Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2271)
Drug Name
Chlorpyrifos
Synonyms
Bonidel; Brodan; Chloropyrifos; Chlorpyrifos (Dursban); Chlorpyrifos-ethyl; Chlorpyriphos; Chlorpyriphos-ethyl; Clorpyrifos; Coroban; Danusban; Detmol U.A.; Detmol ua; Dhanusban; Dowco 179; Durmet; Dursban; Dursban 10CR; Dursban 4E; Dursban F; Dursban R; Equity; Ethyl chlorpyriphos; Geodinfos; Killmaster; Lentrek; Lock-On; Lorsban; Piridane; Pyrinex; Spannit; Stipend; Suscon blue; Suscon green; Tafaban; Terial; Trichlorpyrphos; chlorpyrifos; suSCon; 2921-88-2; Grofo; Phosphorothioic acid, O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) ester; Zidil
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 350.6 Topological Polar Surface Area 72.7
Heavy Atom Count 18 Rotatable Bond Count 6
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
2730
ChEBI ID
CHEBI:34631
CAS Number
2921-88-2
TTD Drug ID
D0M5ES
Formula
C9H11Cl3NO3PS
Canonical SMILES
CCOP(=S)(OCC)OC1=NC(=C(C=C1Cl)Cl)Cl
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
InChIKey
SBPBAQFWLVIOKP-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
3,5,6-trichloro-2-pyridinol DM005851
23017
Unclear 1 [3] , [4] , [3]
Chlorpyrifos-oxon DM005850
21804
Unclear 1 [5] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006256 Chlorpyrifos Chlorpyrifos-oxon Unclear Unclear [5], [4]
MR006257 Chlorpyrifos 3,5,6-trichloro-2-pyridinol Unclear Unclear [3], [4], [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 BM3 (cypBM3) DME1236 Bacillus megaterium
M9TKI6_BACME
1.14.14.1
[2]
References
1 PubChem 2019 update: improved access to chemical data. Nucleic Acids Res. 2019 Jan 8; 47(D1):D1102-1109. (PubChem CID: 65841)
2 PEGylation of cytochrome P450 enhances its biocatalytic performance for pesticide transformation. Int J Biol Macromol. 2017 Dec;105(Pt 1):163-170.
3 Determination of chlorpyrifos and its metabolites in cells and culture media by liquid chromatography-electrospray ionization tandem mass spectrometry
4 Direct determination of chlorpyrifos and its main metabolite 3,5, 6-trichloro-2-pyridinol in human serum and urine by coupled-column liquid chromatography/electrospray-tandem mass spectrometry
5 Determination of chlorpyrifos and its metabolites in rat brain tissue using coupled-column liquid chromatography/electrospray ionization tandem mass spectrometry

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