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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:44:16 UTC
Update Date2017-12-07 04:29:12 UTC
HMDB IDHMDB0041856
Secondary Accession Numbers
  • HMDB41856
Metabolite Identification
Common NameChlorpyrifos
DescriptionA study of the effects of chlorpyrifos on humans exposed over time showed that people exposed to high levels have autoimmune antibodies that are common in people with autoimmune disorders. There is a strong correlation to chronic illness associated with autoimmune disorders after exposure to chlorpyrifos. Among 50 farm pesticides studied, chlorpyrifos was one of two found to be associated with higher risks of lung cancer among frequent pesticide applicators than among infrequent or non-users. Pesticide applicators as a whole were found to have a 50% lower cancer risk than the general public, which is attributable to the nearly 50% lower smoking rate found among farm workers. However, applicators of chlorpyrifos had a 15% lower cancer risk than the general public, which the study suggests indicates a likely link between chlorpyrifos application and lung cancer. Chlorpyrifos (IUPAC name: O,O-diethyl O-3,5,6-trichloropyridin-2-yl phosphorothioate) is a crystalline organophosphate insecticide. It was introduced in 1965 by Dow Chemical Company and is known by many trade names (see table), including Dursban and Lorsban. It acts on the nervous system of insects by inhibiting acetylcholinesterase. Chlorpyrifos is an organophosphate, with potential for both acute toxicity at larger amounts and neurological effects in fetuses and children even at very small amounts. For acute effects, the EPA classifies chlorpyrifos as Class II: moderately toxic. The oral LD50 for chlorpyrifos in experimental animals is 32 to 1000 mg/kg. The dermal LD50 in rats is greater than 2000 mg/kg and 1000 to 2000 mg/kg in rabbits. The 4-hour inhalation LC50 for chlorpyrifos in rats is greater than 200 mg/m3. First registered in 1965 and marketed by Dow Chemical under the tradenames Dursban, Lorsban and Renoban, chlorpyrifos was a well known home and garden insecticide, and at one time it was one of the most widely used household pesticides in the US.
Structure
Thumb
Synonyms
ValueSource
Chlorpyrifos-ethylChEBI
ChlorpyriphosChEBI
m-ChlorpyrifosChEBI
O,O-Diethyl O-(3,5,6-trichloropyridin-2-yl) thiophosphateChEBI
O,O-Diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioateChEBI
Phosphorothioic acid, O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) esterChEBI
TrichlorpyrphosChEBI
O,O-Diethyl O-(3,5,6-trichloropyridin-2-yl) thiophosphoric acidGenerator
O,O-Diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioic acidGenerator
Phosphorothioate, O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) esterGenerator
BonidelHMDB
BrodanHMDB
ChloropyrifosHMDB
ChloropyriphosHMDB
Chlorpyriphos-ethylHMDB
ChlorpyrofosHMDB
ChlorpyrophosHMDB
CorobanHMDB
DanusbanHMDB
Detmol u.a.HMDB
dowco 179HMDB
DurmetHMDB
DursbanHMDB
Dursban 10CRHMDB
Dursban 2EHMDB
Dursban 4EHMDB
Dursban FHMDB
Dursban RHMDB
Empire 20HMDB
EquityHMDB
Ethyl chlorpyriphosHMDB
GeodinfosHMDB
KillmasterHMDB
LentrekHMDB
Lock-ONHMDB
LorsbanHMDB
O,O-Diaethyl-O-3,5,6-trichlor-2-pyridylmonothiophosphatHMDB
O,O-Diethyl O-(3,5,6-trichloro-2-pyridinyl)phosphorothioateHMDB
O,O-Diethyl O-(3,5,6-trichloro-2-pyridyl) phosphorothioateHMDB
O,O-Diethyl O-(3,5,6-trichloropyridin-2-yl) phosphorothioateHMDB
PageantHMDB
PiridaneHMDB
PyrinexHMDB
RadarHMDB
SilrifosHMDB
SpannitHMDB
StipendHMDB
SuSConHMDB
Suscon blueHMDB
Suscon greenHMDB
TafabanHMDB
TerialHMDB
ZidilHMDB
Chemical FormulaC9H11Cl3NO3PS
Average Molecular Weight350.586
Monoisotopic Molecular Weight348.926283546
IUPAC NameO,O-diethyl O-3,5,6-trichloropyridin-2-yl phosphorothioate
Traditional NameO,O-diethyl O-3,5,6-trichloropyridin-2-yl phosphorothioate
CAS Registry Number2921-88-2
SMILES
CCOP(=S)(OCC)OC1=C(Cl)C=C(Cl)C(Cl)=N1
InChI Identifier
InChI=1S/C9H11Cl3NO3PS/c1-3-14-17(18,15-4-2)16-9-7(11)5-6(10)8(12)13-9/h5H,3-4H2,1-2H3
InChI KeySBPBAQFWLVIOKP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as aryl thiophosphates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where at least one R-group is an aryl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassOrganic thiophosphoric acids and derivatives
Direct ParentAryl thiophosphates
Alternative Parents
Substituents
  • Aryl thiophosphate
  • Thiophosphate triester
  • Polyhalopyridine
  • 2-halopyridine
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Route of exposure:

  Parenteral:

  Enteral:

Role

Biological role:

Indirect biological role:

Environmental role:

Physiological effect

Health effect:

  Health condition:

    Psychiatric disorders:

    Gastrointestinal disorders:

    Nervous system disorders:

    General disorders and administration site conditions:

    Musculoskeletal and connective tissue disorders:

    Metabolism and nutrition disorders:

    Vascular disorders:

    Eye disorders:

  Observation:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point42 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0011 mg/mL at 24 °CNot Available
LogP4.96Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
logP5.15ALOGPS
logP4.78ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.58 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity79 m³·mol⁻¹ChemAxon
Polarizability30.4 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)splash10-0002-2793000000-24fe8c73aae05cb109a6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-2794000000-df67df73c4dd26908db1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02vv-4879000000-9255cc8373a5b6df3d65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0119000000-40638c6cc56c702af00fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0309000000-1c03b781190605e158abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-1920000000-1f0cc45d40a433cd21dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ot-2910000000-ae08635e79dc0112ef17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ot-2910000000-b384378ff2454771bc14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ot-2900000000-3169dbfdf2b277cfa7c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-08fs-2900000000-b9485df818d11c39fef7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0309000000-e0f5343f2722d612251fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-1910000000-bfd22e25d1af7f7accb3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ot-2910000000-ba821b94f503bfeb9235View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ot-2900000000-9bb1451e70826e7e9a9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ot-2900000000-9ce44e25c83ae56e97f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-08fs-2900000000-b3d73af1ad2b48fb311bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0119000000-ba99c1365306cb006059View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-006t-0916000000-e5066adbf2b26421940aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ot-0912000000-574ee0c0da4a9208c364View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-0019000000-a09b1f8553c2f9ff157eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-2198000000-678ca9f31d75ee655aa0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0574-9831000000-b360760e7ac0a1382d5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fr2-0329000000-1c8dc6df96eaf1f4e279View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00yl-0595000000-04c8a10e9e94fe0b4a81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-0590000000-f8e446946e10066540ebView in MoNA
MSMass Spectrum (Electron Ionization)splash10-002b-8972000000-01227c0965379003bd5cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2629
KEGG Compound IDC14322
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Linkchlorpyrifos
METLIN IDNot Available
PubChem Compound2730
PDB IDNot Available
ChEBI ID34631
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available