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Compound Detail

CHEMBL430893

(-)-ROLIPRAM
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COc1ccc([C@@H]2CNC(=O)C2)cc1OC1CCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL430893
Name (-)-ROLIPRAM
Phase Preclinical
Structure Type MOL
InChI Key HJORMJIFDVBMOB-LBPRGKRZSA-N
9
Targets
23
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

275.4
MW (Da)
2.62
ALogP
3
HBA
1
HBD
47.6
PSA (Ų)
0.92
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C16H21NO3
MW 275.35
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness 0.66

Activity Summary

IC50 20 meas. best 8.3
EC50 2 meas. best 8.4
Kd 1 meas. best 8.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Phosphodiesterase 4
CHEMBL2093863
 Kd 8.8 8.8 1.6 1
Oryctolagus cuniculus
CHEMBL374
 EC50 8.4 8.4 4.0 1
Phosphodiesterase 4
CHEMBL2094267
 IC50 8.3 8.3 5.0 1
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 7.4 6.6029 39.8 7
Phosphodiesterase 4
CHEMBL2093863
 IC50 7.3 6.7425 50.1 4
ADMET
CHEMBL612558
 IC50 7.16 7.16 70.0 1
Zika virus
CHEMBL4296612
 IC50 7.11 7.11 77.6 1
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 6.79 6.15 162.0 3
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 6.64 6.425 231.0 2
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 EC50 6.32 6.32 480.0 1
3',5'-cyclic-AMP phosphodiesterase 4C
CHEMBL291
 IC50 5.43 5.43 3690.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Phosphodiesterase 4 Kd = 1.6 nM 8.8 Binding affinity to human PDE4 assessed as dissociation constant 34042442
Oryctolagus cuniculus EC50 = 4.0 nM 8.4 Stimulation of acid secretion from rabbit parietal glands 9526558
Phosphodiesterase 4 IC50 = 5.0 nM 8.3 Competition of [3H]rolipram binding sites in the central nervous system (HPDE4) ... 9526558
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 39.81 nM 7.4 Inhibition of human recombinant PDE4B by scintillation proximity assay 19656678
Phosphodiesterase 4 IC50 = 50.12 nM 7.3 Inhibition of phosphodiesterase 4 (PDE4) in human neutrophils 11472206
Phosphodiesterase 4 IC50 = 50.12 nM 7.3 Inhibitory concentration against phosphodiesterase 4 (PDE4) in cytosol of human ... 12036360
ADMET IC50 = 70.0 nM 7.16 Inhibition of lipopolysaccharide (LPS)-induced TNF alpha release by human monocy... 9526558
Zika virus IC50 = 77.6 nM 7.11 Antiviral activity against Zika virus infected in human A549 cells preincubated ... 29258771
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 162.0 nM 6.79 Inhibition of human recombinant PDE4A 17228876
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 231.0 nM 6.64 Inhibition of human N-terminal His6-tagged C-terminal FLAG-tagged PDE4B2 express... 26908025
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 231.0 nM 6.64 Inhibition of human His-tagged PDE4B catalytic domain expressed in Escherichia c... 26908025
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 231.0 nM 6.64 Inhibition of human PDE4D2 catalytic domain (79 to 438 residues) Escherichia col... 26908025
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 231.0 nM 6.64 Inhibition of human recombinant PDE4B 17228876
Phosphodiesterase 4 IC50 = 300.0 nM 6.52 Inhibition activity against human monocyte derived PDE4 catalytic activity (LPDE... 9526558
3',5'-cyclic-AMP phosphodiesterase 4A EC50 = 480.0 nM 6.32 Induction of SQSTM1-dependent intracellular redistribution of GFP-tagged PDE4A4 ... 21456625
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 500.0 nM 6.3 Inhibition of human recombinant PDE4B2-mediated cAMP hydrolysis for 30 mins by c... 22297114
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 500.0 nM 6.3 Inhibition of human recombinant PDE4B2 assessed as decrease in cAMP hydrolysis p... 23375225
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 500.0 nM 6.3 Inhibition of human recombinant PDE4B2 assessed as inhibition of cAMP hydrolysis... 24300734
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 550.0 nM 6.26 Inhibition of full-length PDE4A4 using cAMP as substrate by two-step radiochemic... 21456625
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 622.0 nM 6.21 Inhibition of human recombinant PDE4D 17228876

Literature References

PubMed DOI Target Context # Activities
29258771 10.1016/j.bmcl.2017.12.019 A549 4
21456625 10.1021/jm200070e 3',5'-cyclic-AMP phosphodiesterase 4A 2
9526558 10.1021/jm970090r Phosphodiesterase 4 2
9526558 10.1021/jm970090r Cavia porcellus 2
9526558 10.1021/jm970090r Mus musculus 2
9526558 10.1021/jm970090r ADMET 2
26908025 10.1021/acs.jmedchem.5b01813 3',5'-cyclic-AMP phosphodiesterase 4B 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
31013090 10.1021/acs.jmedchem.9b00193 Unchecked 2
12036360 10.1021/jm0110340 Phosphodiesterase 4 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
12036360 10.1021/jm0110340 Unchecked 2
9526558 10.1021/jm970090r Canis familiaris 1
17228876 10.1021/jm060904g 3',5'-cyclic-AMP phosphodiesterase 4A 1
17228876 10.1021/jm060904g 3',5'-cyclic-AMP phosphodiesterase 4B 1
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
9526558 10.1021/jm970090r Unchecked 1
8230117 10.1021/jm00074a007 Phosphodiesterase 4 1
10091677 10.1016/s0960-894x(98)00742-2 Mustela putorius furo 1
10091677 10.1016/s0960-894x(98)00742-2 3',5'-cyclic-AMP phosphodiesterase 4A 1

Data from ChEMBL 36 via Core Engine