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Compound Detail

CHEMBL132589

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O=C([O-])COc1cccc(C[C@@H]2CCCC=C2c2nc(-c3ccccc3)c(-c3ccccc3)o2)c1.[Na+]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL132589
Phase Preclinical
Structure Type MOL
InChI Key DPECFBBZFTXROT-JIDHJSLPSA-M
Parent Compound CHEMBL1205677
Active Moiety CHEMBL1205677
8
Targets
23
Activities
2
Assay Types
27
PK Parameters
20
Publications
0
Known Names

Molecular Properties

465.6
MW (Da)
6.90
ALogP
4
HBA
1
HBD
72.6
PSA (Ų)
0.31
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C30H26NNaO4
MW 487.53
Aromatic Rings 4
Heavy Atoms 35
NP-Likeness -0.15

Activity Summary

IC50 12 meas. best 8.92
Ki 11 meas. best 7.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Rattus norvegicus
CHEMBL376
 IC50 8.92 6.92 1.2 3
Canis familiaris
CHEMBL373
 IC50 8.89 6.89 1.3 3
Prostacyclin receptor
CHEMBL1995
 Ki 7.27 7.2617 54.0 6
Prostacyclin receptor
CHEMBL1995
 IC50 7.22 7.22 60.0 1
Homo sapiens
CHEMBL372
 IC50 7.22 7.22 60.0 2
Unchecked
CHEMBL612545
 IC50 7.22 6.975 60.0 2
Prostaglandin E2 receptor EP4 subtype
CHEMBL1836
 Ki 5.99 5.99 1020.0 3
Prostacyclin receptor
CHEMBL3322
 IC50 5.92 5.92 1200.0 1
Prostaglandin E2 receptor EP3 subtype
CHEMBL3710
 Ki 5.17 5.17 6800.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 147.0 ng.hr.mL-1 Rattus norvegicus
AUC 391.7 ng.hr.mL-1 Canis lupus familiaris
AUC 147.0 ng.hr.mL-1 Rattus norvegicus
AUC 147.0 ng.hr.mL-1 Rattus norvegicus
CL 17.7 mL.min-1.kg-1 Rattus norvegicus
CL 1.09 mL.min-1.kg-1 Canis lupus familiaris
CL 17.7 mL.min-1.kg-1 Rattus norvegicus
CL 1.77 mL.min-1.kg-1 Rattus norvegicus
CL 1.59 mL.min-1.kg-1 Canis lupus familiaris
Cmax 35.23 nM Rattus norvegicus
Cmax 83.13 nM Canis lupus familiaris
Cmax 35.23 nM Rattus norvegicus
Cmax 35.23 nM Rattus norvegicus
Cmax 1271.61 nM Canis lupus familiaris
Cmax 35.23 nM Rattus norvegicus
F 50.0 % Rattus norvegicus
F 72.0 % Canis lupus familiaris
F 50.0 % Rattus norvegicus
F 72.0 % Canis lupus familiaris
F 50.0 % Rattus norvegicus
T1/2 6.6 hr Rattus norvegicus
T1/2 26.0 hr Canis lupus familiaris
T1/2 6.6 hr Rattus norvegicus
T1/2 3.0 hr Canis lupus familiaris
T1/2 6.6 hr Rattus norvegicus
Tmax 0.3 hr Rattus norvegicus
Tmax 2.3 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Rattus norvegicus IC50 = 1.2 nM 8.92 In vitro inhibition of ADP-induced platelet aggregation using rat platelet rich ... 14643308
Canis familiaris IC50 = 1.3 nM 8.89 In vitro inhibition of ADP-induced platelet aggregation using dog platelet rich ... 14643308
Prostacyclin receptor Ki = 54.0 nM 7.27 Displacement of [3H]iloprost from human Prostanoid IP receptor 15914004
Prostacyclin receptor Ki = 54.0 nM 7.27 Inhibition of [3H]iloprost binding to human prostanoid IP receptor 15857112
Prostacyclin receptor Ki = 54.0 nM 7.27 In vitro Prostacyclin (PGI-2) receptor binding assay was determined based on dis... 14643308
Prostacyclin receptor Ki = 54.0 nM 7.27 Ability to inhibit binding of [3H]iloprost to cloned human prostaglandin I2 rece... 15935660
Prostacyclin receptor Ki = 54.0 nM 7.27 Inhibition of [3H]-Iloprost binding to human Prostanoid IP receptor 15935659
Homo sapiens IC50 = 60.0 nM 7.22 In vitro inhibition of ADP-induced platelet aggregation using human platelet ric... 14643308
Unchecked IC50 = 60.0 nM 7.22 In vitro inhibition of ADP-induced platelet aggregation in human platelet rich p... 15935660
Homo sapiens IC50 = 60.0 nM 7.22 Inhibition of ADP-induced aggregation of human platelets 15935659
Prostacyclin receptor IC50 = 60.0 nM 7.22 Agonist activity at human PGI2 receptor assessed as inhibition of ADP-induced pl... 16837197
Prostacyclin receptor Ki = 60.0 nM 7.22 Displacement of [3H]iloprost from cloned human PGI2 receptor 16837197
Unchecked IC50 = 188.0 nM 6.73 Inhibition of ADP-induced aggregation of monkey platelets 15935659
Prostaglandin E2 receptor EP4 subtype Ki = 1020.0 nM 5.99 Inhibition of [3H]PGE-2 binding to human prostanoid EP4 receptor 15857112
Prostaglandin E2 receptor EP4 subtype Ki = 1020.0 nM 5.99 Inhibition of [3H]PGE-2 binding to Prostanoid EP4 receptor 15935659
Prostaglandin E2 receptor EP4 subtype Ki = 1020.0 nM 5.99 Displacement of [3H]PGE-2 from human Prostanoid EP4 receptor 15914004
Prostacyclin receptor IC50 = 1200.0 nM 5.92 Agonist activity at rat PGI2 receptor assessed as inhibition of ADP-induced plat... 16837197
Rattus norvegicus IC50 = 1200.0 nM 5.92 Inhibition of ADP-induced aggregation of rat platelets 15935659
Rattus norvegicus IC50 = 1200.0 nM 5.92 In vitro inhibition of ADP-induced platelet aggregation in rat platelet rich pla... 15935660
Canis familiaris IC50 = 1300.0 nM 5.89 Inhibition of ADP-induced aggregation of dog platelets 15935659

Literature References

PubMed DOI Target Context # Activities
15857112 10.1021/jm050085k ADMET 8
14643308 10.1016/j.bmcl.2003.09.054 Rattus norvegicus 7
14643308 10.1016/j.bmcl.2003.09.054 Canis familiaris 7
15935659 10.1016/j.bmcl.2005.04.076 ADMET 5
16837197 10.1016/j.bmcl.2006.06.076 Prostacyclin receptor 3
16837197 10.1016/j.bmcl.2006.06.076 Rattus norvegicus 3
15935659 10.1016/j.bmcl.2005.04.076 Rattus norvegicus 2
15935659 10.1016/j.bmcl.2005.04.076 Prostacyclin receptor 1
15935659 10.1016/j.bmcl.2005.04.076 Prostaglandin E2 receptor EP3 subtype 1
15935659 10.1016/j.bmcl.2005.04.076 Prostaglandin E2 receptor EP1 subtype 1
15935659 10.1016/j.bmcl.2005.04.076 Thromboxane A2 receptor 1
15935659 10.1016/j.bmcl.2005.04.076 Prostaglandin F2-alpha receptor 1
15935659 10.1016/j.bmcl.2005.04.076 Prostaglandin D2 receptor 1
14643308 10.1016/j.bmcl.2003.09.054 Homo sapiens 1
15935659 10.1016/j.bmcl.2005.04.076 Unchecked 1
15935659 10.1016/j.bmcl.2005.04.076 Homo sapiens 1
15935660 10.1016/j.bmcl.2005.04.042 Prostacyclin receptor 1
15935660 10.1016/j.bmcl.2005.04.042 Canis familiaris 1
15935660 10.1016/j.bmcl.2005.04.042 Rattus norvegicus 1
15935660 10.1016/j.bmcl.2005.04.042 Unchecked 1

Data from ChEMBL 36 via Core Engine