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
References
1. Nelson PH, Eugui E, Wang CC, Allison AC. (1990)
Synthesis and immunosuppressive activity of some side-chain variants of mycophenolic acid.
J Med Chem, 33 (2): 833-8. [PMID:1967654]