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Compound Detail

CHEMBL222715

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CCCCC[C@H](O)/C=C/[C@H]1CCC(=O)N1CCc1ccc(C(=O)O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL222715
Phase Preclinical
Structure Type MOL
InChI Key JDFLTRXXHVSTHR-OCSRFSMESA-N
8
Targets
15
Activities
2
Assay Types
14
PK Parameters
19
Publications
0
Known Names

Molecular Properties

359.5
MW (Da)
3.42
ALogP
3
HBA
2
HBD
77.8
PSA (Ų)
0.50
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H29NO4
MW 359.47
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness 0.50

Activity Summary

Ki 10 meas. best 8.77
EC50 5 meas. best 10.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin E2 receptor EP4 subtype
CHEMBL1836
 EC50 10.7 9.33 0.0 2
Prostaglandin E2 receptor EP4 subtype
CHEMBL2489
 Ki 8.77 8.77 1.7 2
Prostaglandin E2 receptor EP4 subtype
CHEMBL1836
 Ki 8.7 8.62 2.0 2
Prostaglandin E2 receptor EP4 subtype
CHEMBL4086
 EC50 8.51 8.51 3.1 1
Prostaglandin E2 receptor EP2 subtype
CHEMBL1881
 EC50 7.82 7.82 15.0 1
Prostaglandin E2 receptor EP3 subtype
CHEMBL4336
 Ki 7.07 7.07 86.0 2
Prostaglandin E2 receptor EP2 subtype
CHEMBL1881
 Ki 6.92 6.905 120.0 2
Prostaglandin E2 receptor EP2 subtype
CHEMBL2488
 Ki 6.47 6.47 340.0 1
Prostaglandin E2 receptor EP2 subtype
CHEMBL4909
 EC50 5.75 5.75 1800.0 1
Prostaglandin E2 receptor EP3 subtype
CHEMBL3710
 Ki 4.96 4.96 11000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 35175.6 ng.hr.mL-1 Rattus norvegicus
AUC 14657.8 ng.hr.mL-1 Rattus norvegicus
AUC 18095.3 ng.hr.mL-1 Rattus norvegicus
CL 41.67 mL.min-1.kg-1 Rattus norvegicus
CL 9.167 mL.min-1.kg-1 Rattus norvegicus
F 33.0 % Rattus norvegicus
F 82.0 % Rattus norvegicus
T1/2 0.78 hr Rattus norvegicus
T1/2 14.3 hr Rattus norvegicus
T1/2 31.61 hr Rattus norvegicus
T1/2 20.77 hr Rattus norvegicus
Tmax 0.083 hr Rattus norvegicus
Tmax 0.25 hr Rattus norvegicus
Tmax 4.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin E2 receptor EP4 subtype EC50 = 0.02 nM 10.7 Agonist activity at human EP4 receptor by cAMP assay 18039575
Prostaglandin E2 receptor EP4 subtype Ki = 1.7 nM 8.77 Displacement of [3H]-PGE2 from mouse EP4 receptor expressed in CHO cells after 6... 22119471
Prostaglandin E2 receptor EP4 subtype Ki = 1.7 nM 8.77 Displacement of [3H]-PGE2 from mouse EP4 receptor expressed in CHO cells after 6... 22386979
Prostaglandin E2 receptor EP4 subtype Ki = 2.0 nM 8.7 Displacement of [3H]PGE4 from human EP4 receptor 18039575
Prostaglandin E2 receptor EP4 subtype Ki = 2.9 nM 8.54 Binding affinity to human EP4 receptor 15566283
Prostaglandin E2 receptor EP4 subtype EC50 = 3.1 nM 8.51 Agonist activity at rat EP4 receptor 22386979
Prostaglandin E2 receptor EP4 subtype EC50 = 11.0 nM 7.96 Functional activity at human EP4 receptor 15566283
Prostaglandin E2 receptor EP2 subtype EC50 = 15.0 nM 7.82 Agonist activity at human EP2 receptor by cAMP assay 18039575
Prostaglandin E2 receptor EP3 subtype Ki = 86.0 nM 7.07 Displacement of [3H]-PGE2 from mouse EP3 receptor expressed in CHO cells after 6... 22119471
Prostaglandin E2 receptor EP3 subtype Ki = 86.0 nM 7.07 Displacement of [3H]-PGE2 from mouse EP3 receptor expressed in CHO cells after 6... 22386979
Prostaglandin E2 receptor EP2 subtype Ki = 120.0 nM 6.92 Displacement of [3H]PGE2 from human EP2 receptor 18039575
Prostaglandin E2 receptor EP2 subtype Ki = 130.0 nM 6.89 Binding affinity to human EP2 receptor 15566283
Prostaglandin E2 receptor EP2 subtype Ki = 340.0 nM 6.47 Displacement of [3H]-PGE2 from mouse EP2 receptor expressed in CHO cells after 6... 22119471
Prostaglandin E2 receptor EP2 subtype EC50 = 1800.0 nM 5.75 Agonist activity at rat EP2 receptor 22386979
Prostaglandin E2 receptor EP3 subtype Ki = 11000.0 nM 4.96 Binding affinity to human EP3 receptor 15566283

Literature References

PubMed DOI Target Context # Activities
18039575 10.1016/j.bmcl.2007.11.020 Rattus norvegicus 13
18039575 10.1016/j.bmcl.2007.11.020 Mus musculus 4
15566283 10.1021/jm049290a Prostaglandin E2 receptor EP4 subtype 2
22386979 10.1016/j.bmc.2012.02.018 Prostaglandin E2 receptor EP4 subtype 2
15566283 10.1021/jm049290a Rattus norvegicus 2
18039575 10.1016/j.bmcl.2007.11.020 Prostaglandin E2 receptor EP2 subtype 2
18039575 10.1016/j.bmcl.2007.11.020 Prostaglandin E2 receptor EP4 subtype 2
18039575 10.1016/j.bmcl.2007.11.020 Cavia porcellus 2
22386979 10.1016/j.bmc.2012.02.018 Prostaglandin E2 receptor EP2 subtype 2
- 10.6019/CHEMBL5441142 Schistosoma mansoni 1
15566283 10.1021/jm049290a Prostaglandin E2 receptor EP2 subtype 1
22386979 10.1016/j.bmc.2012.02.018 Prostaglandin E2 receptor EP3 subtype 1
22386979 10.1016/j.bmc.2012.02.018 Prostaglandin E2 receptor EP1 subtype 1
22119471 10.1016/j.bmcl.2011.10.109 Prostaglandin E2 receptor EP4 subtype 1
22119471 10.1016/j.bmcl.2011.10.109 Prostaglandin E2 receptor EP3 subtype 1
22119471 10.1016/j.bmcl.2011.10.109 Prostaglandin E2 receptor EP2 subtype 1
22119471 10.1016/j.bmcl.2011.10.109 Prostaglandin E2 receptor EP1 subtype 1
15566283 10.1021/jm049290a Prostaglandin E2 receptor EP1 subtype 1
15566283 10.1021/jm049290a Prostaglandin E2 receptor EP3 subtype 1

Data from ChEMBL 36 via Core Engine