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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:55:18 UTC
Update Date2022-03-07 02:53:37 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
Data?1563862369
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
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
Chemical FormulaC10H15O3PS2
Average Molecular Weight278.328
Monoisotopic Molecular Weight278.020022238
IUPAC NameO,O-dimethyl O-3-methyl-4-(methylsulfanyl)phenyl phosphorothioate
Traditional Namefenthion
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
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
Disposition

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point7.5 °CNot Available
Boiling Point251.00 to 253.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.0075 mg/mL at 20 °CNot Available
LogP4.09Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+162.6131661259
DarkChem[M-H]-159.93331661259
DeepCCS[M+H]+156.31930932474
DeepCCS[M-H]-153.96130932474
DeepCCS[M-2H]-187.05130932474
DeepCCS[M+Na]+162.41230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FenthionCOP(=S)(OC)OC1=CC=C(SC)C(C)=C12826.4Standard polar33892256
FenthionCOP(=S)(OC)OC1=CC=C(SC)C(C)=C11961.7Standard non polar33892256
FenthionCOP(=S)(OC)OC1=CC=C(SC)C(C)=C11979.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Fenthion EI-B (Non-derivatized)splash10-00os-4930000000-d917f6fe7c279d0326ef2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fenthion EI-B (Non-derivatized)splash10-00os-4930000000-d917f6fe7c279d0326ef2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fenthion GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ik9-1970000000-38f4eb65b0f142b27c422017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fenthion GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fenthion GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-7970000000-bc43a51c3e0e0f2a85372014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion LC-ESI-QTOF , positive-QTOFsplash10-004i-0090000000-cfc6cc7271f15039d91e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion LC-ESI-QTOF , positive-QTOFsplash10-014j-0940000000-4c4cfaec8b9d90f022202017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion LC-ESI-QTOF , positive-QTOFsplash10-0gb9-0910000000-30762456be8c996764462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion LC-ESI-QTOF , positive-QTOFsplash10-0gi0-0900000000-fc2e0d1f56a644607b352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion LC-ESI-QTOF , positive-QTOFsplash10-0g4i-0900000000-89a0ce8c9a4d4a49d57c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion LC-ESI-QFT , positive-QTOFsplash10-001i-0290000000-9da11dc2725fc111b8c42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion 20V, Positive-QTOFsplash10-014j-0940000000-199b003861522f4b62e12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion 30V, Positive-QTOFsplash10-0gb9-0910000000-14a50b7ed49de35229bc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion 40V, Positive-QTOFsplash10-0gi0-0900000000-fc2e0d1f56a644607b352021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion 50V, Positive-QTOFsplash10-0g4i-0900000000-daf8e3082dcd599a9ef62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion 50V, Positive-QTOFsplash10-0g4i-0900000000-677923a06bbdab3e4faa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion 30V, Positive-QTOFsplash10-0v4i-0910000000-d74e5478dcae4fb77f712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion 40V, Positive-QTOFsplash10-0g4i-0900000000-c7ed3dac5d73de1abfe22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion 35V, Positive-QTOFsplash10-001i-0290000000-c4282f269db3a3c433b72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion 20V, Positive-QTOFsplash10-014j-0940000000-49b2bd577f2239e1eeed2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion 10V, Positive-QTOFsplash10-004i-0090000000-03e61a06874c5e65189c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenthion 50V, Positive-QTOFsplash10-0g4i-0900000000-89a0ce8c9a4d4a49d57c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenthion 10V, Positive-QTOFsplash10-004i-0190000000-74fefa9007324dd9847e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenthion 20V, Positive-QTOFsplash10-002r-1970000000-6492e585fe189b3d02a02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenthion 40V, Positive-QTOFsplash10-01pc-9880000000-8949ee35385684bf04162016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenthion 10V, Negative-QTOFsplash10-005c-0290000000-b55d858a805aaba2db822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenthion 20V, Negative-QTOFsplash10-003r-0290000000-6e342595466184c4595b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenthion 40V, Negative-QTOFsplash10-0a4l-2900000000-eb2a165616e3235fce1d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenthion 10V, Positive-QTOFsplash10-004i-0190000000-953bec3de0724b9038a42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenthion 20V, Positive-QTOFsplash10-004u-4790000000-c6f5d3f2adc0c2093b0b2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDDB11412
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1045951
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.. .