Compound Detail

CHEMBL26260

BETA-NAPHTHOFLAVONE

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

O=c1cc(-c2ccccc2)oc2ccc3ccccc3c12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL26260
Name	BETA-NAPHTHOFLAVONE
Phase	Preclinical
Structure Type	MOL
InChI Key	OUGIDAPQYNCXRA-UHFFFAOYSA-N

Targets

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	0.44

Activity Summary

IC50 9 meas. best 7.29

EC50 5 meas. best 8.08

Ki 4 meas. best 7.58

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Aryl hydrocarbon receptor CHEMBL3201	EC50	8.08	6.4075	8.4	4
Unchecked CHEMBL612545	Ki	7.58	7.235	26.0	2
Unchecked CHEMBL612545	IC50	7.29	7.29	51.1	1
Cytochrome P450 1A1 CHEMBL2231	IC50	7.27	7.27	54.0	1
Cytochrome P450 1A2 CHEMBL3356	IC50	7.08	6.7667	83.5	3
GABA-A receptor; anion channel CHEMBL1907607	Ki	5.83	5.83	1480.0	1
Tyrosine-protein kinase Fyn CHEMBL1841	IC50	5.6	5.6	2514.9	1
Mitogen-activated protein kinase 3 CHEMBL3385	IC50	5.26	5.26	5466.7	1
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	5.22	5.15	6050.0	2
HepG2 CHEMBL395	EC50	5.1	5.1	8000.0	1
Adenosine receptor A1 CHEMBL318	Ki	5.06	5.06	8800.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Aryl hydrocarbon receptor	EC50	=	8.4	nM	8.08	Agonist activity at AhR (unknown origin)	31727470
Unchecked	Ki	=	26.0	nM	7.58	Compound was evaluated for inhibition constant, in liver microsomes from 3-methy...	7277387
Unchecked	IC50	=	51.06	nM	7.29	Inhibition of porcine CEase using para-nitrophenyl butyrate as substrate preincu...	30108939
Cytochrome P450 1A1	IC50	=	54.0	nM	7.27	Inhibition of CYP1A1 (unknown origin)-mediated deethylation of resorufin ethyl e...	23600958
Cytochrome P450 1A2	IC50	=	83.5	nM	7.08	Inhibition of CYP1A2 in human liver microsomes using Phenacetin as substrate mea...	33515864
Unchecked	Ki	=	130.0	nM	6.89	Compound was evaluated for inhibition constant, in liver microsomes from beta-na...	7277387
Cytochrome P450 1A2	IC50	=	130.0	nM	6.89	Inhibition of CYP1A2 in human liver microsomes incubated for 15 mins by LC-MS/MS...	38294952
Cytochrome P450 1A2	IC50	=	470.0	nM	6.33	Inhibition of CYP1A2 (unknown origin)-mediated demethylation of resorufin methyl...	23600958
Aryl hydrocarbon receptor	EC50	=	1400.0	nM	5.85	Agonist activity at aryl hydrocarbon receptor in human MCF7 cells after 24 hrs C...	20060304
Aryl hydrocarbon receptor	EC50	=	1400.0	nM	5.85	Agonist activity at AhR (unknown origin)	35033884
Aryl hydrocarbon receptor	EC50	=	1400.0	nM	5.85	Agonist activity at AhR in human MCF-7 cells assessed as increase of CYP1A1-depe...	21344906
GABA-A receptor; anion channel	Ki	=	1480.0	nM	5.83	In vitro affinity against Benzodiazepine receptor binding to rat cortical membra...	10543878
Tyrosine-protein kinase Fyn	IC50	=	2514.9	nM	5.6	DRUGMATRIX: Protein Tyrosine Kinase, Fyn enzyme inhibition (substrate: Poly(Glu:...	-
Mitogen-activated protein kinase 3	IC50	=	5466.7	nM	5.26	DRUGMATRIX: Protein Serine/Threonine Kinase, ERK1 enzyme inhibition (substrate: ...	-
Broad substrate specificity ATP-binding cassette transporter ABCG2	IC50	=	6050.0	nM	5.22	Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of ph...	23851114
HepG2	EC50	=	8000.0	nM	5.1	Induction of ARE in human HepG2 cells by luciferase assay	16562850
Broad substrate specificity ATP-binding cassette transporter ABCG2	IC50	=	8320.0	nM	5.08	Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of Ho...	23851114
Adenosine receptor A1	Ki	=	8800.0	nM	5.06	Displacement of specific [3H]PIA binding from adenosine A1 receptor in rat brain...	8576921

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	726
7277387	10.1021/jm00139a011	NON-PROTEIN TARGET	12
7277387	10.1021/jm00139a011	Unchecked	4
31952965	10.1016/j.bmcl.2020.126959	Aryl hydrocarbon receptor	4
8523407	10.1021/jm00025a011	Rattus norvegicus	4
20392544	10.1016/j.ejmech.2010.03.023	NAD(P)H dehydrogenase [quinone] 1	3
22497764	10.1016/j.bmcl.2012.03.070	Rattus norvegicus	3
21344906	10.1021/jm101356p	No relevant target	2
20060304	10.1016/j.bmc.2009.12.036	No relevant target	2
12538803	10.1124/jpet.102.043547	Multidrug resistance associated protein	2
23851114	10.1016/j.ejmech.2013.06.035	Broad substrate specificity ATP-binding cassette transporter ABCG2	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
19200740	10.1016/j.bmc.2008.12.052	NAD(P)H dehydrogenase [quinone] 1	2
17316918	10.1016/j.ejmech.2006.12.012	Unchecked	2
-	10.1007/s00044-011-9575-7	Aryl hydrocarbon receptor	2
30108939	10.1039/C7MD00565B	Unchecked	2
10543878	10.1021/jm991010h	GABA-A receptor; anion channel	2
14684315	10.1016/j.bmcl.2003.10.002	Aryl hydrocarbon receptor	2
38294952	10.1021/acs.jmedchem.3c02040	Cytochrome P450 1A2	1
17291041	10.1021/np060505o	Quinone oxidoreductase	1

Data from ChEMBL 36 via Core Engine