clopidogrel (active metabolite)   Click here for help

GtoPdb Ligand ID: 1772

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: The structure shown here is of the active metabolite of clopidogrel, a pro-drug which is activated via 2-oxo-clopidogrel (PubChem CID 56848893) by cytochrome P450 enzymes in the liver. This compound is an irreversible antagonist of the platelet P2Y12 receptor [3]. The antagonist effect is stereoselective for the S-enantiomer shown here, whereas the R-enantiomer is almost inactive.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 105.64
Molecular weight 355.06
XLogP 1.96
No. Lipinski's rules broken 0
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Canonical SMILES COC(=O)C(c1ccccc1Cl)N1CCC(C(=CC(=O)O)C1)S
Isomeric SMILES COC(=O)[C@H](c1ccccc1Cl)N1CCC(/C(=C\C(=O)O)/C1)S
InChI InChI=1S/C16H18ClNO4S/c1-22-16(21)15(11-4-2-3-5-12(11)17)18-7-6-13(23)10(9-18)8-14(19)20/h2-5,8,13,15,23H,6-7,9H2,1H3,(H,19,20)/b10-8-/t13?,15-/m0/s1
1. Herbert JM, Savi P. (2003)
P2Y12, a new platelet ADP receptor, target of clopidogrel.
Semin Vasc Med, 3 (2): 113-22. [PMID:15199474]
2. Qin C, Zhou J, Gao Y, Lai W, Yang C, Cai Y, Chen S, Du C. (2017)
Critical Role of P2Y12 Receptor in Regulation of Th17 Differentiation and Experimental Autoimmune Encephalomyelitis Pathogenesis.
J Immunol, 199 (1): 72-81. [PMID:28515278]
3. Savi P, Labouret C, Delesque N, Guette F, Lupker J, Herbert JM. (2001)
P2y(12), a new platelet ADP receptor, target of clopidogrel.
Biochem Biophys Res Commun, 283 (2): 379-83. [PMID:11327712]