Compound Detail

CHEMBL274056

NAPHTHAZALIN

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O=C1C=CC(=O)c2c(O)ccc(O)c21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL274056
Name	NAPHTHAZALIN
Phase	Preclinical
Structure Type	MOL
InChI Key	RQNVIKXOOKXAJQ-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

190.2

MW (Da)

1.03

ALogP

HBA

HBD

74.6

PSA (Å²)

0.60

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	C10H6O4
MW	190.15
Aromatic Rings	1
Heavy Atoms	14
NP-Likeness	1.17

Activity Summary

IC50 19 meas. best 7.1

Ki 2 meas. best 5.65

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
A2780 CHEMBL614004	IC50	7.1	7.1	80.0	1
Aurora kinase A CHEMBL4722	IC50	7.05	7.05	90.0	1
COP9 signalosome complex subunit 5 CHEMBL4105809	IC50	6.77	6.405	170.0	2
Aurora kinase B CHEMBL2185	IC50	6.46	6.46	350.0	1
Replicase polyprotein 1ab CHEMBL4523582	IC50	6.31	6.31	490.0	1
HaCaT CHEMBL614392	IC50	6.16	6.16	700.0	1
HL-60 CHEMBL383	IC50	6.1	6.065	800.0	2
M-phase inducer phosphatase 2 CHEMBL4804	IC50	6.0	6.0	1000.0	1
HCT-116 CHEMBL394	IC50	5.98	5.98	1040.0	1
Cytochrome P450 1A2 CHEMBL3356	IC50	5.67	5.67	2160.0	1
Cytochrome P450 1A2 CHEMBL3356	Ki	5.65	5.65	2220.0	1
Arachidonate 5-lipoxygenase CHEMBL2980	IC50	5.52	5.52	3000.0	1
Cytochrome P450 1A1 CHEMBL2231	Ki	5.44	5.44	3660.0	1
Cytochrome P450 1A1 CHEMBL2231	IC50	5.42	5.42	3820.0	1
HepG2 CHEMBL395	IC50	5.3	5.3	4970.0	1
Dual specificity protein phosphatase 6 CHEMBL5511	IC50	5.16	5.16	6900.0	1
A-375 CHEMBL613859	IC50	5.05	5.05	8850.0	1
Dual specificity protein phosphatase 1 CHEMBL5623	IC50	5.03	5.03	9370.0	1
Thioredoxin reductase CHEMBL2096978	IC50	4.7	4.7	20000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
A2780	IC50	=	80.0	nM	7.1	Antiproliferative activity against human A2780 cells after 2 days by alamar-blue...	19028102
Aurora kinase A	IC50	=	90.0	nM	7.05	Inhibition of Aurora A (122 to 403 residues) (unknown origin) expressed in Esche...	35687347
COP9 signalosome complex subunit 5	IC50	=	170.0	nM	6.77	Inhibition of N-terminal His6-tagged CSN5 (2 to 257 residues) (unknown origin) t...	39129245
Aurora kinase B	IC50	=	350.0	nM	6.46	Inhibition of Aurora B (unknown origin)	35687347
Replicase polyprotein 1ab	IC50	=	490.0	nM	6.31	Inhibition of SARS-CoV-2 Main protease	36169610
HaCaT	IC50	=	700.0	nM	6.16	Antiproliferative (inhibition of cell growth) activity against HaCaT cells (huma...	9371243
HL-60	IC50	=	800.0	nM	6.1	Cytotoxicity in human HL60 cells assessed as reduction in cell viability incubat...	28987605
COP9 signalosome complex subunit 5	IC50	=	910.0	nM	6.04	Inhibition of N-terminal His6-tagged CSN5 (2 to 257 residues) (unknown origin) t...	39129245
HL-60	IC50	=	930.0	nM	6.03	Cytotoxicity in human HL60 cells assessed as reduction in cell viability incubat...	28987605
M-phase inducer phosphatase 2	IC50	=	1000.0	nM	6.0	Inhibition of histidine-tagged human recombinant Cdc25B catalytic domain express...	19028102
HCT-116	IC50	=	1040.0	nM	5.98	Antiproliferative activity against human HCT-116 cells assessed as inhibition of...	39129245
Cytochrome P450 1A2	IC50	=	2160.0	nM	5.67	Inhibition of human recombinant CYP1A2 expressed in HEK293 cells using 3-cyano-7...	30108931
Cytochrome P450 1A2	Ki	=	2220.0	nM	5.65	Inhibition of human recombinant CYP1A2 expressed in HEK293 cells using 3-cyano-7...	30108931
Arachidonate 5-lipoxygenase	IC50	=	3000.0	nM	5.52	5-LO inhibitory activity was determined by inhibition of LTB4 biosynthesis in bo...	9371243
Cytochrome P450 1A1	Ki	=	3660.0	nM	5.44	Inhibition of human recombinant CYP1A1 expressed in HEK293 cells using 7-ethoxyr...	30108931
Cytochrome P450 1A1	IC50	=	3820.0	nM	5.42	Inhibition of human recombinant CYP1A1 expressed in HEK293 cells using 7-ethoxyr...	30108931
HepG2	IC50	=	4970.0	nM	5.3	Antiproliferative activity against human HepG2 cells assessed as inhibition of c...	39129245
Dual specificity protein phosphatase 6	IC50	=	6900.0	nM	5.16	Inhibition of histidine-tagged rat recombinant MKP3 catalytic domain expressed i...	19028102
A-375	IC50	=	8850.0	nM	5.05	Antiproliferative activity against human A-375 cells assessed as inhibition of c...	39129245
Dual specificity protein phosphatase 1	IC50	=	9370.0	nM	5.03	Inhibition of histidine-tagged mouse MKP1 catalytic domain expressed in human He...	19028102

Literature References

PubMed	DOI	Target Context	# Activities
35687347	10.1021/acs.jnatprod.1c01222	HCT-116	6
35687347	10.1021/acs.jnatprod.1c01222	A549	4
30108931	10.1039/C7MD00388A	Cytochrome P450 1A1	4
24984937	10.1016/j.bmc.2014.06.004	No relevant target	4
2558164	10.1021/np50065a012	Unchecked	4
2558164	10.1021/np50065a012	Raji	4
35687347	10.1021/acs.jnatprod.1c01222	Aurora kinase A	4
-	10.1016/j.cropro.2011.09.009	Trichoplusia ni	3
30108931	10.1039/C7MD00388A	Cytochrome P450 1A2	3
28987605	10.1016/j.ejmech.2017.09.027	HL-60	3
30108931	10.1039/C7MD00388A	Cytochrome P450 2C9	2
14980639	10.1016/j.bmcl.2004.01.002	Rattus norvegicus	2
35687347	10.1021/acs.jnatprod.1c01222	Aurora kinase B	2
30108931	10.1039/C7MD00388A	Cytochrome P450 3A4	2
30108931	10.1039/C7MD00388A	Cytochrome P450 2C19	2
39129245	10.1021/acs.jmedchem.4c01514	COP9 signalosome complex subunit 5	2
9371243	10.1021/jm970292n	HaCaT	2
30108931	10.1039/C7MD00388A	Cytochrome P450 2D6	2
30108931	10.1039/C7MD00388A	Cytochrome P450 1B1	2
9371243	10.1021/jm970292n	Molecular identity unknown	2

Data from ChEMBL 36 via Core Engine