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Showing Compound Fenthion (FDB011222)

Record Information
Version1.0
Creation date2010-04-08 22:09:32 UTC
Update date2018-05-29 00:51:52 UTC
Primary IDFDB011222
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFenthion
DescriptionInsecticide with low mammalian toxicity. It is used in agriculture and against mosquito larvae in tropical fresh waters Fenthion is an organothiophosphate insecticide, avicide, and acaricide. Like most other organophosphates, its mode of action is via cholinesterase inhibition. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as moderately toxic compound in U.S. Environmental Protection Agency? and World Health Organization toxicity class.
CAS Number55-38-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4-Methylmercapto-3-methylphenyl dimethyl thiophosphateChEBI
MercaptophosChEBI
MPPChEBI
O,O-Dimethyl O-4-(methylmercapto)-3-methylphenyl phosphorothioateChEBI
O,O-Dimethyl O-4-methylthio-m-tolyl phosphorothioateChEBI
O,O-Dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] thiophosphateChEBI
O,O-Dimethyl-O-4-(methylmercapto)-3-methylphenyl thiophosphateChEBI
Phosphorothioic acid, O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl) esterChEBI
TiguvonKegg
4-Methylmercapto-3-methylphenyl dimethyl thiophosphoric acidGenerator
O,O-Dimethyl O-4-(methylmercapto)-3-methylphenyl phosphorothioic acidGenerator
O,O-Dimethyl O-4-methylthio-m-tolyl phosphorothioic acidGenerator
O,O-Dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] thiophosphoric acidGenerator
O,O-Dimethyl O-[3-methyl-4-(methylsulphanyl)phenyl] thiophosphateGenerator
O,O-Dimethyl O-[3-methyl-4-(methylsulphanyl)phenyl] thiophosphoric acidGenerator
O,O-Dimethyl-O-4-(methylmercapto)-3-methylphenyl thiophosphoric acidGenerator
Phosphorothioate, O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl) esterGenerator
Bayer 29493HMDB
BaytexHMDB, MeSH
Dimethyl (3-methyl-4-(methylthio)phenyl) phosphorothionateHMDB
Dimethyl methylthiotolyl phosphorothioateHMDB
Dimethyl O-(3-methyl-4-(methylthio)phenyl) thiophosphateHMDB
Dimethyl O-(4-(methylthio)-m-tolyl) phosphorothioateHMDB
DMTPHMDB
ent 25540HMDB
EntexHMDB
FenthioneHMDB
FiguronHMDB
LebaycidHMDB, MeSH
LebayeidHMDB
Mosquitocide 700HMDB
MPP (Pesticide)HMDB
O,O-Dimethyl O-(4-methylthio-3-methylphenyl) thiophosphateHMDB
O,O-Dimethyl O-[(3-methyl-4-methylthio)phenyl] phosphorothioate, 9ciHMDB
O,O-Dimethyl-O-[4-(methylthio)-m-tolyl] phosphorothioateHMDB
PhenthionHMDB
QueletoxHMDB
SpottonHMDB
TalodexHMDB
4-Methylmercapto-3-methylphenyl dimethyl thioateChEBI
4-Methylmercapto-3-methylphenyl dimethyl thioic acidGenerator
Dimethyl (3-methyl-4-(methylthio)phenyl) orothionateHMDB
Dimethyl methylthiotolyl orothioateHMDB
Dimethyl O-(3-methyl-4-(methylthio)phenyl) thioateHMDB
Dimethyl O-(4-(methylthio)-m-tolyl) orothioateHMDB
ENT 25540db_source
MPP (pesticide)biospider
O,O-Dimethyl O-(4-methylthio-3-methylphenyl) thioateHMDB
O,O-Dimethyl O-[(3-methyl-4-methylthio)phenyl] orothioate, 9ciHMDB
O,O-Dimethyl O-[(3-methyl-4-methylthio)phenyl] phosphorothioate, 9CIdb_source
O,O-Dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] thioateChEBI
O,O-Dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] thioic acidGenerator
O,O-Dimethyl O-[3-methyl-4-(methylsulphanyl)phenyl] thioateGenerator
O,O-Dimethyl O-[3-methyl-4-(methylsulphanyl)phenyl] thioic acidGenerator
O,O-Dimethyl O-4-(methylmercapto)-3-methylphenyl orothioateChEBI
O,O-Dimethyl O-4-(methylmercapto)-3-methylphenyl orothioic acidGenerator
O,O-Dimethyl O-4-methylthio-m-tolyl orothioateChEBI
O,O-Dimethyl O-4-methylthio-m-tolyl orothioic acidGenerator
O,O-Dimethyl-O-[4-(methylthio)-m-tolyl] orothioateHMDB
O,O-Dimethyl-O-4-(methylmercapto)-3-methylphenyl thioateChEBI
O,O-Dimethyl-O-4-(methylmercapto)-3-methylphenyl thioic acidGenerator
Orothioate, O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl) esterGenerator
Orothioic acid, O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl) esterChEBI
Predicted Properties
PropertyValueSource
Water Solubility0.0042 g/LALOGPS
logP3.93ALOGPS
logP3.8ChemAxon
logS-4.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.67 m³·mol⁻¹ChemAxon
Polarizability27.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H15O3PS2
IUPAC nameO,O-dimethyl O-3-methyl-4-(methylsulfanyl)phenyl phosphorothioate
InChI IdentifierInChI=1S/C10H15O3PS2/c1-8-7-9(5-6-10(8)16-4)13-14(15,11-2)12-3/h5-7H,1-4H3
InChI KeyPNVJTZOFSHSLTO-UHFFFAOYSA-N
Isomeric SMILESCOP(=S)(OC)OC1=CC=C(SC)C(C)=C1
Average Molecular Weight278.328
Monoisotopic Molecular Weight278.020022238
Classification
Description Belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
Sub ClassThiophosphoric acid esters
Direct ParentPhenyl thiophosphates
Alternative Parents
Substituents
  • Phenyl thiophosphate
  • Phenoxy compound
  • Aryl thioether
  • Thiophosphate triester
  • Thiophenol ether
  • Toluene
  • Alkylarylthioether
  • Monocyclic benzene moiety
  • Benzenoid
  • Thioether
  • Sulfenyl compound
  • Organosulfur compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 43.15%; H 5.43%; O 17.24%; P 11.13%; S 23.04%DFC
Melting Point7.5 oC
Boiling PointBp0.01 87°DFC
Experimental Water Solubility0.0075 mg/mL at 20 oCBOWMAN,BT & SANS,WW (1983)
Experimental logP4.09HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 1.25DFC
Refractive Indexn20D 1.5698DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004i-7970000000-bc43a51c3e0e0f2a85372014-09-20View Spectrum
GC-MSFenthion, non-derivatized, GC-MS Spectrumsplash10-00os-4930000000-d917f6fe7c279d0326efSpectrum
GC-MSFenthion, non-derivatized, GC-MS Spectrumsplash10-00os-4930000000-d917f6fe7c279d0326efSpectrum
Predicted GC-MSFenthion, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ik9-1970000000-38f4eb65b0f142b27c42Spectrum
Predicted GC-MSFenthion, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFenthion, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0090000000-cfc6cc7271f15039d91e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014j-0940000000-4c4cfaec8b9d90f022202017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gb9-0910000000-30762456be8c996764462017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gi0-0900000000-fc2e0d1f56a644607b352017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0g4i-0900000000-89a0ce8c9a4d4a49d57c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0290000000-9da11dc2725fc111b8c42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014j-0940000000-199b003861522f4b62e12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0gb9-0910000000-14a50b7ed49de35229bc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0gi0-0900000000-fc2e0d1f56a644607b352021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0g4i-0900000000-daf8e3082dcd599a9ef62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0g4i-0900000000-677923a06bbdab3e4faa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0v4i-0910000000-d74e5478dcae4fb77f712021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0g4i-0900000000-c7ed3dac5d73de1abfe22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-0290000000-c4282f269db3a3c433b72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014j-0940000000-49b2bd577f2239e1eeed2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-03e61a06874c5e65189c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0g4i-0900000000-89a0ce8c9a4d4a49d57c2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0190000000-74fefa9007324dd9847e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-1970000000-6492e585fe189b3d02a02016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pc-9880000000-8949ee35385684bf04162016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-005c-0290000000-b55d858a805aaba2db822016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-0290000000-6e342595466184c4595b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-2900000000-eb2a165616e3235fce1d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0190000000-953bec3de0724b9038a42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004u-4790000000-c6f5d3f2adc0c2093b0b2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100.40 MHz, CDCl3, experimental)Spectrum
ChemSpider ID3229
ChEMBL IDCHEMBL1604375
KEGG Compound IDC14420
Pubchem Compound ID3346
Pubchem Substance IDNot Available
ChEBI ID34761
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33209
CRC / DFC (Dictionary of Food Compounds) IDGGJ54-N:GGJ54-N
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDFenthion
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference