Human Metabolome Database Version 3.5

Showing metabocard for Malathion (HMDB14910)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:50 -0600
Update Date 2013-02-08 17:32:34 -0700
HMDB ID HMDB14910
Secondary Accession Numbers None
Metabolite Identification
Common Name Malathion
Description 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 Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Carbofos
  2. Carbophos
  3. Compound 4049
  4. Experimental insecticide 4049
  5. Insecticide no. 4049
  6. Malathione
  7. Maldison
  8. Mercaptosuccinic acid diethyl ester
  9. Mercaptothion
  10. Mercaptotion
  11. MLT
  12. Oleophosphothion
Chemical Formula C10H19O6PS2
Average Molecular Weight 330.358
Monoisotopic Molecular Weight 330.036066232
IUPAC Name 1,4-diethyl 2-{[dimethoxy(sulfanylidene)-$l^{5}-phosphanyl]sulfanyl}butanedioate
Traditional IUPAC Name malathion
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
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Carboxylic Acids and Derivatives
Sub Class Dicarboxylic Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Fatty Acid Esters
  • Organic Thiophosphoric Acid Esters
  • Organophosphorus insecticides(KEGG)
  • a small molecule(Cyc)
  • carboxyalkyl phosphate(ChEBI)
  • organic thiophosphate(ChEBI)
  • organothiophosphate insecticide(ChEBI)
Substituents
  • Carboxylic Acid Ester
  • Thiophosphonic Acid Derivative
Direct Parent Dicarboxylic Acids and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Cholinesterase Inhibitors
  • Insecticides
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point 2.8 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1.65e-01 g/L Not Available
LogP 2 Not Available
Predicted Properties
Property Value Source
LogP 2.67 ALOGPS
LogP 1.86 ChemAxon
LogS -3.30 ALOGPS
pKa (strongest basic) -6.8 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 71.06 A2 ChemAxon
Rotatable Bond Count 11 ChemAxon
Refractivity 78.18 ChemAxon
Polarizability 31.66 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00772
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00772
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00772 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 3864 Link_out
KEGG Compound ID C07497 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Malathion Link_out
NuGOwiki Link HMDB14910 Link_out
Metagene Link HMDB14910 Link_out
METLIN ID Not Available
PubChem Compound 4004 Link_out
PDB ID Not Available
ChEBI ID 6651 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Baker EL Jr, Warren M, Zack M, Dobbin RD, Miles JW, Miller S, Alderman L, Teeters WR: Epidemic malathion poisoning in Pakistan malaria workers. Lancet. 1978 Jan 7;1(8054):31-4. Pubmed: 74508 Link_out
  2. Edwards JW, Lee SG, Heath LM, Pisaniello DL: Worker exposure and a risk assessment of malathion and fenthion used in the control of Mediterranean fruit fly in South Australia. Environ Res. 2007 Jan;103(1):38-45. Epub 2006 Aug 17. Pubmed: 16914134 Link_out
  3. Bonner MR, Coble J, Blair A, Beane Freeman LE, Hoppin JA, Sandler DP, Alavanja MC: Malathion exposure and the incidence of cancer in the agricultural health study. Am J Epidemiol. 2007 Nov 1;166(9):1023-34. Epub 2007 Aug 23. Pubmed: 17720683 Link_out

Enzymes
Name: Cholinesterase
Reactions: Not Available
Gene Name: BCHE
Uniprot ID: P06276 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2B6
Reactions: Not Available
Gene Name: CYP2B6
Uniprot ID: P20813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA