Cannabis Compound Database: Showing Compound Card for Fenthion (CDB006254)

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Record Information

Version

1.0

Created at

2020-07-28 20:23:03 UTC

Updated at

2020-12-07 19:12:21 UTC

CannabisDB ID

CDB006254

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Fenthion

Description

Fenthion, also known as MPP or mercaptophos, 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. Based on a literature review a significant number of articles have been published on Fenthion.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₁₀H₁₅O₃PS₂

Average Molecular Weight

278.328

Monoisotopic Molecular Weight

278.020022238

IUPAC Name

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

Traditional Name

fenthion

CAS Registry Number

55-38-9

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 Key

PNVJTZOFSHSLTO-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.

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

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	7.5°C	Not Available
Boiling Point	87 °C (at 0.01 mmHg)	Not Available
Water Solubility	54 ppm (at 20 °C)	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-004i-7970000000-bc43a51c3e0e0f2a8537	2014-09-20	View 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	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014j-0940000000-4c4cfaec8b9d90f02220	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0gb9-0910000000-30762456be8c99676446	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0gi0-0900000000-fc2e0d1f56a644607b35	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0g4i-0900000000-89a0ce8c9a4d4a49d57c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0290000000-9da11dc2725fc111b8c4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0940000000-199b003861522f4b62e1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0gb9-0910000000-14a50b7ed49de35229bc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0gi0-0900000000-fc2e0d1f56a644607b35	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0g4i-0900000000-daf8e3082dcd599a9ef6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0g4i-0900000000-677923a06bbdab3e4faa	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0v4i-0910000000-d74e5478dcae4fb77f71	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0g4i-0900000000-c7ed3dac5d73de1abfe2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-0290000000-c4282f269db3a3c433b7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0940000000-49b2bd577f2239e1eeed	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-03e61a06874c5e65189c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0g4i-0900000000-89a0ce8c9a4d4a49d57c	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0190000000-74fefa9007324dd9847e	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002r-1970000000-6492e585fe189b3d02a0	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01pc-9880000000-8949ee35385684bf0416	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-005c-0290000000-b55d858a805aaba2db82	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-0290000000-6e342595466184c4595b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-2900000000-eb2a165616e3235fce1d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0190000000-953bec3de0724b9038a4	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004u-4790000000-c6f5d3f2adc0c2093b0b	2021-09-23	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.40 MHz, CDCl₃, experimental)		Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0033209

DrugBank ID

DB11412

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011222

KNApSAcK ID

Not Available

Chemspider ID

3229

KEGG Compound ID

C14420

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fenthion

METLIN ID

Not Available

PubChem Compound

3346

PDB ID

Not Available

ChEBI ID

34761

References

General References

Moulins JR, Blais M, Montsion K, Tully J, Mohan W, Gagnon M, McRitchie T, Kwong K, Snider N, Blais DR: Multiresidue Method of Analysis of Pesticides in Medical Cannabis. J AOAC Int. 2018 Nov 1;101(6):1948-1960. doi: 10.5740/jaoacint.17-0495. Epub 2018 May 29. [PubMed:29843862 ]

Showing Compound Card for Fenthion (CDB006254)

Structure for CDB006254 (Fenthion)