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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2D Structure
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Physico-chemical Properties
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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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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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
International Nonproprietary Names Click here for help
INN number INN
4362 rolipram
Synonyms Click here for help
(±)-rolipram | (R,S)-rolipram
Database Links Click here for help
CAS Registry No. 61413-54-5
ChEBI CHEBI:104872
ChEMBL Ligand CHEMBL63
DrugBank Ligand DB04149, DB03606
GtoPdb PubChem SID 178101944
PubChem CID 5092
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SynPHARM 13765 (in complex with phosphodiesterase 4B)
13769 (in complex with phosphodiesterase 4D)
Wikipedia Rolipram

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Tocris
Rolipram
Cat. No. 0905