Compound Detail

CHEMBL151

LUTEOLIN

🧪 Phase II

Enter ChEMBL ID:

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

Research home View demo workspace

🧪 Phase II

O=c1cc(-c2ccc(O)c(O)c2)oc2cc(O)cc(O)c12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL151
Name	LUTEOLIN
Phase	Phase II
Structure Type	MOL
InChI Key	IQPNAANSBPBGFQ-UHFFFAOYSA-N

Known Names

Cyanidenon-1470 Digitoflavone Flacitran Luteolin Luteoline Luteolol Salifazide Weld lake Yama kariyasu

139

Targets

283

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

286.2

MW (Da)

2.28

ALogP

HBA

HBD

111.1

PSA (Å²)

0.51

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

Extended Properties

Molecular Formula	C15H10O6
MW	286.24
Aromatic Rings	3
Heavy Atoms	21
NP-Likeness	1.50

Activity Summary

IC50 227 meas. best 7.14

Ki 28 meas. best 8.4

EC50 25 meas. best 5.84

Kd 3 meas. best 7.16

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	Ki	8.4	6.92	4.0	3
Carbonic anhydrase 7 CHEMBL2326	Ki	8.33	8.33	4.7	1
Cytochrome P450 1B1 CHEMBL4878	Ki	7.25	7.25	56.0	1
Carbonic anhydrase 12 CHEMBL3242	Ki	7.22	7.22	60.3	1
Transthyretin CHEMBL3194	Kd	7.16	7.16	70.0	1
Unchecked CHEMBL612545	IC50	7.14	5.1636	72.0	33
Cytochrome P450 1B1 CHEMBL4878	IC50	7.1	6.77	79.0	2
Dipeptidyl peptidase 4 CHEMBL284	IC50	6.92	6.92	120.0	1
MAP kinase-interacting serine/threonine-protein kinase 1 CHEMBL4718	IC50	6.75	6.75	179.0	1
RAW264.7 CHEMBL612557	IC50	6.68	5.224	210.0	15
Casein kinase 2 CHEMBL3832943	Ki	6.62	6.62	240.0	1
Carbonic anhydrase 4 CHEMBL3729	Ki	6.53	6.53	293.0	1
Monocarboxylate transporter 1 CHEMBL4360	IC50	6.39	6.39	410.0	1
Human immunodeficiency virus type 1 integrase CHEMBL3471	IC50	6.35	5.12	450.0	4
Casein kinase 2 CHEMBL3832943	IC50	6.3	6.3	500.0	1
Casein kinase 2 CHEMBL3988629	IC50	6.3	6.3	500.0	1
Beta-secretase 1 CHEMBL4822	IC50	6.28	6.28	520.0	1
Xanthine dehydrogenase/oxidase CHEMBL1929	IC50	6.26	5.4367	550.0	3
MAP kinase-interacting serine/threonine-protein kinase 2 CHEMBL4204	IC50	6.24	6.24	579.0	1
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	6.22	5.86	600.0	2
DNA topoisomerase 1 CHEMBL1075164	IC50	6.18	5.74	660.0	2
Aldo-keto reductase family 1 member B1 CHEMBL3081	IC50	6.12	5.57	754.0	2
Glycogen synthase kinase-3 CHEMBL2095188	IC50	6.1	6.1	800.0	1
3-oxoacyl-acyl-carrier protein reductase CHEMBL4513	Ki	6.1	5.925	800.0	2
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	IC50	6.08	6.08	830.0	1
NADPH oxidase 4 CHEMBL1250375	IC50	6.07	6.07	850.0	1
Cytochrome P450 1A1 CHEMBL2231	Ki	6.05	5.835	890.0	2
Neutrophil CHEMBL613710	IC50	6.05	5.4586	900.0	7
Macrophage metalloelastase CHEMBL4393	IC50	6.01	6.01	980.0	1
Casein kinase II alpha'/ beta CHEMBL3883328	IC50	6.0	6.0	1000.0	1
Poly [ADP-ribose] polymerase tankyrase-2 CHEMBL6154	IC50	5.97	5.965	1071.5	2
Hepatitis C virus CHEMBL379	IC50	5.95	5.95	1120.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.95	5.48	1130.0	3
Aromatase CHEMBL1978	IC50	5.92	5.92	1199.5	1
Cytochrome P450 1A1 CHEMBL2231	IC50	5.9	5.9	1249.0	1
Inositol hexakisphosphate kinase 2 CHEMBL4523488	IC50	5.89	5.89	1300.0	1
Proteasome Macropain subunit MB1 CHEMBL4662	IC50	5.89	5.855	1300.0	2
Histone deacetylase 6 CHEMBL1865	IC50	5.84	5.84	1438.0	1
Sodium-dependent dopamine transporter CHEMBL338	EC50	5.84	5.84	1450.0	1
Glycogen synthase kinase-3 beta CHEMBL262	IC50	5.82	5.82	1500.0	1
Unchecked CHEMBL612545	Kd	5.82	5.82	1520.0	1
Monocyte CHEMBL614076	IC50	5.82	5.82	1500.0	1
Aldo-keto reductase family 1 member B1 CHEMBL2622	IC50	5.81	5.81	1540.0	1
Adenosine receptor A1 CHEMBL318	Ki	5.81	5.795	1550.0	2
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	5.8	5.8	1600.0	1
NAD-dependent protein deacylase sirtuin-6 CHEMBL2163182	IC50	5.72	5.72	1900.0	1
Xanthine dehydrogenase/oxidase CHEMBL3649	Ki	5.72	5.72	1900.0	1
Enoyl-acyl-carrier protein reductase CHEMBL4150	IC50	5.7	5.7	2000.0	2
Enoyl-acyl-carrier protein reductase CHEMBL4150	Ki	5.68	5.68	2100.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL2459	EC50	5.64	5.64	2300.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	7600.0	ng.hr.mL-1	Rattus norvegicus
AUC	8180.0	ng.hr.mL-1	Rattus norvegicus
AUC	11400.0	ng.hr.mL-1	Rattus norvegicus
AUC	12500.0	ng.hr.mL-1	Rattus norvegicus
CL	13.35	mL.min-1.kg-1	Rattus norvegicus
CL	8.95	mL.min-1.kg-1	Rattus norvegicus
Ka	1.33	10'5/M	Homo sapiens
MRT	1.41	hr	Rattus norvegicus
MRT	2.32	hr	Rattus norvegicus
MRT	1.65	hr	Rattus norvegicus
MRT	2.68	hr	Rattus norvegicus
T1/2	3.2	hr	Rattus norvegicus
T1/2	3.31	hr	Rattus norvegicus
T1/2	0.1833	hr	Homo sapiens
T1/2	2.0	hr	Mus musculus
T1/2	1.0	hr	Mus musculus
T1/2	2.0	hr	Mus musculus
T1/2	1.0	hr	Mus musculus
Vd	3.74	L.kg-1	Rattus norvegicus
Vd	2.57	L.kg-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	Ki	=	4.0	nM	8.4	Binding affinity to human MAPK/ERK signalling assessed as inhibition constant	38295689
Carbonic anhydrase 7	Ki	=	4.7	nM	8.33	Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins at...	26498393
Cytochrome P450 1B1	Ki	=	56.0	nM	7.25	Inhibition of CYP1B1 EROD activity assessed as inhibition of deethylation of 7-e...	21482471
Carbonic anhydrase 12	Ki	=	60.3	nM	7.22	Inhibition of human recombinant carbonic anhydrase 12 preincubated for 15 mins a...	26498393
Transthyretin	Kd	=	70.0	nM	7.16	Binding affinity to TTR (unknown origin) by isothermal titration calorimetric an...	26214366
Unchecked	IC50	=	72.0	nM	7.14	Inhibition of biotinylated 5-(4-((Z)-3-Carboxy-3-hydroxyacryloyl)-4-(4-chloroben...	32883638
Cytochrome P450 1B1	IC50	=	79.0	nM	7.1	Inhibition of human CYP1B1 by EROD assay	20696580
Dipeptidyl peptidase 4	IC50	=	120.0	nM	6.92	Inhibition of DPP4 (unknown origin) using Gly-Pro-AMC as substrate preincubated ...	29609120
MAP kinase-interacting serine/threonine-protein kinase 1	IC50	=	179.0	nM	6.75	Inhibition of GST-tagged recombinant human full length MNK1 expressed in insect ...	33026809
RAW264.7	IC50	=	210.0	nM	6.68	Inhibition of NO production in LPS-stimulated mouse RAW264.7 cells pre-incubated...	25176187
Casein kinase 2	Ki	=	240.0	nM	6.62	Binding affinity to CK2 (unknown origin)	36745746
Carbonic anhydrase 4	Ki	=	293.0	nM	6.53	Inhibition of human recombinant carbonic anhydrase 4	26498393
Unchecked	IC50	=	300.0	nM	6.52	Peroxynitrite scavenging activity assessed as inhibition of DHR oxidation	17624791
Cytochrome P450 1B1	IC50	=	360.0	nM	6.44	Inhibition of recombinant human CYP1B1 expressed in supersomes using ethoxyresor...	28458135
Monocarboxylate transporter 1	IC50	=	410.0	nM	6.39	Inhibition of MCT1 (unknown origin)	38308950
Unchecked	Ki	=	440.0	nM	6.36	Competitive inhibition of Xanthomonas oryzae pv. Oryzae KS-1-21 GlmU using 0.25 ...	22521370
Human immunodeficiency virus type 1 integrase	IC50	=	450.0	nM	6.35	Inhibition of His6-tagged HIV-1 integrase assessed as decrease in integrase-Flag...	24794743
Casein kinase 2	IC50	=	500.0	nM	6.3	Inhibition of rat liver CK2 phosphorylation using RRRADDSDDDDD as substrate in p...	36745746
Casein kinase 2	IC50	=	500.0	nM	6.3	Inhibition of human recombinant CK2 expressed in Escherichia coli using RRRADDSD...	30733087
Beta-secretase 1	IC50	=	520.0	nM	6.28	Inhibition of BACE1 (unknown origin)	33984802

Literature References

PubMed	DOI	Target Context	# Activities
-	10.1584/jpestics.G10-24	Spodoptera exigua	44
9287421	10.1021/np970011e	Aorta	17
19388706	10.1021/np8007123	Xanthine dehydrogenase/oxidase	17
-	10.1007/s00044-012-0449-4	Mus musculus	15
21209248	10.1124/dmd.110.037333	Rattus norvegicus	14
21899269	10.1021/np2003935	Mus musculus	14
23411073	10.1016/j.bmcl.2013.01.049	MV4-11	13
29887353	10.1016/j.bmcl.2018.05.051	B16	12
12951092	10.1016/s0960-894x(03)00710-8	RBL-2H3	11
26517554	10.1021/acs.jnatprod.5b00075	ADMET	10
9287421	10.1021/np970011e	Platelet	10
23786520	10.1021/np400224w	Cytochrome b-245 heavy chain	9
21209248	10.1124/dmd.110.037333	ADMET	9
25987378	10.1016/j.bmcl.2015.04.052	Molecular identity unknown	9
24900447	10.1021/ml2003058	G-protein coupled receptor 35	8
31427220	10.1016/j.bmcl.2019.07.048	Nakaseomyces glabratus	8
17624791	10.1016/j.bmc.2007.06.046	Unchecked	7
25151578	10.1016/j.ejmech.2014.08.035	Neutrophil	7
17411092	10.1021/np060609z	DNA topoisomerase 2-alpha	6
20189399	10.1016/j.bmc.2010.01.046	Tyrosinase	6

Data from ChEMBL 36 via Core Engine