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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Immunopharmacology Comments
Experimental evidence indicates that P2Y12 receptors play a critical role in Th17 differentiation (in mouse models of autoimmune inflammatory diseases), and that P2Y12-selective antagonists reverse Th17 differentiation and ameliorate inflammatory sequelae [2]. These findings suggest potential for P2Y12 antagonists as therapeutics for autoimmune diseases.