ChemFOnt: Showing chemical card for Malathion (CFc000009237)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:19 UTC

Chemfont ID

CFc000009237

Molecule Identification

Common Name

Malathion

Definition

Malathion is only found in individuals that have used or taken this drug. It is a wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes. [PubChem]Malathion is a nonsystemic, wide-spectrum organophosphate insecticide. It inhibits acetylcholinesterase activity of most eukaryotes. Malathion is toxic to aquatic organisms, but has a relatively low toxicity for birds and mammals. The major metabolites of malathion are mono- and di-carboxylic acid derivatives, and malaoxon is a minor metabolite. However, it is malaoxon that is the strongest cholinesterase inhibitor. Cholinesterases catalyze the hydrolysis of the neurotransmitter acetylcholine into choline and acetic acid, a reaction necessary to allow a cholinergic neuron to return to its resting state after activation. Because of its essential function, chemicals that interfere with the action of cholinesterase are potent neurotoxins, causing muscle spasms and ultimately death.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ovide	Kegg
[(Dimethoxyphosphinothioyl)thio]butanedioic acid diethyl ester	HMDB
Carbophos	HMDB
Diethyl (dimethoxyphosphinothioylthio)succinate	HMDB
Karbofos	HMDB
Maldison	HMDB
Mercaptothion	HMDB
O,O-Dimethyl S-(1,2-bis(ethoxycarbonyl)ethyl)	HMDB
O,O-Dimethyl S-(1,2-dicarbethoxyethyl) dithiophosphate	HMDB
O,O-Dimethyl S-(1,2-dicarbethoxyethyl)phosphorodithioate	HMDB
O,O-Dimethyl S-1,2-di(ethoxycarbamyl)ethyl	HMDB
O,O-Dimethyldithiophosphate diethylmercaptosuccinate	HMDB
[(Dimethoxyphosphinothioyl)thio]butanedioate diethyl ester	HMDB
Diethyl (dimethoxyphosphinothioylthio)succinic acid	HMDB
O,O-Dimethyl S-(1,2-dicarbethoxyethyl) dithiophosphoric acid	HMDB
O,O-Dimethyl S-(1,2-dicarbethoxyethyl)phosphorodithioic acid	HMDB
O,O-Dimethyldithiophosphoric acid diethylmercaptosuccinic acid	HMDB
Carbofos	HMDB
Compound 4049	HMDB
Experimental insecticide 4049	HMDB
Insecticide no. 4049	HMDB
Malathione	HMDB
Mercaptosuccinic acid diethyl ester	HMDB
Mercaptotion	HMDB
MLT	HMDB
Oleophosphothion	HMDB
Sadophos	HMDB
Cythion	HMDB
Carbafos	HMDB
Prioderm	HMDB

Chemical Formula

C₁₀H₁₉O₆PS₂

Average Molecular Weight

330.358

Monoisotopic Molecular Weight

330.036066232

IUPAC Name

1,4-diethyl 2-{[dimethoxy(sulfanylidene)-lambda5-phosphanyl]sulfanyl}butanedioate

Traditional Name

1,4-diethyl 2-{[dimethoxy(sulfanylidene)-lambda5-phosphanyl]sulfanyl}butanedioate

CAS Registry Number

121-75-5

SMILES

CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC

InChI Identifier

InChI=1S/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(18,13-3)14-4/h8H,5-7H2,1-4H3

InChI Key

JXSJBGJIGXNWCI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Dicarboxylic acid or derivatives
Dithiophosphate o-ester
Dithiophosphate s-ester
Organic dithiophosphate
Carboxylic acid ester
Carboxylic acid derivative
Organothiophosphorus compound
Sulfenyl compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organosulfur compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ethyl ester (CHEBI:6651 )
diester (CHEBI:6651 )
organic thiophosphate (CHEBI:6651 )
carboxyalkyl phosphate (CHEBI:6651 )
Organophosphorus insecticides (C07497 )
a small molecule (CPD-13116 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014910)

Process

Not Available

Role

Industrial application

Agrochemical (HMDB: HMDB0014910)
Pediculicide (HMDB: HMDB0014910)

Pharmaceutical industry

Antimicrobial agent

Scabicide (HMDB: HMDB0014910)

Biological role

Modulator

Inhibitor

EC 3.1.1.8 (cholinesterase) inhibitor (HMDB: HMDB0014910)
EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0014910)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	2.67	ALOGPS
logP	1.86	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	78.18 m³·mol⁻¹	ChemAxon
Polarizability	31.66 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon