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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 18:09:07 UTC
Update Date2017-10-23 19:15:45 UTC
HMDB IDHMDB0060626
Secondary Accession Numbers
  • HMDB60626
Metabolite Identification
Common NameMalathion monocarboxylic acid
DescriptionMalathion monocarboxylic 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)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC8H15O6PS2
Average Molecular Weight302.305
Monoisotopic Molecular Weight302.004766104
IUPAC Name3-{[dimethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}-4-ethoxy-4-oxobutanoic acid
Traditional Name3-{[dimethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}-4-ethoxy-4-oxobutanoic acid
CAS Registry NumberNot Available
SMILES
CCOC(=O)C(CC(O)=O)SP(=S)(OC)OC
InChI Identifier
InChI=1S/C8H15O6PS2/c1-4-14-8(11)6(5-7(9)10)17-15(16,12-2)13-3/h6H,4-5H2,1-3H3,(H,9,10)
InChI KeyFARGSBYVTRDSKX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentThia fatty acids
Alternative Parents
Substituents
  • Fatty acid ester
  • Thia fatty acid
  • Dicarboxylic acid or derivatives
  • Dithiophosphate o-ester
  • Dithiophosphate s-ester
  • Organic dithiophosphate
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organothiophosphorus compound
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.67 g/LALOGPS
logP1.5ALOGPS
logP1.35ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.06 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity68.66 m³·mol⁻¹ChemAxon
Polarizability27.38 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-5390000000-9ff17fa6d1f9e705eed5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-8439000000-6544e3c43666a9e9d496View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0h00-0980000000-c01f175385c5970f1ff8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-8390000000-0a4238806b33de860e36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-fbb8b7422f05c896e260View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1092000000-3bb0c9be0da584649d78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r2-4590000000-a27ae2b1b2303130e7f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0592-2950000000-95f1e9dbd4e53cbabdadView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00903
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (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. [PubMed:11413487 ]
      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. [PubMed:16902246 ]
      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. [PubMed:17374880 ]
      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. [PubMed:20044567 ]
      5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.