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Compound Detail

CHEMBL460026

ICOSAPENT
🧪 Phase III
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🧪 Phase III
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O

Basic Information

ChEMBL ID CHEMBL460026
Name ICOSAPENT
Phase Phase III
Structure Type MOL
InChI Key JAZBEHYOTPTENJ-JLNKQSITSA-N

Known Names

All-cis-fatty acid 20:5 omega-3 C20:5 (n-3) Eicosapentaenoate Eicosapentaenoic acid Eicosapentaenoic acid (c20:5 n3) EPA 45G Icosapent Icosapento Incromega e 7010sr Ropufa 70 Timnodonic acid
11
Targets
13
Activities
4
Assay Types
0
PK Parameters
20
Publications
11
Known Names
20
Indications
1
Mechanisms

Molecular Properties

302.5
MW (Da)
5.99
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.33
QED
1
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C20H30O2
MW 302.46
Aromatic Rings 0
Heavy Atoms 22
NP-Likeness 1.12

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - -

Indications

Adenomatous Polyposis Coli Anorexia Arthritis, Rheumatoid Asthma Bipolar Disorder Cachexia Cardiovascular Diseases Cholestasis Coronary Disease Depressive Disorder Depressive Disorder, Major Glomerulonephritis, IGA Heart Failure Hypertriglyceridemia Intestinal Diseases Obesity Psychotic Disorders Psychotic Disorders Severe Acute Respiratory Syndrome Adenoma

Activity Summary

IC50 10 meas. best 6.52
EC50 1 meas. best 4.44
Kd 1 meas. best 5.7
Ki 1 meas. best 5.12

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 6.52 6.52 300.0 1
Peroxisome proliferator-activated receptor alpha
CHEMBL239
IC50 5.96 5.96 1100.0 2
Peroxisome proliferator-activated receptor gamma
CHEMBL235
IC50 5.8 5.8 1600.0 1
Oxoeicosanoid receptor 1
CHEMBL1628461
IC50 5.7 5.7 2000.0 1
Peroxisome proliferator-activated receptor gamma
CHEMBL235
Kd 5.7 5.7 2000.0 1
Peroxisome proliferator-activated receptor delta
CHEMBL3979
IC50 5.4 5.4 4000.0 1
Prostaglandin G/H synthase 2
CHEMBL4102
IC50 5.15 5.15 7100.0 1
Retinoic acid receptor RXR-alpha
CHEMBL2061
Ki 5.12 5.12 7632.0 1
Prostaglandin G/H synthase 1
CHEMBL2860
IC50 4.89 4.89 13000.0 1
Hepatitis C virus
CHEMBL379
EC50 4.44 4.44 36200.0 1
Aromatase
CHEMBL1978
IC50 4.27 4.27 53200.0 1
Coagulation factor VII/tissue factor
CHEMBL2095194
IC50 4.11 4.11 78000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 300.0 nM 6.52 Inhibition of mPGES1 18459759
Peroxisome proliferator-activated receptor alpha IC50 = 1100.0 nM 5.96 Inhibition of PPAR-alpha (unknown origin) by SPA assay -
Peroxisome proliferator-activated receptor alpha IC50 = 1100.0 nM 5.96 Displacement of [3H]GW2331 from Homo sapiens (human) PPARalpha receptor by scint... -
Peroxisome proliferator-activated receptor gamma IC50 = 1600.0 nM 5.8 Displacement of [3H]BRL49653 from Homo sapiens (human) PPARgamma receptor by sci... -
Oxoeicosanoid receptor 1 IC50 = 2000.0 nM 5.7 Antagonist activity at human OXE receptor fused with G-alphai assessed as inhibi... 24351031
Peroxisome proliferator-activated receptor gamma Kd = 2000.0 nM 5.7 Binding affinity to PPARgamma 22260081
Peroxisome proliferator-activated receptor delta IC50 = 4000.0 nM 5.4 Displacement of [3H]GW2433 from Homo sapiens (human) PPARdelta receptor by scint... -
Prostaglandin G/H synthase 2 IC50 = 7100.0 nM 5.15 Inhibition of sheep COX2-mediated prostaglandin biosynthesis using [1-14C]arachi... 11421736
Retinoic acid receptor RXR-alpha Ki = 7632.0 nM 5.12 Displacement of CU-6PMN from human RXRalpha LBD incubated for 2 hrs by fluoresce... 31483660
Prostaglandin G/H synthase 1 IC50 = 13000.0 nM 4.89 Inhibition of bovine COX1-mediated prostaglandin biosynthesis using [1-14C]arach... 11421736
Hepatitis C virus EC50 = 36200.0 nM 4.44 Antiviral activity against HCV assessed as inhibition of HCV RNA replication in ... 17420205
Aromatase IC50 = 53200.0 nM 4.27 Inhibition of aromatase in human placental microsomes by radiometric method 16643058
Coagulation factor VII/tissue factor IC50 = 78000.0 nM 4.11 Inhibition of amidolytic activity of human tissue factor/human factor 7a 9834151

Literature References

PubMed DOI Target Context # Activities
21903399 10.1016/j.bmc.2011.08.023 Unchecked 4
21903399 10.1016/j.bmc.2011.08.023 RAW264.7 3
16643058 10.1021/np050513p Aromatase 3
20014752 10.1021/tx900326k Hepatotoxicity 3
26784936 10.1021/acs.jmedchem.5b01961 Sterol regulatory element-binding protein 2 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
22822908 10.1021/jm300673z MDA-MB-468 2
21903399 10.1016/j.bmc.2011.08.023 DNA polymerase kappa 2
21903399 10.1016/j.bmc.2011.08.023 DNA polymerase lambda 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
19036594 10.1016/j.bmc.2008.10.083 EA.hy 926 1
21903399 10.1016/j.bmc.2011.08.023 HCT-116 1
21903399 10.1016/j.bmc.2011.08.023 Mus musculus 1
9834151 10.1021/np980117p Trypsin 1
9834151 10.1021/np980117p No relevant target 1
9834151 10.1021/np980117p Coagulation factor VII/tissue factor 1
22260081 10.1021/jm101360s Peroxisome proliferator-activated receptor gamma 1
11421736 10.1021/np000620d Prostaglandin G/H synthase 2 1

Data from ChEMBL 36 via Core Engine