Details of the Drug

General Information of Drug (ID: DMJ03UM)

Drug Name
ROLIPRAM
Synonyms
61413-54-5; ZK 62711; Rolipramum; Rolipramum [Latin]; 4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone; Adeo; Rolipram [USAN:INN]; 4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one; 4-(3-(cyclopentyloxy)-4-methoxyphenyl)pyrrolidin-2-one; 4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-2-pyrrolidinone; (R,S)-rolipram; ZK-62711; CHEMBL63; EINECS 262-771-1; BRN 1588548; MLS000069691; CHEBI:104872; HJORMJIFDVBMOB-UHFFFAOYSA-N; 4-(3-Cyclopentyloxy-4-methoxyphenyl)-2-pyrrolidone; [3H]rolipram
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 275.34
Logarithm of the Partition Coefficient (xlogp) 2.2
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C16H21NO3
IUPAC Name
4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one
Canonical SMILES
COC1=C(C=C(C=C1)C2CC(=O)NC2)OC3CCCC3
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)
InChIKey
HJORMJIFDVBMOB-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5092
ChEBI ID
CHEMBL63
CAS Number
61413-54-5
UNII
K676NL63N7
DrugBank ID
DB01954
TTD ID
D0T5PO
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Phosphodiesterase 4A (PDE4A) TTZ97H5 PDE4A_HUMAN Inhibitor [2]
Phosphodiesterase 4B (PDE4B) TTVIAT9 PDE4B_HUMAN Inhibitor [3]
Phosphodiesterase 4D (PDE4D) TTSKMI8 PDE4D_HUMAN Inhibitor [4]
Phosphodiesterase 5A (PDE5A) TTJ0IQB PDE5A_HUMAN Inhibitor [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [6]
Metalloproteinase inhibitor 1 (TIMP1) OTOXC51H TIMP1_HUMAN Gene/Protein Processing [6]
Mothers against decapentaplegic homolog 1 (SMAD1) OTQSHR25 SMAD1_HUMAN Gene/Protein Processing [6]
Mothers against decapentaplegic homolog 4 (SMAD4) OTWQWCKG SMAD4_HUMAN Gene/Protein Processing [6]
Transforming growth factor beta-1 proprotein (TGFB1) OTV5XHVH TGFB1_HUMAN Protein Interaction/Cellular Processes [6]
Vimentin OTGZLW4J VIME_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Phosphodiesterase 4A (PDE4A) DTT PDE4A 9.26E-01 -3.01E-03 -0.01
Phosphodiesterase 4B (PDE4B) DTT PDE4B 2.75E-01 -0.13 -0.3
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5313).
2 Discovery of micromolar PDE IV inhibitors that exhibit much reduced affinity for the [3H]rolipram binding site: 3-norbornyloxy-4-methoxyphenylmethylene oxindoles, Bioorg. Med. Chem. Lett. 5(17):1965-1968 (1995).
3 Novel heterocyclic-fused pyridazinones as potent and selective phosphodiesterase IV inhibitors. J Med Chem. 1997 May 9;40(10):1417-21.
4 In silico search for multi-target anti-inflammatories in Chinese herbs and formulas. Bioorg Med Chem. 2010 Mar 15;18(6):2204-2218.
5 Cyclic GMP phosphodiesterase inhibitors. 2. Requirement of 6-substitution of quinazoline derivatives for potent and selective inhibitory activity. J Med Chem. 1994 Jun 24;37(13):2106-11.
6 Rolipram suppresses migration and invasion of human choriocarcinoma cells by inhibiting phosphodiesterase 4-mediated epithelial-mesenchymal transition. J Biochem Mol Toxicol. 2023 Jul;37(7):e23363. doi: 10.1002/jbt.23363. Epub 2023 Apr 5.