ContaminantDB: Malathion (MDCA)

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-06-03 10:07:26 UTC

Update Date

2016-11-09 01:22:47 UTC

Accession Number

CHEM042716

Identification

Common Name

Malathion (MDCA)

Class

Small Molecule

Description

Malathion dicarboxylic acid is a metabolite of malathion. Malathion is an organophosphate parasympathomimetic which binds irreversibly to cholinesterase. Malathion is an insecticide of relatively low human toxicity; however, a 2010 study has shown that children with higher levels of organophosphate pesticide metabolites in their urine are more likely to have attention deficit hyperactivity disorder. In the former USSR it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion. (Wikipedia)

Contaminant Sources

STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Malathion dicarboxylate	Generator
Lamivudine-triphosphoric acid	HMDB

Chemical Formula

C₆H₁₁O₆PS₂

Average Molecular Mass

274.252 g/mol

Monoisotopic Mass

273.973 g/mol

CAS Registry Number

1190-28-9

IUPAC Name

2-{[dimethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}butanedioic acid

Traditional Name

2-{[dimethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}butanedioic acid

SMILES

COP(=S)(OC)SC(CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C6H11O6PS2/c1-11-13(14,12-2)15-4(6(9)10)3-5(7)8/h4H,3H2,1-2H3,(H,7,8)(H,9,10)

InChI Key

NIUNKPWHNGMQRE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Thia fatty acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.08 g/L	ALOGPS
logP	0.84	ALOGPS
logP	0.85	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	59.15 m³·mol⁻¹	ChemAxon
Polarizability	23.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05xu-5890000000-6557719b56fb3f44f0d3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0fmr-9345200000-ad5c09316784677c4f3c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0m0t-0890000000-e76529c960e5b33592bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9260000000-4c31a18aea9cead77bd2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-1900000000-e83cc21cc62be4fb516e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0190000000-fbb20cdfeb3fabf724aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0490000000-d497185002b89ac81270	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03mj-0930000000-23755c1cd50f527765af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-8fb73d917ddfc54af701	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-70a3a236d1db41ba4fbe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0900000000-d5ecd73eeb5bfe9c05eb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-5de3ae3c049e46a76372	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1900000000-408b7921d5d5e4b6bcee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1900000000-bd720cdebbd03a6ccb03	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0060636

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

13827

ChEBI ID

Not Available

PubChem Compound ID

75607486

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.

2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.

3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.

4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.

5. The lipid handbook with CD-ROM

Malathion (MDCA) (CHEM042716)

Structure for CHEM042716: Malathion (MDCA)