rolipram   Click here for help

GtoPdb Ligand ID: 5260

Synonyms: (±)-rolipram | (R,S)-rolipram
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Rolipram is a a well-characterized PDE4 inhibitor that has been widely used in research to examine the role(s) played by PDE4 in autoimmune and inflammatory diseases [2-3], Alzheimer's disease [1] and cognition [4]. The INN-assigned preparation of rolipram is a racemic mixture of R-rolipram and S-rolipram. The structure shown here does not specify stereochemistry to represent the mixture. The two stereoisomers are represented on PubChem by CID 448055 and CID 158758, and by the entries on DrugBank linked to in the table above.
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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

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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 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 47.56
Molecular weight 275.15
XLogP 1.89
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 COc1ccc(cc1OC1CCCC1)C1CNC(=O)C1
Isomeric SMILES COc1ccc(cc1OC1CCCC1)C1CNC(=O)C1
InChI InChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)
InChI Key HJORMJIFDVBMOB-UHFFFAOYSA-N
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
phosphodiesterase 4A Hs Inhibitor Inhibition 9.0 pIC50 - 5
⤷ pIC50 9.0 (IC50 1x10-9 M) [5]
phosphodiesterase 4B Hs Inhibitor Inhibition 9.0 pIC50 - 5
⤷ pIC50 9.0 (IC50 1x10-9 M) [5]
phosphodiesterase 4D Hs Inhibitor Inhibition 7.2 pIC50 - 5
⤷ pIC50 7.2 (IC50 6.31x10-8 M) [5]
phosphodiesterase 4C Hs Inhibitor Inhibition 6.5 pIC50 - 5
⤷ pIC50 6.5 (IC50 3.16x10-7 M) [5]