mycophenolic acid   Click here for help

GtoPdb Ligand ID: 6832

Synonyms: ERL-080 | Myfortic® (mycophenolate sodium)
Approved drug PDB Ligand
mycophenolic acid is an approved drug (FDA (2009))
Comment: An antibiotic substance derived from Penicillium stoloniferum, and related species. Inhibits inosine-5'-monophosphate dehydrogenase (IMPDH).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 93.06
Molecular weight 320.13
XLogP 2.21
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1c(CC=C(CCC(=O)O)C)c(O)c2c(c1C)COC2=O
Isomeric SMILES COc1c(C/C=C(/CCC(=O)O)\C)c(O)c2c(c1C)COC2=O
InChI InChI=1S/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/b9-4+
InChI Key HPNSFSBZBAHARI-RUDMXATFSA-N
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Summary of Clinical Use Click here for help
An immunosuppresant and potent anti-proliferative drug. Used clinically (in triple therapy with calcineurin inhibitors and prednisolone) and in research (to detect cellular xanthine guanine phosphoribosyltransferase expression).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Anti-proliferative in T- and B-lymphocytes via inhibition of inosine monophosphate dehydrogenase (IMPDH). Also suppresses antibody formation by B-lymphocytes and may inhibit recruitment of leukocytes into sites of inflammation and graft rejection.