Compound Detail

CHEMBL204232

NAPHTHYRIDINONE

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CC(=O)Nc1c(C(C)=O)c(=O)n(C)c2nc(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)cc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL204232
Name	NAPHTHYRIDINONE
Phase	Preclinical
Structure Type	MOL
InChI Key	VHSIAYLBCLUAFT-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

514.8

MW (Da)

6.39

ALogP

HBA

HBD

81.1

PSA (Å²)

0.32

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula	C25H18Cl3N3O3
MW	514.80
Aromatic Rings	4
Heavy Atoms	34
NP-Likeness	-0.96

Activity Summary

Ki 15 meas. best 7.09

IC50 14 meas. best 8.12

EC50 2 meas. best 8.31

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cannabinoid receptor 1 CHEMBL218	EC50	8.31	8.31	4.9	2
Cannabinoid receptor 1 CHEMBL218	IC50	8.12	8.12	7.5	6
Gamma-aminobutyric acid receptor subunit alpha-1 CHEMBL1962	Ki	7.09	7.09	82.0	1
Unchecked CHEMBL612545	Ki	7.09	7.09	81.3	2
Sigma intracellular receptor 2 CHEMBL4105907	Ki	6.22	6.22	602.6	3
Synaptic vesicular amine transporter CHEMBL1893	Ki	6.19	6.19	648.0	1
Adenosine receptor A3 CHEMBL256	Ki	6.11	6.11	773.0	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	6.1	6.1	799.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	5.95	5.95	1130.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	5.94	5.9267	1158.0	3
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	5.87	5.87	1340.0	1
Epidermal growth factor receptor CHEMBL203	IC50	5.49	5.49	3260.0	1
Mitogen-activated protein kinase 14 CHEMBL260	IC50	5.43	5.43	3680.0	1
Cannabinoid receptor 2 CHEMBL253	IC50	5.39	5.36	4100.0	4
Mitogen-activated protein kinase 3 CHEMBL3385	IC50	5.07	5.07	8610.0	1
Nociceptin receptor CHEMBL2014	Ki	5.0	5.0	10000.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	12.0	mL.min-1.kg-1	Rattus norvegicus
CL	13.9	mL.min-1.kg-1	Mus musculus
CL	4.4	mL.min-1.kg-1	Canis lupus familiaris
CL	1.4	mL.min-1.kg-1	Macaca mulatta
CL	12.0	mL.min-1.kg-1	Rattus norvegicus
F	93.0	%	Rattus norvegicus
F	70.0	%	Mus musculus
F	100.0	%	Canis lupus familiaris
F	96.0	%	Macaca mulatta
F	93.0	%	Rattus norvegicus
T1/2	8.0	hr	Rattus norvegicus
T1/2	8.0	hr	Mus musculus
T1/2	24.0	hr	Canis lupus familiaris
T1/2	22.0	hr	Macaca mulatta
T1/2	8.0	hr	Rattus norvegicus
T1/2	8.0	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cannabinoid receptor 1	EC50	=	4.9	nM	8.31	Affinity On-target Cellular interaction (Radioimmunoassay (hCB1r functional acti...	-
Cannabinoid receptor 1	EC50	=	4.9	nM	8.31	Functional activation assay	-
Cannabinoid receptor 1	IC50	=	7.5	nM	8.12	Binding affinity at the CB1 receptor	16263284
Cannabinoid receptor 1	IC50	=	7.5	nM	8.12	Inverse agonist activity at cannabinoid CB1 receptor	19328684
Cannabinoid receptor 1	IC50	=	7.5	nM	8.12	Inhibition of human CB1 receptor	20096577
Cannabinoid receptor 1	IC50	=	7.5	nM	8.12	Binding affinity to human CB1 receptor	20483606
Cannabinoid receptor 1	IC50	=	7.5	nM	8.12	Radioligand Binding Assay (CNR1)	-
Cannabinoid receptor 1	IC50	=	7.5	nM	8.12	Affinity Biochemical interaction (Radioligand binding assay (CNR1)) EUB0000296b...	-
Gamma-aminobutyric acid receptor subunit alpha-1	Ki	=	82.0	nM	7.09	Selectivity interaction (GPCR panel (PDSP screen)) EUB0000296b GABRA1	-
Unchecked	Ki	=	81.28	nM	7.09	GPCRScan assay: inhibition of GABA/PBR	-
Unchecked	Ki	=	82.0	nM	7.09	GPCRScan assay: inhibition of GABA/PBR	-
Sigma intracellular receptor 2	Ki	=	602.56	nM	6.22	GPCRScan assay: inhibition of Sigma 2	-
Sigma intracellular receptor 2	Ki	=	605.0	nM	6.22	GPCRScan assay: inhibition of Sigma 2	-
Sigma intracellular receptor 2	Ki	=	605.0	nM	6.22	Selectivity interaction (GPCR panel (PDSP screen)) EUB0000296b TMEM97	-
Synaptic vesicular amine transporter	Ki	=	648.0	nM	6.19	Selectivity interaction (Radioligand binding assay (MDS Pharma Service)) EUB0000...	-
Adenosine receptor A3	Ki	=	773.0	nM	6.11	Selectivity interaction (Radioligand binding assay (MDS Pharma Service)) EUB0000...	-
Sodium-dependent dopamine transporter	Ki	=	799.0	nM	6.1	Selectivity interaction (Radioligand binding assay (MDS Pharma Service)) EUB0000...	-
Alpha-2C adrenergic receptor	Ki	=	1130.0	nM	5.95	Selectivity interaction (Radioligand binding assay (MDS Pharma Service)) EUB0000...	-
Sigma non-opioid intracellular receptor 1	Ki	=	1158.0	nM	5.94	GPCRScan assay: inhibition of Sigma 1	-
Sigma non-opioid intracellular receptor 1	Ki	=	1158.0	nM	5.94	Selectivity interaction (GPCR panel (PDSP screen)) EUB0000296b SIGMAR1	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL4507287	Tyrosine-protein kinase ABL1	15
-	10.6019/CHEMBL5724558	Colon cancer organoid	12
-	10.6019/CHEMBL5674860	Colon cancer organoid	12
-	10.6019/CHEMBL4507287	Epidermal growth factor receptor	12
-	10.6019/CHEMBL4507287	Receptor-type tyrosine-protein kinase FLT3	11
-	10.6019/CHEMBL4507287	Unchecked	10
-	10.6019/CHEMBL4507287	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	10
-	10.6019/CHEMBL4689842	HEK-293T	10
-	10.6019/CHEMBL4507287	Mast/stem cell growth factor receptor Kit	9
-	10.6019/CHEMBL4689842	Fibroblast	9
-	10.6019/CHEMBL4689842	U2OS	8
16263284	10.1016/j.bmcl.2005.10.028	Rattus norvegicus	8
-	10.6019/CHEMBL5608141	Colon cancer organoid	6
19328684	10.1016/j.bmcl.2009.03.005	Rattus norvegicus	5
-	10.1158/2159-8290.CD-23-0050	Colon cancer organoid	5
16263284	10.1016/j.bmcl.2005.10.028	Mus musculus	5
-	10.6019/CHEMBL4507287	Proto-oncogene tyrosine-protein kinase receptor Ret	4
-	10.6019/CHEMBL4507287	Sigma intracellular receptor 2	3
16263284	10.1016/j.bmcl.2005.10.028	Rhesus monkey	3
-	10.6019/CHEMBL4507287	Sigma non-opioid intracellular receptor 1	3

Data from ChEMBL 36 via Core Engine