Details of the Drug

General Information of Drug (ID: DMGBT68)

Drug Name
Chlorphrifos oxon
Synonyms Diethyl 3,5,6-trichloropyridin-2-yl phosphate
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): 0 Molecular Weight (mw) 334.5
Logarithm of the Partition Coefficient (xlogp) 3.5
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C9H11Cl3NO4P
IUPAC Name
diethyl (3,5,6-trichloropyridin-2-yl) phosphate
Canonical SMILES
CCOP(=O)(OCC)OC1=NC(=C(C=C1Cl)Cl)Cl
InChI
InChI=1S/C9H11Cl3NO4P/c1-3-15-18(14,16-4-2)17-9-7(11)5-6(10)8(12)13-9/h5H,3-4H2,1-2H3
InChIKey
OTMOUPHCTWPNSL-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
21804
CAS Number
5598-15-2
TTD ID
D0W6PT

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Acetylcholinesterase (AChE) TT1RS9F ACES_HUMAN Inhibitor [2]
Cannabinoid receptor 1 (CB1) TT6OEDT CNR1_HUMAN Inhibitor [1]
Fatty acid amide hydrolase (FAAH) TTDP1UC NOUNIPROTAC Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1-acyl-sn-glycerol-3-phosphate acyltransferase beta (AGPAT2) OT5I4Y9K PLCB_HUMAN Gene/Protein Processing [3]
Acetylcholinesterase (ACHE) OT2H8HG6 ACES_HUMAN Gene/Protein Processing [4]
Acylamino-acid-releasing enzyme (APEH) OTX258QE ACPH_HUMAN Gene/Protein Processing [5]
Albumin (ALB) OTVMM513 ALBU_HUMAN Drug Response [6]
Aromatic-L-amino-acid decarboxylase (DDC) OT0TSW09 DDC_HUMAN Protein Interaction/Cellular Processes [7]
Aryl hydrocarbon receptor (AHR) OTFE4EYE AHR_HUMAN Gene/Protein Processing [8]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [9]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [3]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [10]
Cholinesterase (BCHE) OTOH3WQ9 CHLE_HUMAN Gene/Protein Processing [4]
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 Monoacylglycerol lipase regulates 2-arachidonoylglycerol action and arachidonic acid levels. Bioorg Med Chem Lett. 2008 Nov 15;18(22):5875-8.
2 Activation of the endocannabinoid system by organophosphorus nerve agents. Nat Chem Biol. 2008 Jun;4(6):373-8.
3 Concentration-dependent effects of chlorpyrifos oxon on peroxisome proliferator-activated receptor signaling in MCF-7 cells. Toxicol In Vitro. 2022 Feb;78:105268. doi: 10.1016/j.tiv.2021.105268. Epub 2021 Oct 29.
4 An evaluation of the inhibition of human butyrylcholinesterase and acetylcholinesterase by the organophosphate chlorpyrifos oxon. Toxicol Appl Pharmacol. 2009 Dec 1;241(2):135-42.
5 Blood acylpeptide hydrolase activity is a sensitive marker for exposure to some organophosphate toxicants. Toxicol Sci. 2005 Aug;86(2):291-9. doi: 10.1093/toxsci/kfi195. Epub 2005 May 11.
6 Serum albumins and detoxication of anti-cholinesterase agents. Chem Biol Interact. 2010 Sep 6;187(1-3):325-9. doi: 10.1016/j.cbi.2010.03.001. Epub 2010 Mar 6.
7 Decarboxylases as hypothetical targets for actions of organophosphates: Molecular modeling for prediction of hidden and unexpected health threats. Food Chem Toxicol. 2022 Mar;161:112856. doi: 10.1016/j.fct.2022.112856. Epub 2022 Feb 11.
8 Chlorpyrifos-induced cell proliferation in human breast cancer cell lines differentially mediated by estrogen and aryl hydrocarbon receptors and KIAA1363 enzyme after 24?h and 14 days exposure. Chemosphere. 2020 Jul;251:126426. doi: 10.1016/j.chemosphere.2020.126426. Epub 2020 Mar 6.
9 Effect of chlorpyrifos on efflux transporter gene expression and function in Caco-2 cells. Toxicol In Vitro. 2004 Aug;18(4):403-9. doi: 10.1016/j.tiv.2003.12.006.
10 Identification of environmental chemicals that activate p53 signaling after in vitro metabolic activation. Arch Toxicol. 2022 Jul;96(7):1975-1987. doi: 10.1007/s00204-022-03291-5. Epub 2022 Apr 18.