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
CHEBI:34631
CAS Number
2921-88-2
TTD ID
D0M5ES
INTEDE ID
DR2271

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
2-aminomuconic semialdehyde dehydrogenase (ALDH8A1) OTINY3MW AL8A1_HUMAN Gene/Protein Processing [3]
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [4]
Acetylcholinesterase (ACHE) OT2H8HG6 ACES_HUMAN Gene/Protein Processing [5]
Androgen receptor (AR) OTUBKAZZ ANDR_HUMAN Gene/Protein Processing [6]
Androgen-induced gene 1 protein (AIG1) OTJB2UTH AIG1_HUMAN Drug Response [7]
Annexin A10 (ANXA10) OTA8LWSL ANX10_HUMAN Gene/Protein Processing [8]
Annexin A5 (ANXA5) OTZS877V ANXA5_HUMAN Protein Interaction/Cellular Processes [9]
Apolipoprotein E (APOE) OTFOWL2H APOE_HUMAN Drug Response [10]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [11]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [12]
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 Successful validation of genomic biomarkers for human immunotoxicity in Jurkat T cells in vitro. J Appl Toxicol. 2015 Jul;35(7):831-41.
4 Chlorpyrifos subthreshold exposure induces epithelial-mesenchymal transition in breast cancer cells. Ecotoxicol Environ Saf. 2020 Dec 1;205:111312. doi: 10.1016/j.ecoenv.2020.111312. Epub 2020 Sep 18.
5 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.
6 Comparison of the Toxicological Effects of Pesticides in Non-Tumorigenic MCF-12A and Tumorigenic MCF-7 Human Breast Cells. Int J Environ Res Public Health. 2022 Apr 7;19(8):4453. doi: 10.3390/ijerph19084453.
7 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.
8 RNA-protein correlation of liver toxicity markers in HepaRG cells. EXCLI J. 2020 Jan 17;19:135-153. doi: 10.17179/excli2019-2005. eCollection 2020.
9 Rosiglitazone inhibits chlorpyrifos-induced apoptosis via modulation of the oxidative stress and inflammatory response in SH-SY5Y cells. Toxicol Appl Pharmacol. 2014 Jul 15;278(2):159-71.
10 Exposure to chlorpyrifos at different ages triggers APOE genotype-specific responses in social behavior, body weight and hypothalamic gene expression. Environ Res. 2019 Nov;178:108684. doi: 10.1016/j.envres.2019.108684. Epub 2019 Aug 23.
11 Aryl-phosphorus-containing flame retardants induce oxidative stress, the p53-dependent DNA damage response and mitochondrial impairment in A549?cells. Environ Pollut. 2019 Jul;250:58-67. doi: 10.1016/j.envpol.2019.03.109. Epub 2019 Apr 4.
12 Characterization of chlorpyrifos-induced apoptosis in placental cells. Toxicology. 2008 Feb 28;244(2-3):98-110. doi: 10.1016/j.tox.2007.10.020. Epub 2007 Oct 30.