Human Metabolome Database: Showing metabocard for Chlorpyrifos (HMDB0041856)

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Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:44:16 UTC

Update Date

2019-07-23 06:35:08 UTC

HMDB ID

HMDB0041856

Secondary Accession Numbers

HMDB41856

Metabolite Identification

Common Name

Chlorpyrifos

Description

A 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Bolton	ChEBI
Brodan	ChEBI
Chlorpyrifos-ethyl	ChEBI
Chlorpyriphos	ChEBI
Cobalt	ChEBI
Detmol	ChEBI
Dowco 179	ChEBI
Dursban	ChEBI
Empire	ChEBI
Equity	ChEBI
Eradex	ChEBI
Lentrek	ChEBI
Lock-ON	ChEBI
Lorsban	ChEBI
m-Chlorpyrifos	ChEBI
Nufos	ChEBI
O,O-Diethyl O-(3,5,6-trichloropyridin-2-yl) thiophosphate	ChEBI
O,O-Diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioate	ChEBI
Phosphorothioic acid, O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) ester	ChEBI
Piridane	ChEBI
Stipend	ChEBI
Tricel	ChEBI
Trichlorpyrphos	ChEBI
Warhawk	ChEBI
Zodiac	Kegg
O,O-Diethyl O-(3,5,6-trichloropyridin-2-yl) thiophosphoric acid	Generator
O,O-Diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioic acid	Generator
Phosphorothioate, O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) ester	Generator
Bonidel	HMDB
Chloropyrifos	HMDB
Chloropyriphos	HMDB
Chlorpyriphos-ethyl	HMDB
Chlorpyrofos	HMDB
Chlorpyrophos	HMDB
Coroban	HMDB
Danusban	HMDB
Detmol u.a.	HMDB
Durmet	HMDB
Dursban 10CR	HMDB
Dursban 2E	HMDB
Dursban 4E	HMDB
Dursban F	HMDB
Dursban R	HMDB
Empire 20	HMDB
Ethyl chlorpyriphos	HMDB
Geodinfos	HMDB
Killmaster	HMDB
O,O-Diaethyl-O-3,5,6-trichlor-2-pyridylmonothiophosphat	HMDB
O,O-Diethyl O-(3,5,6-trichloro-2-pyridinyl)phosphorothioate	HMDB
O,O-Diethyl O-(3,5,6-trichloro-2-pyridyl) phosphorothioate	HMDB
O,O-Diethyl O-(3,5,6-trichloropyridin-2-yl) phosphorothioate	HMDB
Pageant	HMDB
Pyrinex	HMDB
Radar	HMDB
Silrifos	HMDB
Spannit	HMDB
SuSCon	HMDB
Suscon blue	HMDB
Suscon green	HMDB
Tafaban	HMDB
Terial	HMDB
Zidil	HMDB

Chemical Formula

C₉H₁₁Cl₃NO₃PS

Average Molecular Weight

350.586

Monoisotopic Molecular Weight

348.926283546

IUPAC Name

O,O-diethyl O-3,5,6-trichloropyridin-2-yl phosphorothioate

Traditional Name

terial

CAS Registry Number

2921-88-2

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 Key

SBPBAQFWLVIOKP-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic thiophosphoric acids and derivatives

Sub Class

Thiophosphoric acid esters

Direct Parent

Aryl 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

organic thiophosphate (CHEBI:34631 )
chloropyridine (CHEBI:34631 )
Organophosphorus insecticides (C14322 )
a small molecule (CPD-8963 )

Ontology

Synthetic

Route of exposure:

Parenteral:

Enteral:

Ingestion

Nutrient

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	42 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0011 mg/mL at 24 °C	Not Available
LogP	4.96	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0014 g/L	ALOGPS
logP	5.15	ALOGPS
logP	4.78	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.58 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	79 m³·mol⁻¹	ChemAxon
Polarizability	30.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-2793000000-24fe8c73aae05cb109a6	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-2794000000-df67df73c4dd26908db1	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-2793000000-24fe8c73aae05cb109a6	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-2794000000-df67df73c4dd26908db1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-02vv-4879000000-9255cc8373a5b6df3d65	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-0119000000-40638c6cc56c702af00f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0309000000-1c03b781190605e158ab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-1920000000-1f0cc45d40a433cd21db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-01ot-2910000000-ae08635e79dc0112ef17	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-01ot-2910000000-b384378ff2454771bc14	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-01ot-2900000000-3169dbfdf2b277cfa7c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-08fs-2900000000-b9485df818d11c39fef7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0309000000-e0f5343f2722d612251f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-1910000000-bfd22e25d1af7f7accb3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-01ot-2910000000-ba821b94f503bfeb9235	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-01ot-2900000000-9bb1451e70826e7e9a9f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-01ot-2900000000-9ce44e25c83ae56e97f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-08fs-2900000000-b3d73af1ad2b48fb311b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-0119000000-ba99c1365306cb006059	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-006t-0916000000-e5066adbf2b26421940a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-01ot-0912000000-574ee0c0da4a9208c364	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006t-0019000000-a09b1f8553c2f9ff157e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-2198000000-678ca9f31d75ee655aa0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0574-9831000000-b360760e7ac0a1382d5e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fr2-0329000000-1c8dc6df96eaf1f4e279	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00yl-0595000000-04c8a10e9e94fe0b4a81	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-0590000000-f8e446946e10066540eb	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002b-8972000000-01227c0965379003bd5c	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2629

KEGG Compound ID

C14322

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorpyrifos

METLIN ID

Not Available

PubChem Compound

2730

PDB ID

Not Available

ChEBI ID

34631

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Chlorpyrifos (HMDB0041856)

Structure for HMDB0041856 (Chlorpyrifos)