2017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00or-2910100000-b8a7f37127eaef8c569e2014-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0411900000-52e6fc0c3b6bf03d7e0c2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1911400000-22ea92c000b7ebbdd2092015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-2900000000-261eba4b78d3491193c52015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0411900000-52e6fc0c3b6bf03d7e0c2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1911400000-22ea92c000b7ebbdd2092015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-2900000000-261eba4b78d3491193c52015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0010900000-719044399473cc10fb912015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014l-4443900000-c2b2a294f3547faa9c982015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9610000000-3bc7143c5e05c9a317a82015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0010900000-719044399473cc10fb912015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014l-4443900000-c2b2a294f3547faa9c982015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9610000000-3bc7143c5e05c9a317a82015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0971700000-e1d0fb924d4c8c3aa7032021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0910000000-6dd73ae505d0f37939cc2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0920000000-ab183d0d2ab38ae2f6ee2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aou-0890400000-f05c1fef2a5658843ae32021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2940300000-0599451e1ad86f10e9782021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9110000000-2d94ef50fc108c410d102021-09-08View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR13C NMR Spectrum (1D, 100.40 MHz, CDCl3, experimental)2014-09-23View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008464
KNApSAcK IDNot Available
Chemspider ID3230
KEGG Compound IDC10988
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFenvalerate
METLIN IDNot Available
PubChem Compound3347
PDB IDNot Available
ChEBI ID5014
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Qu JH, Hong X, Chen JF, Wang YB, Sun H, Xu XL, Song L, Wang SL, Wang XR: Fenvalerate inhibits progesterone production through cAMP-dependent signal pathway. Toxicol Lett. 2008 Jan 4;176(1):31-9. Epub 2007 Sep 21. [PubMed:18053657 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.