Details of the Drug

General Information of Drug (ID: DMKPUI6)

Drug Name
CHLORPYRIFOS
Synonyms
chlorpyrifos; 2921-88-2; Chlorpyriphos; Dursban; Trichlorpyrphos; Lorsban; Chlorpyrifos-ethyl; Pyrinex; Coroban; Brodan; Killmaster; Piridane; Danusban; Spannit; Lentrek; Geodinfos; Tafaban; Stipend; Bonidel; Zidil; Terial; Durmet; Equity; Suscon green; Suscon blue; suSCon; Dursban R; Dursban F; Lock-On; Dursban 4E; Dowco 179; Chlorpyriphos-ethyl; Ethyl chlorpyriphos; Dursban 10CR; Chlorpyrifos (Dursban); Detmol U.A.; Phosphorothioic acid, O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) ester; Chloropyrifos; Clorpyrifos; Dhanusban; Grofo; Detmol ua
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 350.6
Logarithm of the Partition Coefficient (xlogp) 5.3
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C9H11Cl3NO3PS
IUPAC Name
diethoxy-sulfanylidene-(3,5,6-trichloropyridin-2-yl)oxy-lambda5-phosphane
Canonical SMILES
CCOP(=S)(OCC)OC1=NC(=C(C=C1Cl)Cl)Cl
InChI
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
Cross-matching ID
PubChem CID
2730
ChEBI ID
CHEMBL34631
CAS Number
2921-88-2
TTD ID
D0M5ES
INTEDE ID
DR2271
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Acetylcholinesterase (AChE) TT1RS9F ACES_HUMAN Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 BM3 (cypBM3)
Main DME 		DEMQRS9 M9TKI6_BACME Substrate [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Androgen-induced gene 1 protein (AIG1) OTJB2UTH AIG1_HUMAN Drug Response [3]
Apoptosis-associated speck-like protein containing a CARD (PYCARD) OT67RON3 ASC_HUMAN Gene/Protein Processing [4]
Apoptosis-inducing factor 1, mitochondrial (AIFM1) OTKPWB7Q AIFM1_HUMAN Gene/Protein Processing [5]
Apoptotic protease-activating factor 1 (APAF1) OTJWIVY0 APAF_HUMAN Gene/Protein Processing [4]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [6]
Bcl-2-interacting killer (BIK) OTTH1T3D BIK_HUMAN Drug Response [3]
Bcl2-associated agonist of cell death (BAD) OT63ERYM BAD_HUMAN Gene/Protein Processing [4]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [7]
CAP-Gly domain-containing linker protein 3 (CLIP3) OTGJEGIB CLIP3_HUMAN Gene/Protein Processing [8]
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Acetylcholinesterase (AChE) DTT ACHE 6.39E-02 -1.07 -1.15
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Synthesis of the novel series of bispyridinium compounds bearing (E)-but-2-ene linker and evaluation of their reactivation activity against chlorpy... Bioorg Med Chem Lett. 2006 Feb;16(3):622-7.
2 PEGylation of cytochrome P450 enhances its biocatalytic performance for pesticide transformation. Int J Biol Macromol. 2017 Dec;105(Pt 1):163-170.
3 Application of human haploid cell genetic screening model in identifying the genes required for resistance to environmental toxicants: Chlorpyrifos as a case study. J Pharmacol Toxicol Methods. 2015 Nov-Dec;76:76-82. doi: 10.1016/j.vascn.2015.08.154. Epub 2015 Aug 20.
4 Chlorpyrifos induces NLRP3 inflammasome and pyroptosis/apoptosis via mitochondrial oxidative stress in human keratinocyte HaCaT cells. Toxicology. 2015 Dec 2;338:37-46. doi: 10.1016/j.tox.2015.09.006. Epub 2015 Oct 3.
5 Organophosphate-pesticides induced survival mechanisms and APE1-mediated Nrf2 regulation in non-small-cell lung cancer cells. J Biochem Mol Toxicol. 2021 Feb;35(2):e22640. doi: 10.1002/jbt.22640. Epub 2020 Oct 20.
6 Impact of chlorpyrifos on human villous trophoblasts and chorionic villi. Toxicol Appl Pharmacol. 2017 Aug 15;329:26-39. doi: 10.1016/j.taap.2017.05.026. Epub 2017 May 23.
7 Chlorpyrifos modifies the expression of genes involved in human placental function. Reprod Toxicol. 2012 Jun;33(3):331-8. doi: 10.1016/j.reprotox.2012.01.003. Epub 2012 Jan 21.
8 The common insecticides cyfluthrin and chlorpyrifos alter the expression of a subset of genes with diverse functions in primary human astrocytes. Toxicol Sci. 2006 Sep;93(1):125-35. doi: 10.1093/toxsci/kfl046. Epub 2006 Jun 21.
9 Chlorpyrifos induces cell proliferation in MCF-7 and MDA-MB-231?cells, through cholinergic and Wnt/-catenin signaling disruption, AChE-R upregulation and oxidative stress generation after single and repeated treatment. Food Chem Toxicol. 2021 Jun;152:112241. doi: 10.1016/j.fct.2021.112241. Epub 2021 Apr 27.