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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:47 UTC
HMDB IDHMDB0014910
Secondary Accession Numbers
  • HMDB14910
Metabolite Identification
Common NameMalathion
DescriptionMalathion 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
Data?1582753234
Synonyms
ValueSource
OvideKegg
[(Dimethoxyphosphinothioyl)thio]butanedioic acid diethyl esterHMDB
CarbophosHMDB
Diethyl (dimethoxyphosphinothioylthio)succinateHMDB
KarbofosHMDB
MaldisonHMDB
MercaptothionHMDB
O,O-Dimethyl S-(1,2-bis(ethoxycarbonyl)ethyl)HMDB
O,O-Dimethyl S-(1,2-dicarbethoxyethyl) dithiophosphateHMDB
O,O-Dimethyl S-(1,2-dicarbethoxyethyl)phosphorodithioateHMDB
O,O-Dimethyl S-1,2-di(ethoxycarbamyl)ethylHMDB
O,O-Dimethyldithiophosphate diethylmercaptosuccinateHMDB
[(Dimethoxyphosphinothioyl)thio]butanedioate diethyl esterHMDB
Diethyl (dimethoxyphosphinothioylthio)succinic acidHMDB
O,O-Dimethyl S-(1,2-dicarbethoxyethyl) dithiophosphoric acidHMDB
O,O-Dimethyl S-(1,2-dicarbethoxyethyl)phosphorodithioic acidHMDB
O,O-Dimethyldithiophosphoric acid diethylmercaptosuccinic acidHMDB
CarbofosHMDB
Compound 4049HMDB
Experimental insecticide 4049HMDB
Insecticide no. 4049HMDB
MalathioneHMDB
Mercaptosuccinic acid diethyl esterHMDB
MercaptotionHMDB
MLTHMDB
OleophosphothionHMDB
SadophosHMDB
CythionHMDB
CarbafosHMDB
PriodermHMDB
Chemical FormulaC10H19O6PS2
Average Molecular Weight330.358
Monoisotopic Molecular Weight330.036066232
IUPAC Name1,4-diethyl 2-{[dimethoxy(sulfanylidene)-lambda5-phosphanyl]sulfanyl}butanedioate
Traditional Name1,4-diethyl 2-{[dimethoxy(sulfanylidene)-lambda5-phosphanyl]sulfanyl}butanedioate
CAS Registry Number121-75-5
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 KeyJXSJBGJIGXNWCI-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point2.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.16 g/LNot Available
LogP2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM165.930932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP2.67ALOGPS
logP1.86ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area71.06 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity78.18 m³·mol⁻¹ChemAxon
Polarizability31.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.08131661259
DarkChem[M-H]-169.7731661259
DeepCCS[M+H]+165.19330932474
DeepCCS[M-H]-162.83530932474
DeepCCS[M-2H]-195.99930932474
DeepCCS[M+Na]+171.28630932474
AllCCS[M+H]+165.532859911
AllCCS[M+H-H2O]+163.232859911
AllCCS[M+NH4]+167.632859911
AllCCS[M+Na]+168.232859911
AllCCS[M-H]-166.932859911
AllCCS[M+Na-2H]-167.732859911
AllCCS[M+HCOO]-168.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MalathionCCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC2853.5Standard polar33892256
MalathionCCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC1963.3Standard non polar33892256
MalathionCCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC2058.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Malathion GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6s-5491000000-3592a22f2b1b3d40e7242017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Malathion GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Malathion GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-8900000000-c6bc16fae6e217410d402014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malathion 10V, Positive-QTOFsplash10-0532-0192000000-80a735602f43e69672f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malathion 20V, Positive-QTOFsplash10-052b-5290000000-5faa1d20fccf211cb57f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malathion 40V, Positive-QTOFsplash10-001i-1910000000-a05ceb6094ed350bc4532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malathion 10V, Negative-QTOFsplash10-0faj-1193000000-b338e42eda1d6c05c7bc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malathion 20V, Negative-QTOFsplash10-0006-1091000000-f5d217b3c309d0fbe4b82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malathion 40V, Negative-QTOFsplash10-00fr-2390000000-b3ee35aea6b6f4b408a82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malathion 10V, Positive-QTOFsplash10-00b9-0901000000-8e0175da8dcd3d5c20f62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malathion 20V, Positive-QTOFsplash10-004i-0900000000-1e03cd94309b778f8fd82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malathion 40V, Positive-QTOFsplash10-00b9-2900000000-49adc13defccdec4c8502021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malathion 10V, Negative-QTOFsplash10-00di-0901000000-6de30c8781d1a5a9985a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malathion 20V, Negative-QTOFsplash10-00di-1900000000-5e2663e1be7df3418ce52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malathion 40V, Negative-QTOFsplash10-00di-0900000000-93b6b347a6b79a7090e52021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00772 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00772 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00772
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3864
KEGG Compound IDC07497
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMalathion
METLIN IDNot Available
PubChem Compound4004
PDB IDNot Available
ChEBI ID141474
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot 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 ]
  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 ]
  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 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. 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. [PubMed:16902246 ]
  6. 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. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Ramos ZR, Fortunato JJ, Agostinho FR, Martins MR, Correa M, Schetinger MR, Dal-Pizzol F, Quevedo J: Influence of malathion on acetylcholinesterase activity in rats submitted to a forced swimming test. Neurotox Res. 2006 Jun;9(4):285-90. [PubMed:16782587 ]
  4. Ahmed M, Rocha JB, Mazzanti CM, Morsch AL, Cargnelutti D, Correa M, Loro V, Morsch VM, Schetinger MR: Malathion, carbofuran and paraquat inhibit Bungarus sindanus (krait) venom acetylcholinesterase and human serum butyrylcholinesterase in vitro. Ecotoxicology. 2007 May;16(4):363-9. Epub 2007 Mar 16. [PubMed:17364237 ]
  5. da Silva AP, Meotti FC, Santos AR, Farina M: Lactational exposure to malathion inhibits brain acetylcholinesterase in mice. Neurotoxicology. 2006 Dec;27(6):1101-5. Epub 2006 Apr 28. [PubMed:16716398 ]
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]