Basic Info

Common NameFenthion(F04846)
2D Structure
Description

Fenthion is an organophosphate used primarily as an insecticide and secondarily as an avicide and acaricide. It was used extensively preharvest on sugar cane, rice, field corn, beets, pome and stone fruit, citrus fruits, pistachio, cotton, olives, coffee, cocoa, vegetables, and vines. However, fenthion no longer has Food and Drug Administration approval because of an excess number of poisoning related deaths (occur mostly by ingestion). Fenthion is neurotoxic. (L1682) (L1683)

FRCD IDF04846
CAS Number55-38-9
PubChem CID3346
FormulaC10H15O3PS2
IUPAC Name

dimethoxy-(3-methyl-4-methylsulfanylphenoxy)-sulfanylidene-$l^{5}-phosphane

InChI Key

PNVJTZOFSHSLTO-UHFFFAOYSA-N

InChI

InChI=1S/C10H15O3PS2/c1-8-7-9(5-6-10(8)16-4)13-14(15,11-2)12-3/h5-7H,1-4H3

Canonical SMILES

CC1=C(C=CC(=C1)OP(=S)(OC)OC)SC

Isomeric SMILES

CC1=C(C=CC(=C1)OP(=S)(OC)OC)SC

Synonyms
        
            fenthion
        
            Mercaptophos
        
            55-38-9
        
            Baytex
        
            Lebaycid
        
            Fenthione
        
            Phenthion
        
            Queletox
        
            Spotton
        
            Talodex
        
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
SubclassThiophosphoric acid esters
Intermediate Tree NodesAryl thiophosphates
Direct ParentPhenyl thiophosphates
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenyl 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
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.

Properties

Property NameProperty Value
Molecular Weight278.321
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Complexity254
Monoisotopic Mass278.02
Exact Mass278.02
XLogP4.1
Formal Charge0
Heavy Atom Count16
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9227
Human Intestinal AbsorptionHIA+0.9911
Caco-2 PermeabilityCaco2+0.5510
P-glycoprotein SubstrateNon-substrate0.8293
P-glycoprotein InhibitorInhibitor0.5000
Non-inhibitor0.9700
Renal Organic Cation TransporterNon-inhibitor0.8958
Distribution
Subcellular localizationMitochondria0.7610
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7312
CYP450 2D6 SubstrateNon-substrate0.6981
CYP450 3A4 SubstrateNon-substrate0.5055
CYP450 1A2 InhibitorInhibitor0.5625
CYP450 2C9 InhibitorNon-inhibitor0.5930
CYP450 2D6 InhibitorNon-inhibitor0.9325
CYP450 2C19 InhibitorInhibitor0.7066
CYP450 3A4 InhibitorInhibitor0.7959
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5889
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8616
Non-inhibitor0.8811
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.5413
Fish ToxicityHigh FHMT0.8409
Tetrahymena Pyriformis ToxicityLow TPT0.5145
Honey Bee ToxicityHigh HBT0.9620
BiodegradationNot ready biodegradable0.9626
Acute Oral ToxicityII0.4245
Carcinogenicity (Three-class)Non-required0.7137

Model Value Unit
Absorption
Aqueous solubility-4.6324LogS
Caco-2 Permeability1.0879LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.2285LD50, mol/kg
Fish Toxicity1.4198pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3137pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Chinese CabbageBritain0.01mg/kg
Other Small Fruit & Berries (Other Than Wild)Britain0.01mg/kg
Edible Olive Oil(Limited To Virgin Oil)Japan1ppm
Other Terrestrial Mammals,Edible OffalJapan0.2ppm
Pig,MuscleJapan0.5ppm
Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ...0120090European Union0.02*21/10/2011
Cherries (sweet) (Black cherries, Capulins, Chokecherries, Cornelian cherries/European corniols, Nanking cherries, Sour cherries/morello cherries,)0140020European Union0.01*21/10/2011
Plums (American plums, Beach plums, Cherry plums /myrabolans, Chickasaw plums, Chinese jujubes/red dates/Chinese dates, Damsons/ bullaces, Gages/greengages/Reine Claudes, Japanese plums, Klamath pl...0140040European Union0.01*21/10/2011
Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E...0154010European Union0.01*21/10/2011
Papayas (Akee apples, Feijoas/pineapple guavas, Langsats/lanzones/longkongs, Mangosteens, Naranjillas/lulos, Paw paws, Tamarillos,)0163040European Union0.01*21/10/2011
Cherimoyas (Elephant apples, Ilamas, Mammey sapotes, Marmeladedos, Pulasans, Rambutans/hairy litchis, Sapodillas, Sweetsops/sugar apples, Wild sweetsops/custard apples,)0163060European Union0.01*21/10/2011
Others (2)0233990European Union0.01*21/10/2011
Brassica vegetables (excluding brassica roots and brassica baby leaf crops)0240000European Union0.01*21/10/2011
Kales (Borecoles/collards greens/curly kales, Cow cabbages/stem kales, Cow cabbages/Jersey kales, Kohlrabies leaves (6), Rape kales/Siberian kales, Portuguese kales/tronchuda kales/Portuguese cabba...0243020European Union0.01*21/10/2011
Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L...0256080European Union0.01*21/10/2011
Pumpkin seeds (Watermelon seeds, Other seeds of species of familia Cucurbitaceae, not elsewhere mentioned,)0401100European Union0.02*21/10/2011
Apricots (Japanese apricots/Umes, Nectacots,)0140010European Union0.01*21/10/2011
Citrus fruits0110000European Union0.01*21/10/2011
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*21/10/2011
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*21/10/2011

References

TitleJournalDatePubmed ID
Evaluation of an acute oral gavage method for assessment of pesticide toxicity interrestrial amphibians.Environ Toxicol Chem2018 Feb28865127
Efficacy of Chemicals for the Potential Management of the Queensland Fruit FlyBactrocera tryoni (Froggatt) (Diptera: Tephritidae).Insects2017 May 928486404
Exploring pralidoxime chloride as a universal electrochemical probe fororganophosphorus pesticides detection.Anal Chim Acta2017 Aug 2228734368
In vivo tracing of organochloride and organophosphorus pesticides in differentorgans of hydroponically grown malabar spinach (Basella alba L.).J Hazard Mater2016 Oct 527209519
Organophosphate pesticide method development and presence of chlorpyrifos in the feet of nearctic-neotropical migratory songbirds from Canada that over-winter in Central America agricultural areas.Chemosphere2016 Feb26421621
Behavior of Multiclass Pesticide Residue Concentrations during the Transformationfrom Rose Petals to Rose Absolute.J Agric Food Chem2015 May 2725942486
Dielectric shell isolated and graphene shell isolated nanoparticle enhanced Ramanspectroscopies and their applications.Chem Soc Rev2015 Dec 726426491
Larvicidal activity and possible mode of action of four flavonoids and two fatty acids identified in Millettia pinnata seed toward three mosquito species.Parasit Vectors2015 Apr 1925928224
Molecularly imprinted polymer cartridges coupled to high performance liquidchromatography (HPLC-UV) for simple and rapid analysis of fenthion in olive oil.Talanta2014 Jul24840449
Detection of chemical residues in tangerine juices by a duplex immunoassay.Talanta2013 Nov 1524148369
Arrays on disc for screening and quantification of pollutants.Anal Chim Acta2013 Jun 1923746409
Spatiotemporal variation and risk assessment of pesticides in water of the lower catchment basin of Acheloos River, Western Greece.ScientificWorldJournal2013 Dec 2824453814
Insecticide susceptibility of Nezara viridula (Heteroptera: Pentatomidae) andthree other stink bug species composing a soybean pest complex in Japan.J Econ Entomol2012 Jun22812144
Larvicidal activity of Cnidium monnieri fruit coumarins and structurally related compounds against insecticide-susceptible and insecticide-resistant Culex pipiens pallens and Aedes aegypti.Pest Manag Sci2012 Jul22389164
Preparation and identification of generic antigens and broad-spectrum monoclonal antibodies for detection of organophosphorus pesticides.J AOAC Int2011 Nov-Dec22320100
Multi-residue analysis of pesticide residues in mangoes using solid-phasemicroextraction coupled to liquid chromatography and UV-Vis detection.J Sep Sci2011 Nov21919197
Larvicidal activity of Asarum heterotropoides root constituents against insecticide-susceptible and -resistant Culex pipiens pallens and Aedes aegypti and Ochlerotatus togoi.J Agric Food Chem2010 Sep 2220806890
Developing a systems approach for Sternochetus mangiferae (Coleoptera:Curculionidae) in South Africa.J Econ Entomol2010 Oct21061956
A new 1,3-dibutylimidazolium hexafluorophosphate ionic liquid-based dispersiveliquid-liquid microextraction to determine organophosphorus pesticides in waterand fruit samples by high-performance liquid chromatography.J Chromatogr A2010 Jul 3020580010
Microwave-assisted extraction at atmospheric pressure coupled to differentclean-up methods for the determination of organophosphorus pesticides in oliveand avocado oil.J Chromatogr A2009 Dec 1819926091

Targets

General Function:
Serine-type endopeptidase inhibitor activity
Specific Function:
Serine protease inhibitor. This inhibitor acts as 'bait' for tissue plasminogen activator, urokinase, protein C and matriptase-3/TMPRSS7. Its rapid interaction with PLAT may function as a major control point in the regulation of fibrinolysis.
Gene Name:
SERPINE1
Uniprot ID:
P05121
Molecular Weight:
45059.695 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Urokinase plasminogen activator receptor activity
Specific Function:
Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
Gene Name:
PLAUR
Uniprot ID:
Q03405
Molecular Weight:
36977.62 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Gene Name:
CCL2
Uniprot ID:
P13500
Molecular Weight:
11024.87 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Steroid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular Weight:
59590.91 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
Mechanism of Action:
Fenthion inhibits acetylcholinesterase.
References
  1. Marrs TC: Organophosphate poisoning. Pharmacol Ther. 1993;58(1):51-66. [8415873 ]
General Function:
Steroid hydroxylase activity
Specific Function:
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible for the epoxidation of endogenous cardiac arachidonic acid pools.
Gene Name:
CYP2J2
Uniprot ID:
P51589
Molecular Weight:
57610.165 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]