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Showing metabocard for Diazinon (HMDB0032943)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:48 UTC
Update Date2018-03-12 21:55:14 UTC
HMDB IDHMDB0032943
Secondary Accession Numbers
  • HMDB32943
Metabolite Identification
Common NameDiazinon
DescriptionDiazinon, also known as dimpylate or bazudine, belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom. Diazinon exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, diazinon is primarily located in the membrane (predicted from logP). Diazinon can be biosynthesized from 2-isopropyl-6-methylpyrimidin-4-ol. Diazinon is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
DimpylateChEBI
O,O-Diethyl 2-isopropyl-4-methylpyrimidyl-6-thiophosphateChEBI
O,O-Diethyl O-(2-isopropyl-4-methyl-6-pyrimidyl) thionophosphateChEBI
O,O-Diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl) phosphorothioateChEBI
O,O-Diethyl O-[6-methyl-2-(1-methylethyl)pyrimidin-4-yl] thiophosphateChEBI
Phosphorothioic acid, O,O-diethyl O-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) esterChEBI
Dimpylic acidGenerator
O,O-Diethyl 2-isopropyl-4-methylpyrimidyl-6-thiophosphoric acidGenerator
O,O-Diethyl O-(2-isopropyl-4-methyl-6-pyrimidyl) thionophosphoric acidGenerator
O,O-Diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl) phosphorothioic acidGenerator
O,O-Diethyl O-[6-methyl-2-(1-methylethyl)pyrimidin-4-yl] thiophosphoric acidGenerator
Phosphorothioate, O,O-diethyl O-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) esterGenerator
Agridin 60HMDB
Alfa-toxHMDB
AntigalHMDB
AntlakHMDB
BassadinonHMDB
BasudinHMDB
BazudenHMDB
BazudinHMDB
BazudineHMDB
CiazinonHMDB
CompassHMDB
DacutoxHMDB
DassitoxHMDB
DazzelHMDB
DelzinonHMDB
DiagranHMDB
DianonHMDB
DiazideHMDB
DiazinoneHMDB
DiazitolHMDB
DiazolHMDB
DicidHMDB
Diethyl 2-isopropyl-4-methyl-6-pyrimidyl thionophosphateHMDB
Diethyl dimpylatumHMDB
Dimpylate, innHMDB
DipofeneHMDB
DisonexHMDB
DizictolHMDB
DiziktolHMDB
DizinilHMDB
DizinonHMDB
DrawizonHMDB
DyzolHMDB
EktobandHMDB
ExodinHMDB
FezudinHMDB
FlytrolHMDB
GalesanHMDB
GardentoxHMDB
Isopropylmethylpyrimidyl diethyl thiophosphateHMDB
KayazinonHMDB
KayazolHMDB
Knox-outHMDB
MeodinonHMDB
NedcidolHMDB
NeocidolHMDB
NeodinonHMDB
NeotsidolHMDB
NipsanHMDB
NucidolHMDB
OleodiazinonHMDB
OptimizerHMDB
Root guardHMDB
SarolexHMDB
SpectracideHMDB
SpertacideHMDB
SrolexHMDB
TerminatorHMDB
Chemical FormulaC12H21N2O3PS
Average Molecular Weight304.346
Monoisotopic Molecular Weight304.10104975
IUPAC NameO,O-diethyl O-6-methyl-2-(propan-2-yl)pyrimidin-4-yl phosphorothioate
Traditional NameO,O-diethyl O-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate
CAS Registry Number333-41-5
SMILES
CCOP(=S)(OCC)OC1=NC(=NC(C)=C1)C(C)C
InChI Identifier
InChI=1S/C12H21N2O3PS/c1-6-15-18(19,16-7-2)17-11-8-10(5)13-12(14-11)9(3)4/h8-9H,6-7H2,1-5H3
InChI KeyFHIVAFMUCKRCQO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
Sub ClassThiophosphoric acid esters
Direct ParentPyrimidinyl phosphorothioates
Alternative Parents
Substituents
  • Pyrimidinyl phosphorothioate
  • Thiophosphate triester
  • Pyrimidine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Environmental role:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.04 mg/mL at 25 °CNot Available
LogP3.81Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.035 g/LALOGPS
logP4.45ALOGPS
logP4.19ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)4.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area53.47 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity80.76 m³·mol⁻¹ChemAxon
Polarizability31.48 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ufr-3931000000-a70584cb463b92093849View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ufr-3931000000-a70584cb463b92093849View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g1-2390000000-64dc2c6900828222f0d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0009000000-d239df985b8529964c59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ldi-0915000000-ced91e8448a6f8b1969dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gb9-0900000000-48faf44580abfbba15e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gb9-0900000000-109fa8436bb829f5f481View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gb9-0900000000-49a403503b8e1237dddcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0gb9-0900000000-373a091bd4e337f273acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0009000000-25cf20e874bc51155b11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0pvi-0905000000-89807ca393822677be3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0gb9-0900000000-95716b221cd9e83e7d05View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0gb9-1900000000-3772ba2a27f51803e58aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0uxs-4900000000-ce1c6d19b36209036e3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0w2a-6900000000-8011c485731c42bd49f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0009000000-e92acd83cf908233bd11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0aor-0905000000-54dc7dc28ca7ec93789eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0gb9-0900000000-cf4033176e3d7c36c589View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0gb9-1900000000-cb95f2a89d6871b4c0f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0uxs-3900000000-8d43918e6bdf5a791827View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0w2a-7900000000-37289512a80be0d06b70View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0gb9-0900000000-c242d24704a15f911a56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2398000000-292315df845ad237142aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002k-2490000000-b8c16809eaddcd92f2fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ko-9410000000-169637cf10237dcb2a0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-0694000000-cdcbf19ad7bf249fbdb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fs-0890000000-0b16a5fb1c0467d0de87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-0980000000-0e6aa8e81cb45755aac9View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0fbi-7920000000-dce70eb9e413a5f2e1a2View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010928
KNApSAcK IDNot Available
Chemspider ID2909
KEGG Compound IDC14324
BioCyc IDCPD-8965
BiGG IDNot Available
Wikipedia LinkDiazinon
METLIN IDNot Available
PubChem Compound3017
PDB IDNot Available
ChEBI ID34682
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rush T, Liu XQ, Hjelmhaug J, Lobner D: Mechanisms of chlorpyrifos and diazinon induced neurotoxicity in cortical culture. Neuroscience. 2010 Mar 31;166(3):899-906. doi: 10.1016/j.neuroscience.2010.01.025. Epub 2010 Jan 20. [PubMed:20096330 ]
  2. Coleman WE, Tardiff RG: Contaminant levels in animal feeds used for toxicity studies. Arch Environ Contam Toxicol. 1979;8(6):693-702. [PubMed:119496 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .