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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:46:28 UTC
Update Date2017-12-07 04:29:22 UTC
HMDB IDHMDB0041893
Secondary Accession Numbers
  • HMDB41893
Metabolite Identification
Common NameFenitrothion
DescriptionFenitrothion, also known as metathion or MEP, 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. Fenitrothion exists as a liquid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, fenitrothion is primarily located in the membrane (predicted from logP). Fenitrothion can be biosynthesized from 4-nitro-m-cresol. Fenitrothion is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
MEPChEBI
O,O-Dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioateChEBI
O,O-Dimethyl O-(3-methyl-4-nitrophenyl) thiophosphateChEBI
O,O-Dimethyl O-4-nitro-m-tolyl phosphorothioateChEBI
O,O-Dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioic acidGenerator
O,O-Dimethyl O-(3-methyl-4-nitrophenyl) thiophosphoric acidGenerator
O,O-Dimethyl O-4-nitro-m-tolyl phosphorothioic acidGenerator
AccothionHMDB
AceothionHMDB
Agriya 1050HMDB
AgrothionHMDB
AkotionHMDB
American cyanamid CL-47,300HMDB
ArbogalHMDB
Bayer S 5660HMDB
Bis-fenitrothionHMDB
CekutrothionHMDB
CyfenHMDB
CytelHMDB
CytenHMDB
DicofenHMDB
Dimethyl 3-methyl-4-nitrophenyl phosphorothionateHMDB
Dimethyl 4-nitro-m-tolyl phosphorothionateHMDB
FalithionHMDB
FenitoxHMDB
FenitrotionHMDB
FolithionHMDB
Folithion ec 50HMDB
KotionHMDB
MacbarHMDB
MEP (pesticide)HMDB
MEP (phosphorus insecticide)HMDB
metathio e-50HMDB
MetathionHMDB
Metathion e-50HMDB
MetathioneHMDB
MetathionineHMDB
Metathionine e-50HMDB
MetationHMDB
Metation e-50HMDB
MethylnitrophosHMDB
Mglawik FHMDB
NitrophosHMDB
NovathionHMDB
NuvanolHMDB
O,O-DiMe O-(3-methyl-4-nitrophenyl) thiophosphateHMDB
O,O-Dimethyl O-(3-methyl-4-nitrophenyl)phosphorothioateHMDB
O,O-Dimethyl O-(4-nitro-3-methylphenyl)thiophosphateHMDB
O,O-Dimethyl O-4-nitro-m-tolyl thiophosphateHMDB
O,O-Dimethyl-O-(3-methyl-4-nitro-phenyl)-monothiophosphateHMDB
O,O-Dimethyl-O-(3-methyl-4-nitrofenyl)-monothiofosfaatHMDB
O,O-Dimethyl-O-(4-nitro-5-methylphenyl)-thionophosphateHMDB
O,O-Dimetil-O-(3-metil-4-nitro-fenil)-monotiofosfatoHMDB
O,O-Dimetil-O-(3-metil-4-nitrofenil) fosforotioatoHMDB
OleometathionHMDB
OleosumifeneHMDB
OvadofosHMDB
OwadofosHMDB
OwadophosHMDB
Pennwalt C-4852HMDB
PhenitrothionHMDB
SumifeneHMDB
SumigranHMDB
SumithianHMDB
SumithionHMDB
sumitomo S-1102aHMDB
Tionfos 50 leHMDB
VerthionHMDB
1050, AgriaMeSH
Agria 1050MeSH
SumithioneMeSH
Chemical FormulaC9H12NO5PS
Average Molecular Weight277.234
Monoisotopic Molecular Weight277.017379701
IUPAC NameO,O-dimethyl O-3-methyl-4-nitrophenyl phosphorothioate
Traditional NameO,O-dimethyl O-3-methyl-4-nitrophenyl phosphorothioate
CAS Registry Number122-14-5
SMILES
COP(=S)(OC)OC1=CC=C(C(C)=C1)N(=O)=O
InChI Identifier
InChI=1S/C9H12NO5PS/c1-7-6-8(4-5-9(7)10(11)12)15-16(17,13-2)14-3/h4-6H,1-3H3
InChI KeyZNOLGFHPUIJIMJ-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
  • Nitrobenzene
  • Nitrotoluene
  • Phenoxy compound
  • Nitroaromatic compound
  • Thiophosphate triester
  • Toluene
  • Monocyclic benzene moiety
  • Benzenoid
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Environmental role:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point3.4 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.038 mg/mL at 25 °CNot Available
LogP3.30Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP3.31ALOGPS
logP3.12ChemAxon
logS-4.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area73.51 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity68.23 m³·mol⁻¹ChemAxon
Polarizability24.74 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)splash10-01tc-9540000000-a180b7cec61770691237View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-1980000000-469fd8d8b5afef55db6dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01tc-9540000000-a180b7cec61770691237View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-1980000000-469fd8d8b5afef55db6dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-3950000000-0b6ab147cddeb288eed5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-2848423a70610d0dae28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0090000000-d10a1515515bbdc69975View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-3940000000-5cc3638b33f222c4352cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0390000000-e49f20ded24e19945287View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0490000000-c57ad69bf50c72792ac7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1900000000-d97d44855ea21933b936View in MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-8980000000-4c5af1b2fb42bdb10504View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID28941
KEGG Compound IDC14442
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFenitrothion
METLIN IDNot Available
PubChem Compound31200
PDB IDNot Available
ChEBI ID34757
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available