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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:55:18 UTC
Update Date2017-12-07 03:24:26 UTC
HMDB IDHMDB0033209
Secondary Accession Numbers
  • HMDB33209
Metabolite Identification
Common NameFenthion
DescriptionFenthion is an insecticide with low mammalian toxicity. Fenthion 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. (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
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
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
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
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
Chemical FormulaC10H15O3PS2
Average Molecular Weight278.328
Monoisotopic Molecular Weight278.020022238
IUPAC NameO,O-dimethyl O-3-methyl-4-(methylsulfanyl)phenyl phosphorothioate
Traditional NameO,O-dimethyl O-3-methyl-4-(methylsulfanyl)phenyl phosphorothioate
CAS Registry Number55-38-9
SMILES
COP(=S)(OC)OC1=CC=C(SC)C(C)=C1
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound 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:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point7.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0075 mg/mL at 20 °CNot Available
LogP4.09Not Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00os-4930000000-d917f6fe7c279d0326efView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00os-4930000000-d917f6fe7c279d0326efView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ik9-1970000000-38f4eb65b0f142b27c42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0090000000-cfc6cc7271f15039d91eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014j-0940000000-4c4cfaec8b9d90f02220View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gb9-0910000000-30762456be8c99676446View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gi0-0900000000-fc2e0d1f56a644607b35View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0g4i-0900000000-89a0ce8c9a4d4a49d57cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0290000000-9da11dc2725fc111b8c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0190000000-74fefa9007324dd9847eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-1970000000-6492e585fe189b3d02a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pc-9880000000-8949ee35385684bf0416View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-005c-0290000000-b55d858a805aaba2db82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-0290000000-6e342595466184c4595bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-2900000000-eb2a165616e3235fce1dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-7970000000-bc43a51c3e0e0f2a8537View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • 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
FoodDB IDFDB011222
KNApSAcK IDNot Available
Chemspider ID3229
KEGG Compound IDC14420
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFenthion
METLIN IDNot Available
PubChem Compound3346
PDB IDNot Available
ChEBI ID34761
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .