Showing Compound Fenthion (FDB011222)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:32 UTC

Update date

2018-05-29 00:51:52 UTC

Primary ID

FDB011222

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Fenthion

Description

Insecticide 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 Number

55-38-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4-Methylmercapto-3-methylphenyl dimethyl thiophosphate	ChEBI
Mercaptophos	ChEBI
MPP	ChEBI
O,O-Dimethyl O-4-(methylmercapto)-3-methylphenyl phosphorothioate	ChEBI
O,O-Dimethyl O-4-methylthio-m-tolyl phosphorothioate	ChEBI
O,O-Dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] thiophosphate	ChEBI
O,O-Dimethyl-O-4-(methylmercapto)-3-methylphenyl thiophosphate	ChEBI
Phosphorothioic acid, O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl) ester	ChEBI
Tiguvon	Kegg
4-Methylmercapto-3-methylphenyl dimethyl thiophosphoric acid	Generator
O,O-Dimethyl O-4-(methylmercapto)-3-methylphenyl phosphorothioic acid	Generator
O,O-Dimethyl O-4-methylthio-m-tolyl phosphorothioic acid	Generator
O,O-Dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] thiophosphoric acid	Generator
O,O-Dimethyl O-[3-methyl-4-(methylsulphanyl)phenyl] thiophosphate	Generator
O,O-Dimethyl O-[3-methyl-4-(methylsulphanyl)phenyl] thiophosphoric acid	Generator
O,O-Dimethyl-O-4-(methylmercapto)-3-methylphenyl thiophosphoric acid	Generator
Phosphorothioate, O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl) ester	Generator
Bayer 29493	HMDB
Baytex	HMDB, MeSH
Dimethyl (3-methyl-4-(methylthio)phenyl) phosphorothionate	HMDB
Dimethyl methylthiotolyl phosphorothioate	HMDB
Dimethyl O-(3-methyl-4-(methylthio)phenyl) thiophosphate	HMDB
Dimethyl O-(4-(methylthio)-m-tolyl) phosphorothioate	HMDB
DMTP	HMDB
ent 25540	HMDB
Entex	HMDB
Fenthione	HMDB
Figuron	HMDB
Lebaycid	HMDB, MeSH
Lebayeid	HMDB
Mosquitocide 700	HMDB
MPP (Pesticide)	HMDB
O,O-Dimethyl O-(4-methylthio-3-methylphenyl) thiophosphate	HMDB
O,O-Dimethyl O-[(3-methyl-4-methylthio)phenyl] phosphorothioate, 9ci	HMDB
O,O-Dimethyl-O-[4-(methylthio)-m-tolyl] phosphorothioate	HMDB
Phenthion	HMDB
Queletox	HMDB
Spotton	HMDB
Talodex	HMDB
4-Methylmercapto-3-methylphenyl dimethyl thioate	ChEBI
4-Methylmercapto-3-methylphenyl dimethyl thioic acid	Generator
Dimethyl (3-methyl-4-(methylthio)phenyl) orothionate	HMDB
Dimethyl methylthiotolyl orothioate	HMDB
Dimethyl O-(3-methyl-4-(methylthio)phenyl) thioate	HMDB
Dimethyl O-(4-(methylthio)-m-tolyl) orothioate	HMDB
ENT 25540	db_source
MPP (pesticide)	biospider
O,O-Dimethyl O-(4-methylthio-3-methylphenyl) thioate	HMDB
O,O-Dimethyl O-[(3-methyl-4-methylthio)phenyl] orothioate, 9ci	HMDB
O,O-Dimethyl O-[(3-methyl-4-methylthio)phenyl] phosphorothioate, 9CI	db_source
O,O-Dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] thioate	ChEBI
O,O-Dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] thioic acid	Generator
O,O-Dimethyl O-[3-methyl-4-(methylsulphanyl)phenyl] thioate	Generator
O,O-Dimethyl O-[3-methyl-4-(methylsulphanyl)phenyl] thioic acid	Generator
O,O-Dimethyl O-4-(methylmercapto)-3-methylphenyl orothioate	ChEBI
O,O-Dimethyl O-4-(methylmercapto)-3-methylphenyl orothioic acid	Generator
O,O-Dimethyl O-4-methylthio-m-tolyl orothioate	ChEBI
O,O-Dimethyl O-4-methylthio-m-tolyl orothioic acid	Generator
O,O-Dimethyl-O-[4-(methylthio)-m-tolyl] orothioate	HMDB
O,O-Dimethyl-O-4-(methylmercapto)-3-methylphenyl thioate	ChEBI
O,O-Dimethyl-O-4-(methylmercapto)-3-methylphenyl thioic acid	Generator
Orothioate, O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl) ester	Generator
Orothioic acid, O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl) ester	ChEBI

Predicted Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	3.93	ALOGPS
logP	3.8	ChemAxon
logS	-4.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.67 m³·mol⁻¹	ChemAxon
Polarizability	27.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H15O3PS2

IUPAC name

O,O-dimethyl O-3-methyl-4-(methylsulfanyl)phenyl phosphorothioate

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 Key

PNVJTZOFSHSLTO-UHFFFAOYSA-N

Isomeric SMILES

COP(=S)(OC)OC1=CC=C(SC)C(C)=C1

Average Molecular Weight

278.328

Monoisotopic Molecular Weight

278.020022238

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic thiophosphoric acids and derivatives

Sub Class

Thiophosphoric acid esters

Direct Parent

Phenyl 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

organic thiophosphate (CHEBI:34761 )
Organophosphorus insecticides (C14420 )

Ontology

Ingestion

Biological location:

Subcellular:

Source:

Food

Role

Environmental role:

Environmental contaminant

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 43.15%; H 5.43%; O 17.24%; P 11.13%; S 23.04%	DFC
Melting Point	7.5 oC
Boiling Point	Bp0.01 87°	DFC
Experimental Water Solubility	0.0075 mg/mL at 20 oC	BOWMAN,BT & SANS,WW (1983)
Experimental logP	4.09	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d204 1.25	DFC
Refractive Index	n20D 1.5698	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-004i-7970000000-bc43a51c3e0e0f2a8537	Spectrum
GC-MS	Fenthion, non-derivatized, GC-MS Spectrum	splash10-00os-4930000000-d917f6fe7c279d0326ef	Spectrum
GC-MS	Fenthion, non-derivatized, GC-MS Spectrum	splash10-00os-4930000000-d917f6fe7c279d0326ef	Spectrum
Predicted GC-MS	Fenthion, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ik9-1970000000-38f4eb65b0f142b27c42	Spectrum
Predicted GC-MS	Fenthion, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Fenthion, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0090000000-cfc6cc7271f15039d91e	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014j-0940000000-4c4cfaec8b9d90f02220	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0gb9-0910000000-30762456be8c99676446	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0gi0-0900000000-fc2e0d1f56a644607b35	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0g4i-0900000000-89a0ce8c9a4d4a49d57c	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0290000000-9da11dc2725fc111b8c4	Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0940000000-199b003861522f4b62e1	Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0gb9-0910000000-14a50b7ed49de35229bc	Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0gi0-0900000000-fc2e0d1f56a644607b35	Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0g4i-0900000000-daf8e3082dcd599a9ef6	Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0g4i-0900000000-677923a06bbdab3e4faa	Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0v4i-0910000000-d74e5478dcae4fb77f71	Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0g4i-0900000000-c7ed3dac5d73de1abfe2	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-0290000000-c4282f269db3a3c433b7	Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0940000000-49b2bd577f2239e1eeed	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-03e61a06874c5e65189c	Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0g4i-0900000000-89a0ce8c9a4d4a49d57c	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0190000000-74fefa9007324dd9847e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002r-1970000000-6492e585fe189b3d02a0	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01pc-9880000000-8949ee35385684bf0416	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-005c-0290000000-b55d858a805aaba2db82	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-0290000000-6e342595466184c4595b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-2900000000-eb2a165616e3235fce1d	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0190000000-953bec3de0724b9038a4	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004u-4790000000-c6f5d3f2adc0c2093b0b	Spectrum