Compound Detail

CHEMBL90568

DIOSMETIN

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COc1ccc(-c2cc(=O)c3c(O)cc(O)cc3o2)cc1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL90568
Name	DIOSMETIN
Phase	Preclinical
Structure Type	MOL
InChI Key	MBNGWHIJMBWFHU-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

300.3

MW (Da)

2.59

ALogP

HBA

HBD

100.1

PSA (Å²)

0.67

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	C16H12O6
MW	300.27
Aromatic Rings	3
Heavy Atoms	22
NP-Likeness	1.34

Activity Summary

IC50 25 meas. best 7.54

Ki 3 meas. best 7.8

EC50 2 meas. best 5.1

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cytochrome P450 1B1 CHEMBL4878	Ki	7.8	7.8	16.0	2
Cytochrome P450 1B1 CHEMBL4878	IC50	7.54	7.54	29.0	1
Cytochrome P450 1A1 CHEMBL2231	Ki	7.05	7.05	89.0	1
Cytochrome P450 1A1 CHEMBL2231	IC50	6.85	6.85	140.0	1
Xanthine dehydrogenase/oxidase CHEMBL1929	IC50	6.28	6.28	530.0	1
Histone deacetylase 6 CHEMBL1865	IC50	6.28	6.28	528.1	1
Neutrophil CHEMBL613710	IC50	6.16	5.3525	700.0	4
Inositol hexakisphosphate kinase 2 CHEMBL4523488	IC50	6.05	6.05	900.0	1
Cytochrome P450 1A2 CHEMBL3356	IC50	5.61	5.61	2437.0	1
Multidrug resistance-associated protein 1 CHEMBL3004	IC50	5.52	5.52	3000.0	1
Monocyte CHEMBL614076	IC50	5.52	5.52	3000.0	1
KBM5 CHEMBL4483250	IC50	5.19	5.13	6460.0	2
Inositol polyphosphate multikinase CHEMBL4523401	IC50	5.14	5.14	7200.0	1
Unchecked CHEMBL612545	IC50	5.12	4.725	7600.0	2
HepG2 CHEMBL395	EC50	5.1	5.1	7980.0	1
K562 CHEMBL385	IC50	5.08	5.08	8420.0	1
RAW264.7 CHEMBL612557	IC50	5.08	4.7025	8400.0	4
Peritoneal macrophage CHEMBL5314330	IC50	5.05	5.05	8900.0	1
Lysine-specific histone demethylase 1A CHEMBL6136	IC50	4.55	4.55	27900.0	1
HT-22 CHEMBL614316	EC50	4.22	4.22	59700.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	427.0	ng.hr.mL-1	Rattus norvegicus
AUC	466.0	ng.hr.mL-1	Rattus norvegicus
CL	238.33	mL.min-1.kg-1	Rattus norvegicus
Cmax	1864.99	nM	Rattus norvegicus
MRT	0.597	hr	Rattus norvegicus
MRT	0.767	hr	Rattus norvegicus
T1/2	0.514	hr	Rattus norvegicus
Vd	10.3	L.kg-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cytochrome P450 1B1	Ki	=	16.0	nM	7.8	Inhibition of CYP1B1 (unknown origin)	28458135
Cytochrome P450 1B1	Ki	=	16.0	nM	7.8	Inhibition of CYP1B1 EROD activity assessed as inhibition of deethylation of 7-e...	21482471
Cytochrome P450 1B1	IC50	=	29.0	nM	7.54	Inhibition of human CYP1B1 by EROD assay	20696580
Cytochrome P450 1A1	Ki	=	89.0	nM	7.05	Inhibition of CYP1A1 EROD activity assessed as inhibition of deethylation of 7-e...	21482471
Cytochrome P450 1A1	IC50	=	140.0	nM	6.85	Inhibition of human CYP1A1 by EROD assay	20696580
Histone deacetylase 6	IC50	=	528.1	nM	6.28	Determination of IC50 values for inhibition of enzymatic assay of human HDAC6 wi...	-
Xanthine dehydrogenase/oxidase	IC50	=	530.0	nM	6.28	Inhibition of XO (unknown origin) using xanthine as substrate assessed as reduct...	37908076
Neutrophil	IC50	=	700.0	nM	6.16	Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as in...	23871908
Inositol hexakisphosphate kinase 2	IC50	=	900.0	nM	6.05	Inhibition of human IP6K2 using insP6 as substrate preincubated for 15 mins foll...	30624931
Cytochrome P450 1A2	IC50	=	2437.0	nM	5.61	Inhibition of human CYP1A2 by EROD assay	20696580
Monocyte	IC50	=	3000.0	nM	5.52	Inhibition of procoagulant activity in monocyte from human blood assessed as cou...	8882428
Multidrug resistance-associated protein 1	IC50	=	3000.0	nM	5.52	Inhibition of MRP1	19725578
Neutrophil	IC50	=	3600.0	nM	5.44	Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as in...	23871908
KBM5	IC50	=	6460.0	nM	5.19	Antiproliferative activity against human KBM5 cells harbouring T315I mutant asse...	35551036
Inositol polyphosphate multikinase	IC50	=	7200.0	nM	5.14	Inhibition of human IPMK using insP3 as substrate preincubated for 15 mins follo...	30624931
Unchecked	IC50	=	7600.0	nM	5.12	Inhibition of NADPH oxidase in Homo sapiens (human) HUVEC cells	-
HepG2	EC50	=	7980.0	nM	5.1	Antioxidant activity in human HepG2 cells assessed as decrease in fluorescence l...	26974372
K562	IC50	=	8420.0	nM	5.08	Antiproliferative activity against human K562 cells assessed as cell growth inhi...	35551036
RAW264.7	IC50	=	8400.0	nM	5.08	Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed a...	31747281
KBM5	IC50	=	8520.0	nM	5.07	Antiproliferative activity against human KBM5 cells assessed as cell growth inhi...	35551036

Literature References

PubMed	DOI	Target Context	# Activities
21209248	10.1124/dmd.110.037333	Catechol O-methyltransferase	15
26517554	10.1021/acs.jnatprod.5b00075	ADMET	10
36731248	10.1016/j.bmc.2023.117187	Staphylococcus aureus	9
21209248	10.1124/dmd.110.037333	Rattus norvegicus	8
25190466	10.1016/j.bmcl.2014.07.093	Nuclear factor NF-kappa-B complex	7
30624931	10.1021/acs.jmedchem.8b01593	Inositol hexakisphosphate kinase 2	6
18249545	10.1016/j.bmc.2008.01.028	No relevant target	5
30624931	10.1021/acs.jmedchem.8b01593	Inositol polyphosphate multikinase	5
18249545	10.1016/j.bmc.2008.01.028	Caco-2	5
21209248	10.1124/dmd.110.037333	ADMET	5
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
-	10.6019/CHEMBL4808148	Histone deacetylase 6	4
23871908	10.1016/j.ejmech.2013.06.019	Neutrophil	4
31176093	10.1016/j.ejmech.2019.05.083	Tyrosine-protein phosphatase non-receptor type 1	3
31176093	10.1016/j.ejmech.2019.05.083	Unchecked	3
26517554	10.1021/acs.jnatprod.5b00075	Unchecked	3
19807106	10.1021/jm900964r	Peroxisome proliferator-activated receptor alpha	2
18507367	10.1021/jm800115x	Alpha-amylase 1A	2
21482471	10.1016/j.bmc.2011.03.042	Cytochrome P450 1A1	2
26974372	10.1016/j.ejmech.2016.02.045	HepG2	2

Data from ChEMBL 36 via Core Engine