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Compound Detail

CHEMBL325795

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

Basic Information

ChEMBL ID CHEMBL325795
Name S-ROLIPRAM
Phase Preclinical
Structure Type MOL
InChI Key HJORMJIFDVBMOB-GFCCVEGCSA-N
6
Targets
9
Activities
3
Assay Types
0
PK Parameters
15
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 7 meas. best 7.59
EC50 1 meas. best 5.47
Kd 1 meas. best 9.18

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vascular endothelial growth factor A, long form
CHEMBL1783
 Kd 9.18 9.18 0.7 1
Zika virus
CHEMBL4296612
 IC50 7.59 7.59 25.8 1
Phosphodiesterase 4
CHEMBL2094267
 IC50 7.35 7.35 45.0 1
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 6.0 5.985 1000.0 2
Phosphodiesterase 4
CHEMBL2093863
 IC50 5.96 5.88 1100.0 2
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 EC50 5.47 5.47 3400.0 1
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 5.37 5.37 4300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vascular endothelial growth factor A, long form Kd = 0.66 nM 9.18 Binding affinity to human VEGF (13 to 107 residues) expressed in Escherichia col... 37409957
Zika virus IC50 = 25.8 nM 7.59 Antiviral activity against Zika virus infected in human A549 cells preincubated ... 29258771
Phosphodiesterase 4 IC50 = 45.0 nM 7.35 Competition of [3H]rolipram binding sites in the central nervous system (HPDE4) ... 9526558
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 1000.0 nM 6.0 Inhibition of PDE4D2 catalytic domain (86 to 413 residues) (unknown origin) 26978121
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 1062.0 nM 5.97 Inhibition of PDE4D2 catalytic domain (86 to 413 residues) (unknown origin) usin... 26978121
Phosphodiesterase 4 IC50 = 1100.0 nM 5.96 Inhibition activity against human monocyte derived PDE4 catalytic activity (LPDE... 9526558
Phosphodiesterase 4 IC50 = 1600.0 nM 5.8 Inhibition of partially-purified PDE 4 from human monocytes 8230117
3',5'-cyclic-AMP phosphodiesterase 4A EC50 = 3400.0 nM 5.47 Induction of SQSTM1-dependent intracellular redistribution of GFP-tagged PDE4A4 ... 21456625
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 4300.0 nM 5.37 Inhibition of full-length PDE4A4 using cAMP as substrate by two-step radiochemic... 21456625

Literature References

PubMed DOI Target Context # Activities
37409957 10.1021/acs.jmedchem.3c00561 Vascular endothelial growth factor A, long form 5
29258771 10.1016/j.bmcl.2017.12.019 A549 4
9526558 10.1021/jm970090r Phosphodiesterase 4 2
9526558 10.1021/jm970090r Cavia porcellus 2
21456625 10.1021/jm200070e 3',5'-cyclic-AMP phosphodiesterase 4A 2
26978121 10.1016/j.ejmech.2015.12.002 3',5'-cyclic-AMP phosphodiesterase 4D 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
8230117 10.1021/jm00074a007 Phosphodiesterase 4 1
9526558 10.1021/jm970090r Mus musculus 1
9526558 10.1021/jm970090r ADMET 1
9526558 10.1021/jm970090r Unchecked 1
29258771 10.1016/j.bmcl.2017.12.019 Zika virus 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1

Data from ChEMBL 36 via Core Engine