Compound Detail

CHEMBL283196

ALPHA-NAPHTHOFLAVONE

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O=c1cc(-c2ccccc2)oc2c1ccc1ccccc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL283196
Name	ALPHA-NAPHTHOFLAVONE
Phase	Preclinical
Structure Type	MOL
InChI Key	VFMMPHCGEFXGIP-UHFFFAOYSA-N

Targets

161

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

272.3

MW (Da)

4.61

ALogP

HBA

HBD

30.2

PSA (Å²)

0.47

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C19H12O2
MW	272.30
Aromatic Rings	4
Heavy Atoms	21
NP-Likeness	0.37

Activity Summary

IC50 144 meas. best 9.24

Ki 12 meas. best 7.8

EC50 5 meas. best 5.75

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cytochrome P450 1B1 CHEMBL4878	IC50	9.24	7.6123	0.6	35
Cytochrome P450 1A2 CHEMBL3356	IC50	8.7	7.2109	2.0	56
Unchecked CHEMBL612545	IC50	8.46	5.882	3.5	5
Cytochrome P450 1A1 CHEMBL2231	IC50	8.13	7.3115	7.4	26
Cytochrome P450 1B1 CHEMBL4878	Ki	7.8	7.8	16.0	1
Unchecked CHEMBL612545	Ki	7.77	7.695	17.0	2
Aromatase CHEMBL1978	Ki	7.7	7.7	20.0	1
Cytochrome P450 1A2 CHEMBL3356	Ki	7.7	7.7	20.0	1
Aryl hydrocarbon receptor CHEMBL6099	IC50	7.6	7.6	25.0	1
A549 CHEMBL392	IC50	7.48	7.48	32.8	1
Cytochrome P450 1A1 CHEMBL2231	Ki	7.35	7.325	45.0	2
Carboxylic ester hydrolase CHEMBL4105977	IC50	7.32	7.32	47.8	1
Aromatase CHEMBL1978	IC50	7.16	6.43	70.0	2
NCI-H460 CHEMBL396	IC50	6.32	6.32	481.4	1
Adenosine receptor A1 CHEMBL226	Ki	6.18	6.18	660.6	1
Adenosine receptor A1 CHEMBL318	Ki	6.11	6.11	786.0	1
Adenosine receptor A1 CHEMBL226	IC50	5.95	5.95	1132.5	1
Adenosine receptor A2a CHEMBL302	Ki	5.88	5.88	1320.0	1
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	5.88	5.865	1310.0	2
Cytochrome P450 1A1 CHEMBL2231	EC50	5.75	5.625	1800.0	2
Substance-K receptor CHEMBL2327	Ki	5.71	5.71	1949.0	1
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL1827	IC50	5.64	5.64	2303.4	1
DNA-dependent protein kinase catalytic subunit CHEMBL3142	IC50	5.3	5.3	4980.0	1
Cytochrome P450 1B1 CHEMBL4878	EC50	5.29	4.7167	5100.0	3
Substance-K receptor CHEMBL2327	IC50	5.23	5.23	5847.1	1
Thromboxane-A synthase CHEMBL1835	IC50	5.17	5.17	6760.8	1
ADMET CHEMBL612558	IC50	5.0	5.0	10000.0	1
Multidrug resistance-associated protein 1 CHEMBL3004	IC50	4.95	4.95	11300.0	1
Cytochrome P450 2B6 CHEMBL4729	IC50	4.89	4.89	13000.0	1
No relevant target CHEMBL2362975	IC50	4.81	4.81	15550.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	4.61	4.61	24600.0	1
Cytochrome P450 3A6 CHEMBL1743541	Ki	4.1	4.1	80100.0	1
MCF7 CHEMBL387	IC50	4.09	4.09	80700.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Inhibition	98.0	%	Homo sapiens
Inhibition	90.0	%	Homo sapiens
Inhibition	87.0	%	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cytochrome P450 1B1	IC50	=	0.57	nM	9.24	Inhibition of recombinant human CYP1B1 using 7-ER as substrate in presence of NA...	38692523
Cytochrome P450 1B1	IC50	=	1.3	nM	8.89	Inhibition of human CYP1B1 assessed as reduction in 7-ethoxyresorufin O-deethyla...	25799264
Cytochrome P450 1B1	IC50	=	1.88	nM	8.73	Inhibition of human recombinant CYP1B1 assessed as fluorescence of resorufin	37315474
Cytochrome P450 1A2	IC50	=	2.0	nM	8.7	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate inc...	34672559
Unchecked	IC50	=	3.5	nM	8.46	Inhibition of beta-naphthoflavone-induced Cyp1A in rat H4II7 cell	17291041
Cytochrome P450 1A2	IC50	=	3.8	nM	8.42	Inhibition of human CYP1A2 assessed as reduction in 7-ethoxyresorufin O-deethyla...	25799264
Cytochrome P450 1B1	IC50	=	4.0	nM	8.4	Inhibition of recombinant human CYP1B1 expressed in Escherichia coli DH5[alpha] ...	28259840
Cytochrome P450 1B1	IC50	=	4.1	nM	8.39	Inhibition of recombinant human CYP1B1 expressed in baculovirus infected insect ...	31945665
Cytochrome P450 1B1	IC50	=	5.0	nM	8.3	Inhibition of human CYP1B1 assessed as inhibition of 7-ethoxyresorufin O-deethyl...	38509663
Cytochrome P450 1B1	IC50	=	4.97	nM	8.3	Inhibition of recombinant CYP1B1 (unknown origin) using 7-ethoxyresorufin as sub...	38031326
Cytochrome P450 1B1	IC50	=	5.0	nM	8.3	Inhibition of CYP1B1 (unknown origin)	36512763
Cytochrome P450 1B1	IC50	=	5.0	nM	8.3	Inhibition of CYP1B1	17544277
Cytochrome P450 1B1	IC50	=	5.0	nM	8.3	Inhibition of human recombinant CYP1B1 expressed in Escherichia coli membranes a...	25799264
Cytochrome P450 1B1	IC50	=	5.0	nM	8.3	Inhibition of human CYP1B1 expressed in human AHH1 cells	28222316
Cytochrome P450 1B1	IC50	=	5.0	nM	8.3	Inhibition of human CYP1B1 expressed in Escherichia coli DH5alpha coexpressing h...	28458135
Cytochrome P450 1B1	IC50	=	5.2	nM	8.28	Inhibition of human CYP1B1 expressed in Escherichia coli DH5alpha coexpressing h...	28458135
Cytochrome P450 1A2	IC50	=	5.57	nM	8.25	Inhibition of human recombinant CYP1A2 assessed as fluorescence of resorufin	37315474
Cytochrome P450 1B1	IC50	=	5.9	nM	8.23	Inhibition of human recombinant CYP1B1 using 7-ethoxyresorufin as substrate in p...	31830634
Cytochrome P450 1B1	IC50	=	5.9	nM	8.23	Inhibition of recombinant human CYP1B1 using 7-ethoxyresorufin as substrate afte...	33069055
Cytochrome P450 1B1	IC50	=	5.9	nM	8.23	Inhibition of recombinant human CYP1B1 expressed in supersomes using 7-ethoxyres...	31803401

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	558
7277387	10.1021/jm00139a011	NON-PROTEIN TARGET	11
36520541	10.1021/acs.jmedchem.2c01368	Cytochrome P450 1B1	9
28222316	10.1016/j.ejmech.2017.02.016	Cytochrome P450 1B1	9
-	10.6019/CHEMBL5303304	U2OS	7
28117203	10.1016/j.bmcl.2017.01.020	Carboxylic ester hydrolase	6
-	10.6019/CHEMBL5303304	HEK-293T	6
30448188	10.1016/j.bmc.2018.11.013	MCF7	5
38509663	10.1021/acs.jmedchem.4c00164	A549	5
29150398	10.1016/j.bmcl.2017.11.013	Cytochrome P450 1B1	5
29150398	10.1016/j.bmcl.2017.11.013	Cytochrome P450 1A1	5
7277387	10.1021/jm00139a011	Unchecked	5
28259840	10.1016/j.ejmech.2017.02.032	Cytochrome P450 1A1	4
36520541	10.1021/acs.jmedchem.2c01368	Unchecked	4
25799264	10.1021/acs.jmedchem.5b00265	Cytochrome P450 1B1	4
28259840	10.1016/j.ejmech.2017.02.032	Cytochrome P450 1B1	4
38509663	10.1021/acs.jmedchem.4c00164	Cytochrome P450 1B1	4
30613334	10.1021/acsmedchemlett.8b00409	Unchecked	3
30553624	10.1016/j.bmc.2018.11.045	Cytochrome P450 1B1	3
30216063	10.1021/acs.jmedchem.8b00907	Cytochrome P450 1A1	3

Data from ChEMBL 36 via Core Engine