Compound Detail

CHEMBL461571

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Cc1c(C(=O)c2ccc(Cl)cc2)c2ccc(OC(F)(F)F)cc2n1Cc1cccc(O[C@H](C)C(=O)O)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL461571
Phase	Preclinical
Structure Type	MOL
InChI Key	DHUATBAZHILHIC-MRXNPFEDSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

531.9

MW (Da)

6.63

ALogP

HBA

HBD

77.8

PSA (Å²)

0.26

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C27H21ClF3NO5
MW	531.91
Aromatic Rings	4
Heavy Atoms	37
NP-Likeness	-1.09

Activity Summary

IC50 29 meas. best 7.96

EC50 6 meas. best 8.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Peroxisome proliferator-activated receptor gamma CHEMBL235	EC50	8.4	8.305	4.0	4
Peroxisome proliferator-activated receptor gamma CHEMBL235	IC50	7.96	7.96	11.0	1
Peroxisome proliferator-activated receptor alpha CHEMBL2128	EC50	7.55	7.55	28.0	1
Peroxisome proliferator-activated receptor alpha CHEMBL239	EC50	6.5	6.5	320.0	1
Substance-K receptor CHEMBL2327	IC50	6.28	6.28	530.0	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	6.11	6.11	770.0	1
D(3) dopamine receptor CHEMBL234	IC50	6.08	6.08	837.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	6.01	6.01	970.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	5.94	5.94	1140.0	1
Prostaglandin E2 receptor EP3 subtype CHEMBL3710	IC50	5.91	5.91	1220.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	5.87	5.87	1340.0	1
D(1A) dopamine receptor CHEMBL2056	IC50	5.82	5.82	1530.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	IC50	5.81	5.81	1560.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	5.79	5.79	1640.0	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	5.78	5.78	1650.0	1
Delta-type opioid receptor CHEMBL236	IC50	5.77	5.77	1690.0	1
Mu-type opioid receptor CHEMBL233	IC50	5.73	5.73	1860.0	1
Thromboxane A2 receptor CHEMBL2069	IC50	5.69	5.69	2030.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	5.67	5.67	2160.0	1
Epidermal growth factor receptor CHEMBL203	IC50	5.65	5.65	2240.0	1
Prostaglandin F2-alpha receptor CHEMBL1987	IC50	5.56	5.56	2730.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.49	5.49	3230.0	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	5.47	5.47	3410.0	1
Kappa-type opioid receptor CHEMBL237	IC50	5.46	5.46	3480.0	1
D(2) dopamine receptor CHEMBL217	IC50	5.45	5.45	3550.0	1
Prostaglandin E2 receptor EP4 subtype CHEMBL1836	IC50	5.43	5.43	3700.0	1
Beta-1 adrenergic receptor CHEMBL213	IC50	5.39	5.39	4070.0	1
Beta-3 adrenergic receptor CHEMBL246	IC50	5.31	5.31	4860.0	1
Prostacyclin receptor CHEMBL1995	IC50	5.2	5.2	6340.0	1
Prostaglandin D2 receptor CHEMBL4427	IC50	5.07	5.07	8450.0	1
Unchecked CHEMBL612545	IC50	4.65	4.595	22500.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	585.1	ng.hr.mL-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Peroxisome proliferator-activated receptor gamma	EC50	=	4.0	nM	8.4	Agonist activity at human PPARgamma receptor expressed in african green monkey C...	19530681
Peroxisome proliferator-activated receptor gamma	EC50	=	5.0	nM	8.3	Partial agonist activity at human PPARgamma LBD assessed as activation of PGC1 b...	22070604
Peroxisome proliferator-activated receptor gamma	EC50	=	5.0	nM	8.3	Partial agonist activity at human PPARgamma LBD assessed as activation of PBP by...	22070604
Peroxisome proliferator-activated receptor gamma	EC50	=	6.0	nM	8.22	Partial agonist activity at human PPARgamma LBD assessed as activation of CBP1-4...	22070604
Peroxisome proliferator-activated receptor gamma	IC50	=	11.0	nM	7.96	Inhibition of human PPARgamma receptor by scintillation proximity assay	19530681
Peroxisome proliferator-activated receptor alpha	EC50	=	28.0	nM	7.55	Agonist activity at mouse PPARalpha receptor expressed in african green monkey C...	19530681
Peroxisome proliferator-activated receptor alpha	EC50	=	320.0	nM	6.5	Agonist activity at human PPARalpha receptor expressed in african green monkey C...	19530681
Substance-K receptor	IC50	=	530.0	nM	6.28	Displacement of radioligand from tachykinin NK2 receptor	18701276
Alpha-2B adrenergic receptor	IC50	=	770.0	nM	6.11	Displacement of radioligand from adrenergic alpha2B receptor	18701276
D(3) dopamine receptor	IC50	=	837.0	nM	6.08	Displacement of radioligand from dopamine D3 receptor	18701276
Sodium-dependent serotonin transporter	IC50	=	970.0	nM	6.01	Displacement of radioligand from SERT	18701276
5-hydroxytryptamine receptor 2B	IC50	=	1140.0	nM	5.94	Displacement of radioligand from 5HT2B receptor	18701276
Prostaglandin E2 receptor EP3 subtype	IC50	=	1220.0	nM	5.91	Inhibition of prostanoid EP3 receptor	18701276
Muscarinic acetylcholine receptor M4	IC50	=	1340.0	nM	5.87	Displacement of radioligand from muscarinic M4 receptor	18701276
D(1A) dopamine receptor	IC50	=	1530.0	nM	5.82	Displacement of radioligand from dopamine D1 receptor	18701276
Muscarinic acetylcholine receptor M3	IC50	=	1560.0	nM	5.81	Displacement of radioligand from muscarinic M3 receptor	18701276
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	1640.0	nM	5.79	Inhibition of 5-Lipoxygenase	18701276
Alpha-2A adrenergic receptor	IC50	=	1650.0	nM	5.78	Displacement of radioligand from adrenergic alpha2A receptor	18701276
Delta-type opioid receptor	IC50	=	1690.0	nM	5.77	Displacement of radioligand from delta opioid receptor	18701276
Mu-type opioid receptor	IC50	=	1860.0	nM	5.73	Displacement of radioligand from mu opioid receptor	18701276

Literature References

PubMed	DOI	Target Context	# Activities
22070604	10.1021/jm201061j	Peroxisome proliferator-activated receptor gamma	8
19530681	10.1021/jm900367w	Peroxisome proliferator-activated receptor gamma	3
19530681	10.1021/jm900367w	Peroxisome proliferator-activated receptor alpha	3
18701276	10.1016/j.bmcl.2008.07.103	Unchecked	2
19530681	10.1021/jm900367w	Mus musculus	2
18701276	10.1016/j.bmcl.2008.07.103	Prostaglandin E2 receptor EP3 subtype	1
18701276	10.1016/j.bmcl.2008.07.103	Prostaglandin E2 receptor EP4 subtype	1
18701276	10.1016/j.bmcl.2008.07.103	Prostaglandin F2-alpha receptor	1
18701276	10.1016/j.bmcl.2008.07.103	Prostacyclin receptor	1
18701276	10.1016/j.bmcl.2008.07.103	Prostaglandin D2 receptor	1
18701276	10.1016/j.bmcl.2008.07.103	Alpha-2B adrenergic receptor	1
18701276	10.1016/j.bmcl.2008.07.103	Beta-1 adrenergic receptor	1
18701276	10.1016/j.bmcl.2008.07.103	Beta-3 adrenergic receptor	1
18701276	10.1016/j.bmcl.2008.07.103	Sodium-dependent noradrenaline transporter	1
18701276	10.1016/j.bmcl.2008.07.103	D(1A) dopamine receptor	1
18701276	10.1016/j.bmcl.2008.07.103	D(2) dopamine receptor	1
18701276	10.1016/j.bmcl.2008.07.103	Voltage-gated inwardly rectifying potassium channel KCNH2	1
18701276	10.1016/j.bmcl.2008.07.103	Sodium-dependent dopamine transporter	1
18701276	10.1016/j.bmcl.2008.07.103	Muscarinic acetylcholine receptor M3	1
18701276	10.1016/j.bmcl.2008.07.103	Epidermal growth factor receptor	1

Data from ChEMBL 36 via Core Engine