Compound Detail

CHEMBL164

MYRICETIN

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O=c1c(O)c(-c2cc(O)c(O)c(O)c2)oc2cc(O)cc(O)c12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL164
Name	MYRICETIN
Phase	Preclinical
Structure Type	MOL
InChI Key	IKMDFBPHZNJCSN-UHFFFAOYSA-N

Targets

198

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

318.2

MW (Da)

1.69

ALogP

HBA

HBD

151.6

PSA (Å²)

0.37

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	C15H10O8
MW	318.24
Aromatic Rings	3
Heavy Atoms	23
NP-Likeness	1.70

Activity Summary

IC50 154 meas. best 7.92

Ki 22 meas. best 7.57

EC50 19 meas. best 9.29

Kd 3 meas. best 9.6

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Muscleblind-like protein 1 CHEMBL1293317	Kd	9.6	9.6	0.2	1
Pyruvate kinase PKM CHEMBL1075189	EC50	9.29	9.29	0.5	1
Acetylcholinesterase CHEMBL220	IC50	7.92	7.92	12.0	1
Cytochrome P450 1B1 CHEMBL4878	Ki	7.57	7.57	27.0	2
Unchecked CHEMBL612545	IC50	7.46	5.6472	35.0	32
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform CHEMBL4005	Kd	6.77	6.77	170.0	1
Unchecked CHEMBL612545	Kd	6.77	6.77	170.0	1
Replicase polyprotein 1ab CHEMBL4523582	IC50	6.7	6.265	200.0	8
Alpha-synuclein CHEMBL6152	IC50	6.66	5.77	220.0	2
ADMET CHEMBL612558	Ki	6.52	6.035	300.0	2
DNA repair nuclease/redox regulator APEX1 CHEMBL5619	IC50	6.5	6.5	320.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.48	6.48	330.0	1
Cytochrome P450 1A1 CHEMBL2231	Ki	6.43	6.43	370.0	1
DNA topoisomerase 2-alpha CHEMBL1806	IC50	6.41	6.41	390.0	1
Enoyl-acyl-carrier protein reductase CHEMBL4150	IC50	6.4	6.4	400.0	1
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 CHEMBL5925	IC50	6.38	6.38	414.6	1
Lactoylglutathione lyase CHEMBL2424	IC50	6.25	5.99	560.0	3
Unchecked CHEMBL612545	Ki	6.22	5.1117	600.0	6
Human immunodeficiency virus type 1 integrase CHEMBL3471	IC50	6.22	5.66	600.0	4
Inositol hexakisphosphate kinase 2 CHEMBL4523488	IC50	6.16	6.16	700.0	1
Serine/threonine-protein kinase pim-1 CHEMBL2147	IC50	6.11	5.75	780.0	2
Nonstructural protein 3 CHEMBL4523954	Ki	6.1	6.1	800.0	1
Protein E6 CHEMBL2010633	IC50	6.07	6.07	850.0	1
Casein kinase 2 CHEMBL3832943	IC50	6.05	6.05	900.0	1
SARS-CoV-2 CHEMBL4303835	EC50	6.05	5.2357	900.0	7
Casein kinase II CHEMBL2095191	IC50	6.04	6.04	920.0	1
Casein kinase 2 CHEMBL3988629	IC50	6.04	6.04	920.0	1
ELAV-like protein 3 CHEMBL4105924	IC50	6.0	6.0	1000.0	1
Inositol polyphosphate multikinase CHEMBL4523401	IC50	5.96	5.96	1100.0	1
Microtubule-associated protein tau CHEMBL1293224	IC50	5.92	5.92	1200.0	1
Arginase CHEMBL3108635	Ki	5.92	5.92	1200.0	1
Nonstructural protein 3 CHEMBL4523954	IC50	5.89	5.275	1300.0	2
Pancreatic triacylglycerol lipase CHEMBL1812	IC50	5.87	5.87	1340.0	1
Serine/threonine-protein kinase B-raf CHEMBL5145	IC50	5.81	5.81	1562.0	1
Histone deacetylase 6 CHEMBL1865	IC50	5.81	5.81	1562.0	1
Myosin light chain kinase, smooth muscle CHEMBL2428	Ki	5.77	5.77	1700.0	1
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	IC50	5.77	5.77	1690.0	1
Tyrosine-protein kinase transforming protein Fps CHEMBL5708	Ki	5.75	5.75	1800.0	1
Fatty acid synthase CHEMBL4512	IC50	5.7	5.7	2000.0	1
Arginase CHEMBL3108635	IC50	5.68	5.68	2100.0	1
G-protein coupled receptor 35 CHEMBL1293267	IC50	5.67	5.67	2120.0	1
Xanthine dehydrogenase/oxidase CHEMBL1929	IC50	5.62	5.62	2380.0	1
DNA dC->dU-editing enzyme APOBEC-3G CHEMBL1741217	IC50	5.62	5.62	2390.0	1
Multidrug resistance-associated protein 1 CHEMBL3004	Ki	5.62	5.25	2400.0	2
Insulin receptor CHEMBL1981	Ki	5.58	5.58	2600.0	1
Beta-secretase 1 CHEMBL4822	IC50	5.55	5.5075	2800.0	4
Lysine-specific demethylase 4E CHEMBL1293226	IC50	5.52	5.52	3000.0	2
G-protein coupled receptor 35 CHEMBL1293267	EC50	5.52	5.175	3020.0	2
Plasmodium falciparum CHEMBL364	IC50	5.4	5.0038	3981.1	8
Leishmania donovani CHEMBL367	IC50	5.39	5.39	4080.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	99178.15	mL.min-1.g-1	Rattus norvegicus
CL	68132.01	mL.min-1.g-1	Rattus norvegicus
T1/2	0.2338	hr	Rattus norvegicus
T1/2	0.3397	hr	Rattus norvegicus
T1/2	0.001333	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Muscleblind-like protein 1	Kd	=	0.25	nM	9.6	Binding affinity to MBNL1 (unknown origin)	36490325
Pyruvate kinase PKM	EC50	=	0.51	nM	9.29	Activation of recombinant PKM2 (unknown origin) Phe26, Tyr390, Glu397, Asp354, L...	34726055
Acetylcholinesterase	IC50	=	12.0	nM	7.92	Inhibition of AChE (unknown origin)	-
Cytochrome P450 1B1	Ki	=	27.0	nM	7.57	Inhibition of CYP1B1 EROD activity assessed as inhibition of deethylation of 7-e...	21482471
Cytochrome P450 1B1	Ki	=	27.0	nM	7.57	Inhibition of CYP1B1 (unknown origin)	28458135
Unchecked	IC50	=	35.0	nM	7.46	Inhibition of beef heart mitochondrial NADH oxidase assessed per mg of protein	2959755
Unchecked	IC50	=	45.0	nM	7.35	Inhibition of beef heart mitochondrial succinoxidase assessed per mg of protein	2959755
Unchecked	Kd	=	170.0	nM	6.77	Inhibition of PI3K	16441060
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	Kd	=	170.0	nM	6.77	Binding affinity to PI3Kalpha (unknown origin) assessed as dissociation constant	38295689
Replicase polyprotein 1ab	IC50	=	200.0	nM	6.7	Inhibition of SARS-CoV-2 Main protease	36169610
Unchecked	IC50	=	200.0	nM	6.7	Inhibition of beta amyloid (1 to 40) fibril formation	19931462
Alpha-synuclein	IC50	=	220.0	nM	6.66	Inhibition of alpha-synuclein fibril formation (unknown origin) incubated for 24...	30743095
Replicase polyprotein 1ab	IC50	=	220.0	nM	6.66	SARS-CoV-2 3CL-Pro protease inhibition IC50 determined by FRET kind of response ...	-
Unchecked	IC50	=	290.0	nM	6.54	Inhibition of beta amyloid (1 to 40) fibril formation by thioflavin T staining-b...	19931462
ADMET	Ki	=	300.0	nM	6.52	Inhibition of guinea pig aldehyde oxidase	20853847
DNA repair nuclease/redox regulator APEX1	IC50	=	320.0	nM	6.5	Inhibition of human APE1 preincubated for 15 mins followed by substrate addition...	28161249
DNA repair nuclease/redox regulator APEX1	IC50	=	320.0	nM	6.5	Inhibition of human APE1 after 25 mins by fluorescence assay	25280182
NON-PROTEIN TARGET	IC50	=	330.0	nM	6.48	Antioxidant activity assessed as superoxide-scavenging activity by nitrite metho...	9461655
Unchecked	IC50	=	340.0	nM	6.47	Inhibition of beta amyloid (1 to 42) fibril formation	19931462
Unchecked	IC50	=	370.0	nM	6.43	Inhibition of rat liver mitochondrial ATPase assessed per mg of protein	2959755

Literature References

PubMed	DOI	Target Context	# Activities
-	10.1007/s00044-009-9190-z	NON-PROTEIN TARGET	28
31022552	10.1016/j.ejmech.2019.04.031	ADMET	22
27374242	10.1016/j.bmcl.2016.06.054	RAW264.7	20
17851081	10.1016/j.bmc.2007.07.057	Unchecked	11
19931462	10.1016/j.bmc.2009.10.063	Unchecked	10
26517554	10.1021/acs.jnatprod.5b00075	ADMET	10
22212721	10.1016/j.bmcl.2011.12.044	HCT-116	7
16441060	10.1021/np050229y	Unchecked	7
31427220	10.1016/j.bmcl.2019.07.048	Nakaseomyces glabratus	7
24900447	10.1021/ml2003058	G-protein coupled receptor 35	7
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	6
24749980	10.1021/np400781y	Escherichia coli	6
19734910	10.1038/nchembio.215	Plasmodium falciparum	6
2959755	10.1021/np50051a014	Unchecked	6
21824690	10.1016/j.ejmech.2011.07.031	HepG2	6
31427220	10.1016/j.bmcl.2019.07.048	Candida albicans	5
27623545	10.1016/j.bmcl.2016.08.094	NON-PROTEIN TARGET	5
22578462	10.1016/j.bmcl.2012.04.081	Unchecked	5
22789812	10.1016/j.ejmech.2012.06.031	CWR22R	5
9287415	10.1021/np960581z	L929	5

Data from ChEMBL 36 via Core Engine