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))
Compound class: Natural product or derivative
Comment: An antibacterial substance derived from Penicillium stoloniferum, and related species. Inhibits inosine-5'-monophosphate dehydrogenase (IMPDH).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

mycophenolic acid is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (2009))
Prodrug mycophenolate mofetil
IUPAC Name Click here for help
(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
International Nonproprietary Names Click here for help
INN number INN
2950 mycophenolic acid
Synonyms Click here for help
ERL-080 | Myfortic® (mycophenolate sodium)
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9678847, R-ALL-9695383
Reactome Reaction Reactome logo R-HSA-9695415, R-HSA-9678749
Other databases
CAS Registry No. 24280-93-1
ChEBI CHEBI:168396
ChEMBL Ligand CHEMBL866
DrugBank Ligand DB01024
DrugCentral Ligand 1860
GtoPdb PubChem SID 178103438
PubChem CID 446541
RCSB PDB Ligand MOA
Search Google for chemical match using the InChIKey HPNSFSBZBAHARI-RUDMXATFSA-N
Search Google for chemicals with the same backbone HPNSFSBZBAHARI
Search PubMed clinical trials mycophenolic acid
Search PubMed titles mycophenolic acid
Search PubMed titles/abstracts mycophenolic acid
UniChem Compound Search for chemical match using the InChIKey HPNSFSBZBAHARI-RUDMXATFSA-N
UniChem Connectivity Search for chemical match using the InChIKey HPNSFSBZBAHARI-RUDMXATFSA-N
Wikipedia Mycophenolic_acid

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Tocris
Mycophenolic acid (links to external site)
Cat. No. 1505