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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:44:16 UTC
Update Date2021-10-13 08:37:15 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
Data?1563863708
Synonyms
ValueSource
BoltonChEBI
BrodanChEBI
Chlorpyrifos ethylChEBI
Chlorpyrifos-ethylChEBI
ChlorpyriphosChEBI
CobaltChEBI
DetmolChEBI
Dowco 179ChEBI
DursbanChEBI
EmpireChEBI
EquityChEBI
EradexChEBI
LentrekChEBI
Lock-ONChEBI
LorsbanChEBI
m-ChlorpyrifosChEBI
NufosChEBI
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
PiridaneChEBI
StipendChEBI
TricelChEBI
TrichlorpyrphosChEBI
WarhawkChEBI
ZodiacKegg
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
ChloropyrifosHMDB
ChloropyriphosHMDB
Chlorpyriphos-ethylHMDB
ChlorpyrofosHMDB
ChlorpyrophosHMDB
CorobanHMDB
DanusbanHMDB
Detmol u.a.HMDB
DurmetHMDB
Dursban 10CRHMDB
Dursban 2EHMDB
Dursban 4EHMDB
Dursban FHMDB
Dursban RHMDB
Empire 20HMDB
Ethyl chlorpyriphosHMDB
GeodinfosHMDB
KillmasterHMDB
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
PyrinexHMDB
RadarHMDB
SilrifosHMDB
SpannitHMDB
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 Nameterial
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
Description Belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
Sub ClassThiophosphoric acid esters
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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point42 °CNot Available
Boiling Point375.90 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.0011 mg/mL at 24 °CNot Available
LogP4.96Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available201.738http://allccs.zhulab.cn/database/detail?ID=AllCCS00001306
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
logP10(5.15) g/LALOGPS
logP10(4.78) g/LChemAxon
logS10(-5.4) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChlorpyrifosCCOP(=S)(OCC)OC1=C(Cl)C=C(Cl)C(Cl)=N12803.1Standard polar33892256
ChlorpyrifosCCOP(=S)(OCC)OC1=C(Cl)C=C(Cl)C(Cl)=N11964.9Standard non polar33892256
ChlorpyrifosCCOP(=S)(OCC)OC1=C(Cl)C=C(Cl)C(Cl)=N11961.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Chlorpyrifos EI-B (Non-derivatized)splash10-0002-2793000000-24fe8c73aae05cb109a62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chlorpyrifos EI-B (Non-derivatized)splash10-0002-2794000000-df67df73c4dd26908db12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chlorpyrifos EI-B (Non-derivatized)splash10-0002-2793000000-24fe8c73aae05cb109a62018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chlorpyrifos EI-B (Non-derivatized)splash10-0002-2794000000-df67df73c4dd26908db12018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorpyrifos GC-MS (Non-derivatized) - 70eV, Positivesplash10-02vv-4879000000-9255cc8373a5b6df3d652017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorpyrifos GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-002b-8972000000-01227c0965379003bd5c2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-00di-0119000000-40638c6cc56c702af00f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-0002-0309000000-1c03b781190605e158ab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-0002-1920000000-1f0cc45d40a433cd21db2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-01ot-2910000000-ae08635e79dc0112ef172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-01ot-2910000000-b384378ff2454771bc142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-01ot-2900000000-3169dbfdf2b277cfa7c02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-08fs-2900000000-b9485df818d11c39fef72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-0002-0309000000-e0f5343f2722d612251f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-0002-1910000000-bfd22e25d1af7f7accb32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-01ot-2910000000-ba821b94f503bfeb92352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-01ot-2900000000-9bb1451e70826e7e9a9f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-01ot-2900000000-9ce44e25c83ae56e97f02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-08fs-2900000000-b3d73af1ad2b48fb311b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOFsplash10-00di-0119000000-ba99c1365306cb0060592017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos ESI-ITFT , positive-QTOFsplash10-006t-0916000000-e5066adbf2b26421940a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos LC-ESI-QFT , positive-QTOFsplash10-01ot-0912000000-574ee0c0da4a9208c3642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos 35V, Positive-QTOFsplash10-00di-0119000000-9c6de680a79a370a94482021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos 35V, Positive-QTOFsplash10-00di-0019000000-8f591ca38c38b7d4aefe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpyrifos 60V, Positive-QTOFsplash10-01ot-2900000000-f12e60a6223e79be2b2f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpyrifos 10V, Positive-QTOFsplash10-006t-0019000000-a09b1f8553c2f9ff157e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpyrifos 20V, Positive-QTOFsplash10-006x-2198000000-678ca9f31d75ee655aa02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpyrifos 40V, Positive-QTOFsplash10-0574-9831000000-b360760e7ac0a1382d5e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpyrifos 10V, Negative-QTOFsplash10-0fr2-0329000000-1c8dc6df96eaf1f4e2792016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpyrifos 20V, Negative-QTOFsplash10-00yl-0595000000-04c8a10e9e94fe0b4a812016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpyrifos 40V, Negative-QTOFsplash10-000f-0590000000-f8e446946e10066540eb2016-08-04Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1347681
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available