Compound Detail

CHEMBL364841

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Cc1cc2c(CC(=O)O)cccc2n1C(=O)c1ccc(OC[C@@H]2CN(C)c3ccccc3O2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL364841
Phase	Preclinical
Structure Type	MOL
InChI Key	XECAIYOLUPUKEJ-QFIPXVFZSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

470.5

MW (Da)

4.54

ALogP

HBA

HBD

81.0

PSA (Å²)

0.45

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C28H26N2O5
MW	470.53
Aromatic Rings	4
Heavy Atoms	35
NP-Likeness	-0.57

Activity Summary

Ki 21 meas. best 8.46

IC50 5 meas. best 8.92

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Prostaglandin D2 receptor CHEMBL4427	IC50	8.92	8.08	1.2	2
Prostaglandin D2 receptor CHEMBL3933	IC50	8.62	8.62	2.4	3
Prostaglandin D2 receptor CHEMBL4427	Ki	8.46	8.46	3.5	1
Prostaglandin D2 receptor CHEMBL3933	Ki	8.0	7.85	10.0	4
Prostacyclin receptor CHEMBL1995	Ki	7.43	7.43	37.0	3
Prostaglandin E2 receptor EP2 subtype CHEMBL2488	Ki	7.0	7.0	99.0	3
Thromboxane A2 receptor CHEMBL2069	Ki	6.58	6.58	260.0	2
Prostaglandin E2 receptor EP3 subtype CHEMBL4336	Ki	5.77	5.77	1700.0	3
Prostaglandin F2-alpha receptor CHEMBL5000	Ki	5.51	5.51	3100.0	2
Prostaglandin E2 receptor EP1 subtype CHEMBL2181	Ki	5.21	5.21	6200.0	3

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	7200.0	ng.hr.mL-1	Rattus norvegicus
AUC	24300.0	ng.hr.mL-1	Rattus norvegicus
CL	2.4	mL.min-1.kg-1	Rattus norvegicus
Cmax	7438.42	nM	Rattus norvegicus
F	34.0	%	Rattus norvegicus
T1/2	9.8	hr	Rattus norvegicus
T1/2	5.4	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Prostaglandin D2 receptor	IC50	=	1.2	nM	8.92	Effect on the increase in cAMP formation induced by PGD-2 in the presence of bov...	15341946
Prostaglandin D2 receptor	IC50	=	2.4	nM	8.62	Antagonist activity at mouse DP receptor expressed in CHO cells assessed as inhi...	21737285
Prostaglandin D2 receptor	IC50	=	2.4	nM	8.62	Antagonist activity at mouse prostanoid DP receptor expressed in CHO cells asses...	21885288
Prostaglandin D2 receptor	IC50	=	2.4	nM	8.62	Antagonist activity at mouse prostanoid DP receptor expressed in CHO cells asses...	21982795
Prostaglandin D2 receptor	Ki	=	3.5	nM	8.46	Ability to inhibit the binding of [3H]PGD-2 radioligand to membranes of CHO cell...	15341946
Prostaglandin D2 receptor	Ki	=	10.0	nM	8.0	Ability to inhibit the binding of [3H]PGD-2 radioligand to membranes of CHO cell...	15341946
Prostaglandin D2 receptor	Ki	=	16.0	nM	7.8	Displacement of [3H]-PGD2 from mouse DP receptor expressed in CHO cells after 20...	21737285
Prostaglandin D2 receptor	Ki	=	16.0	nM	7.8	Displacement of [3H]PGD2 from mouse prostanoid DP receptor expressed in CHO cell...	21885288
Prostaglandin D2 receptor	Ki	=	16.0	nM	7.8	Displacement of [3H]-PGD2 from mouse DP receptor expressed in CHO cells after 20...	21982795
Prostacyclin receptor	Ki	=	37.0	nM	7.43	Displacement of [3H]-Iloprost from human IP receptor expressed in CHO cells afte...	21737285
Prostacyclin receptor	Ki	=	37.0	nM	7.43	Displacement of [3H]Iloprost from human prostanoid IP receptor expressed in CHO ...	21885288
Prostacyclin receptor	Ki	=	37.0	nM	7.43	Displacement of [3H]Iloprost from human prostanoid IP receptor expressed in CHO ...	21982795
Prostaglandin D2 receptor	IC50	=	57.0	nM	7.24	Antagonist activity at prostanoid DP receptor in human platelet rich plasma asse...	21982795
Prostaglandin E2 receptor EP2 subtype	Ki	=	100.0	nM	7.0	Ability to inhibit the binding of [3H]-PGD-2 radioligand to membranes of CHO cel...	15341946
Prostaglandin E2 receptor EP2 subtype	Ki	=	99.0	nM	7.0	Displacement of [3H]PGE2 from mouse prostaglandin EP2 receptor expressed in CHO ...	21885288
Prostaglandin E2 receptor EP2 subtype	Ki	=	99.0	nM	7.0	Displacement of [3H]-PGE2 from mouse EP2 receptor expressed in CHO cells after 6...	21737285
Thromboxane A2 receptor	Ki	=	260.0	nM	6.58	Displacement of [3H]-SQ29548 from human TP receptor expressed in CHO cells after...	21737285
Thromboxane A2 receptor	Ki	=	260.0	nM	6.58	Displacement of [3H]-SQ29548 from human prostanoid TP receptor expressed in CHO ...	21885288
Prostaglandin E2 receptor EP3 subtype	Ki	=	1700.0	nM	5.77	Ability to inhibit the binding of [3H]PGD-2 radioligand to membranes of CHO cell...	15341946
Prostaglandin E2 receptor EP3 subtype	Ki	=	1700.0	nM	5.77	Displacement of [3H]-PGE2 from mouse EP3 receptor expressed in CHO cells after 6...	21737285

Literature References

PubMed	DOI	Target Context	# Activities
21885288	10.1016/j.bmc.2011.08.007	Rattus norvegicus	8
21982795	10.1016/j.bmc.2011.08.065	Prostaglandin D2 receptor	3
15341946	10.1016/j.bmcl.2004.07.039	Prostaglandin D2 receptor	3
21982795	10.1016/j.bmc.2011.08.065	Cavia porcellus	3
21885288	10.1016/j.bmc.2011.08.007	Prostaglandin D2 receptor	2
21737285	10.1016/j.bmc.2011.06.014	Cavia porcellus	2
21737285	10.1016/j.bmc.2011.06.014	Prostaglandin D2 receptor	2
21737285	10.1016/j.bmc.2011.06.014	Thromboxane A2 receptor	1
21885288	10.1016/j.bmc.2011.08.007	Prostaglandin E2 receptor EP3 subtype	1
21885288	10.1016/j.bmc.2011.08.007	Prostaglandin E2 receptor EP1 subtype	1
21737285	10.1016/j.bmc.2011.06.014	Unchecked	1
21737285	10.1016/j.bmc.2011.06.014	Prostacyclin receptor	1
15341946	10.1016/j.bmcl.2004.07.039	Prostaglandin E2 receptor EP1 subtype	1
21737285	10.1016/j.bmc.2011.06.014	Prostaglandin F2-alpha receptor	1
21737285	10.1016/j.bmc.2011.06.014	Prostaglandin E2 receptor EP4 subtype	1
21737285	10.1016/j.bmc.2011.06.014	Prostaglandin E2 receptor EP3 subtype	1
21737285	10.1016/j.bmc.2011.06.014	Prostaglandin E2 receptor EP2 subtype	1
21737285	10.1016/j.bmc.2011.06.014	Prostaglandin E2 receptor EP1 subtype	1
15341946	10.1016/j.bmcl.2004.07.039	Prostaglandin E2 receptor EP4 subtype	1
15341946	10.1016/j.bmcl.2004.07.039	Prostaglandin E2 receptor EP3 subtype	1

Data from ChEMBL 36 via Core Engine