Compound Detail

CHEMBL289277

EMODIN

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Cc1cc(O)c2c(c1)C(=O)c1cc(O)cc(O)c1C2=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL289277
Name	EMODIN
Phase	Preclinical
Structure Type	MOL
InChI Key	RHMXXJGYXNZAPX-UHFFFAOYSA-N

Targets

105

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

270.2

MW (Da)

1.89

ALogP

HBA

HBD

94.8

PSA (Å²)

0.58

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	C15H10O5
MW	270.24
Aromatic Rings	2
Heavy Atoms	20
NP-Likeness	1.19

Activity Summary

IC50 87 meas. best 6.62

Ki 10 meas. best 6.11

EC50 8 meas. best 5.82

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Proteasome component C5 CHEMBL4208	IC50	6.62	6.62	240.0	1
Casein kinase II alpha/beta CHEMBL3038477	IC50	6.34	6.29	460.0	2
Casein kinase II CHEMBL2095191	IC50	6.24	6.045	580.0	4
Estrogen receptor CHEMBL206	Ki	6.11	6.11	770.0	1
Unchecked CHEMBL612545	Ki	6.1	5.495	790.0	2
Casein kinase II subunit alpha CHEMBL3629	IC50	6.05	5.875	890.0	2
Unchecked CHEMBL612545	IC50	6.05	5.0206	890.0	17
Histone deacetylase 6 CHEMBL1865	IC50	5.97	5.97	1076.0	1
Proteasome Macropain subunit MB1 CHEMBL4662	IC50	5.91	5.91	1220.0	1
HEK293 CHEMBL614818	IC50	5.89	5.89	1300.0	1
AGS CHEMBL613860	EC50	5.82	5.82	1500.0	1
Estrogen receptor beta CHEMBL242	Ki	5.82	5.82	1500.0	1
Casein kinase II subunit alpha CHEMBL3629	Ki	5.82	5.775	1500.0	2
T-24 CHEMBL614774	EC50	5.77	5.77	1700.0	1
HepG2 CHEMBL395	IC50	5.77	5.0475	1700.0	4
Casein kinase 2 CHEMBL3832943	Ki	5.73	5.725	1850.0	2
Casein kinase 2 CHEMBL3832943	IC50	5.7	5.7	2000.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.7	4.8875	2020.0	4
Aldo-keto reductase family 1 member B1 CHEMBL1900	Ki	5.67	5.67	2113.0	1
SARS-CoV-2 CHEMBL4303835	EC50	5.66	5.3033	2210.0	3
Serine/threonine-protein kinase pim-1 CHEMBL2147	IC50	5.6	5.6	2500.0	1
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	5.57	5.57	2690.0	1
Estrogen receptor CHEMBL206	IC50	5.57	5.57	2700.0	1
A549 CHEMBL392	EC50	5.54	5.13	2900.0	2
Zika virus CHEMBL4296612	IC50	5.5	5.5	3200.0	1
Amine oxidase [flavin-containing] B CHEMBL2039	IC50	5.49	5.49	3240.0	1
Protein tyrosine phosphatase type IVA 3 CHEMBL4162	IC50	5.46	4.8233	3500.0	3
Cytochrome P450 1B1 CHEMBL4878	IC50	5.43	5.43	3730.0	1
Cytochrome P450 1A2 CHEMBL3356	IC50	5.43	5.43	3730.0	1
HCT-116 CHEMBL394	IC50	5.42	5.2875	3800.0	4
Amine oxidase [flavin-containing] A CHEMBL1951	IC50	5.37	5.37	4320.0	1
Alpha-ketoglutarate-dependent dioxygenase FTO CHEMBL2331065	IC50	5.34	5.34	4530.0	1
Estrogen receptor beta CHEMBL242	IC50	5.28	5.28	5200.0	1
SGC-7901 CHEMBL614909	IC50	5.25	4.73	5600.0	2
Calu-1 CHEMBL613505	IC50	5.2	5.2	6250.0	1
DNA CHEMBL3140325	Ki	5.17	5.17	6800.0	1
dengue virus type 2 CHEMBL613966	EC50	4.96	4.96	10900.0	1
Cytochrome P450 1A1 CHEMBL2231	IC50	4.91	4.91	12200.0	2
Plasmodium falciparum CHEMBL364	IC50	4.9	4.9	12589.2	3
HeLa CHEMBL399	IC50	4.81	4.81	15600.0	1
Genome polyprotein CHEMBL3308998	IC50	4.77	4.435	16870.0	2
Accessory gene regulator protein A CHEMBL1681616	IC50	4.77	4.77	17100.0	1
Echinochloa crus-galli CHEMBL612343	IC50	4.7	4.7	20000.0	1
Proteasome Macropain subunit CHEMBL3492	IC50	4.68	4.68	20850.0	1
LoVo CHEMBL614721	IC50	4.57	4.57	27000.0	1
A549 CHEMBL392	IC50	4.55	4.55	28000.0	1
WISH CHEMBL612811	IC50	4.54	4.54	28800.0	1
Tissue alpha-L-fucosidase CHEMBL3545	IC50	4.5	4.5	32000.0	1
SK-MEL-28 CHEMBL614919	IC50	4.46	4.46	35000.0	1
PC-3 CHEMBL390	IC50	4.46	4.46	35000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Proteasome component C5	IC50	=	240.0	nM	6.62	Inhibition of caspase-like activity of human 26S proteasome assessed as decrease...	30776692
Casein kinase II alpha/beta	IC50	=	460.0	nM	6.34	Inhibition of human CSNK2A1/2B expressed in Escherichia coli BL21(DE3) using RRR...	22377675
Casein kinase II alpha/beta	IC50	=	580.0	nM	6.24	Inhibition of human CK2-alpha/beta expressed in Escherichia coli BL21(DE3) using...	29288942
Casein kinase II	IC50	=	580.0	nM	6.24	Inhibition of human recombinant CK2a1/CK2b holoenzyme expressed in Escherichia c...	25272055
Casein kinase II	IC50	=	580.0	nM	6.24	Inhibition of human recombinant CK2 expressed in Escherichia coli BL21(DE3) usin...	23711832
Estrogen receptor	Ki	=	770.0	nM	6.11	Inhibition of binding of 17 beta-estradiol to human Estrogen receptor alpha	11459643
Unchecked	Ki	=	790.0	nM	6.1	Non-competitive inhibition of human alpha-glucosidase expressed in Saccharomyces...	27933892
Unchecked	IC50	=	890.0	nM	6.05	Inhibition of rat liver casein kinase-2 preincubated for 5 mins prior ATP additi...	22377675
Casein kinase II subunit alpha	IC50	=	890.0	nM	6.05	Inhibition of Zea mays CK2alpha	12816539
Unchecked	IC50	=	890.0	nM	6.05	Inhibition of wild-type CK2 holoenzyme	12816539
Casein kinase II	IC50	=	1000.0	nM	6.0	Inhibition of CK2 (unknown origin) using REEETEEE as substrate after 15 mins in ...	-
Histone deacetylase 6	IC50	=	1076.0	nM	5.97	Determination of IC50 values for inhibition of enzymatic assay of human HDAC6 wi...	-
Unchecked	IC50	=	1100.0	nM	5.96	Inhibition of tau K19 (unknown origin) aggregation assessed as inhibition of pai...	23484434
Proteasome Macropain subunit MB1	IC50	=	1220.0	nM	5.91	Inhibition of chymotrypsin-like activity of human 26S proteasome assessed as dec...	30776692
HEK293	IC50	=	1300.0	nM	5.89	Cytotoxicity against human HEK293 cells after 2 days by alamar blue assay	22093761
Estrogen receptor beta	Ki	=	1500.0	nM	5.82	Inhibition of binding of 17 beta-estradiol to human Estrogen receptor beta	11459643
AGS	EC50	=	1500.0	nM	5.82	Phototoxicity against human AGS cells assessed as reduction in cell growth prein...	37708055
Casein kinase II subunit alpha	Ki	=	1500.0	nM	5.82	Inhibition of CK2alpha (unknown origin)	31400711
T-24	EC50	=	1700.0	nM	5.77	Phototoxicity against human T24 cells assessed as reduction in cell growth prein...	37708055
HepG2	IC50	=	1700.0	nM	5.77	Cytotoxicity against human HepG2 cells after 6 days by MTT assay	29786436

Literature References

PubMed	DOI	Target Context	# Activities
36064125	10.1016/j.bmcl.2022.128974	Unchecked	11
17220400	10.1128/aac.00999-06	Streptococcus mutans	9
22137788	10.1016/j.bmcl.2011.11.008	Protein tyrosine phosphatase type IVA 3	9
23534483	10.1021/jm301816a	Bacillus subtilis	7
8350094	10.1021/np50096a018	Platelet	7
22212721	10.1016/j.bmcl.2011.12.044	HCT-116	7
38864383	10.1021/acs.jmedchem.4c00597	SARS-CoV-2	6
11374975	10.1021/np000569d	HeLa	6
11374975	10.1021/np000569d	Vero	6
12816539	10.1042/bj20030674	Unchecked	6
11374975	10.1021/np000569d	WISH	6
11374975	10.1021/np000569d	K562	6
11374975	10.1021/np000569d	Calu-1	6
11374975	10.1021/np000569d	Raji	6
1479375	10.1021/np50089a001	NON-PROTEIN TARGET	6
18556196	10.1016/j.bmcl.2008.05.109	Unchecked	5
11459643	10.1016/s0960-894x(01)00318-3	Estrogen receptor	5
27140653	10.1021/acs.jnatprod.6b00185	Mus musculus	5
34812616	10.1021/acs.jmedchem.1c01547	Unchecked	5
23534483	10.1021/jm301816a	Staphylococcus aureus	5

Data from ChEMBL 36 via Core Engine