Compound Detail

CHEMBL28

APIGENIN

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O=c1cc(-c2ccc(O)cc2)oc2cc(O)cc(O)c12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL28
Name	APIGENIN
Phase	Preclinical
Structure Type	MOL
InChI Key	KZNIFHPLKGYRTM-UHFFFAOYSA-N

106

Targets

240

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

270.2

MW (Da)

2.58

ALogP

HBA

HBD

90.9

PSA (Å²)

0.63

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	3
Heavy Atoms	20
NP-Likeness	1.36

Activity Summary

IC50 190 meas. best 7.92

EC50 23 meas. best 6.8

Ki 23 meas. best 7.19

Kd 4 meas. best 6.6

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Acetylcholinesterase CHEMBL220	IC50	7.92	6.695	12.0	2
Cytochrome P450 1B1 CHEMBL4878	IC50	7.6	7.02	25.0	2
Cytochrome P450 1B1 CHEMBL4878	Ki	7.19	7.19	64.0	1
Estrogen receptor beta CHEMBL242	IC50	6.89	6.89	130.0	1
Dipeptidyl peptidase 4 CHEMBL284	IC50	6.85	6.85	140.0	1
Leishmania amazonensis CHEMBL612877	EC50	6.8	5.944	160.0	5
NCI/ADR-RES CHEMBL613829	IC50	6.7	6.7	200.0	1
Transthyretin CHEMBL3194	Kd	6.6	6.6	250.0	1
MAP kinase-interacting serine/threonine-protein kinase 2 CHEMBL4204	IC50	6.51	6.51	308.0	1
Cytochrome P450 1A1 CHEMBL2231	Ki	6.41	6.41	390.0	1
Cytochrome P450 1A1 CHEMBL2231	IC50	6.37	6.37	427.0	1
Casein kinase 2 CHEMBL3832943	Ki	6.36	6.36	440.0	1
RAW264.7 CHEMBL612557	IC50	6.3	5.1371	500.0	7
Xanthine dehydrogenase/oxidase CHEMBL1929	Ki	6.28	6.28	520.0	1
Amine oxidase [flavin-containing] A CHEMBL1951	IC50	6.19	5.86	640.0	6
Estrogen receptor CHEMBL2304421	Kd	6.18	6.18	660.0	1
Transthyretin CHEMBL3194	IC50	6.18	5.7033	653.0	3
Unchecked CHEMBL612545	IC50	6.18	5.0224	653.0	21
Xanthine dehydrogenase/oxidase CHEMBL1929	IC50	6.16	5.83	700.0	2
17-beta-hydroxysteroid dehydrogenase type 1 CHEMBL3181	IC50	6.15	6.15	710.0	1
Casein kinase II subunit alpha CHEMBL3629	Ki	6.13	6.13	740.0	2
GABA-A receptor; anion channel CHEMBL1907607	Ki	6.11	6.11	770.0	1
Casein kinase II CHEMBL2095191	IC50	6.1	6.1	800.0	2
Cytochrome P450 1A2 CHEMBL3356	IC50	6.1	6.1	795.0	1
Casein kinase II subunit alpha CHEMBL3629	IC50	6.1	6.1	800.0	1
Casein kinase 2 CHEMBL3832943	IC50	6.1	6.1	800.0	1
Casein kinase 2 CHEMBL3988629	IC50	6.1	6.1	800.0	1
Aromatase CHEMBL1978	IC50	6.05	5.702	900.0	5
Pyruvate kinase PKM CHEMBL1075189	IC50	6.0	6.0	990.0	3
MCF7 CHEMBL387	IC50	6.0	5.01	1000.0	2
Proteasome Macropain subunit MB1 CHEMBL4662	IC50	6.0	5.875	1000.0	2
Histone deacetylase 6 CHEMBL1865	IC50	5.99	5.99	1035.0	1
NADPH oxidase 4 CHEMBL1250375	IC50	5.95	5.95	1130.0	1
Amine oxidase [flavin-containing] B CHEMBL2039	IC50	5.95	5.2433	1120.0	3
Monocyte CHEMBL614076	IC50	5.92	5.31	1200.0	2
Estrogen receptor CHEMBL206	IC50	5.9	5.9	1253.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.88	4.6875	1330.0	4
Glycogen synthase kinase-3 CHEMBL2095188	IC50	5.85	5.85	1400.0	1
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	IC50	5.84	5.84	1450.0	1
Human immunodeficiency virus type 1 integrase CHEMBL3471	IC50	5.82	5.82	1500.0	1
Cyclin-dependent kinase 5/CDK5 activator 1 CHEMBL1907600	IC50	5.8	5.8	1600.0	1
Cyclin-dependent kinase 6 CHEMBL2508	IC50	5.77	5.77	1700.0	2
Glycogen synthase kinase-3 beta CHEMBL262	IC50	5.72	5.72	1900.0	1
HT-29 CHEMBL384	IC50	5.7	5.7	2000.0	1
Multidrug resistance-associated protein 1 CHEMBL3004	Ki	5.62	5.465	2400.0	2
Beta-glucuronidase CHEMBL4814	IC50	5.55	5.55	2800.0	1
Poly [ADP-ribose] polymerase tankyrase-2 CHEMBL6154	IC50	5.54	5.535	2900.0	2
GABA-A receptor; anion channel CHEMBL2093872	Ki	5.52	5.52	3019.9	1
Tyrosine-protein kinase SYK CHEMBL2599	EC50	5.52	5.52	3000.0	2
Adenosine receptor A1 CHEMBL318	Ki	5.52	5.52	3000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Ka	1.13	10'5/M	Homo sapiens
Ke	410.0	nM	Homo sapiens
Ke	970.0	nM	Homo sapiens
Ke	410.0	nM	Homo sapiens
T1/2	5.103	hr	Homo sapiens
T1/2	2.0	hr	Mus musculus
T1/2	0.1333	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Acetylcholinesterase	IC50	=	12.0	nM	7.92	Inhibition of AChE (unknown origin)	-
Cytochrome P450 1B1	IC50	=	25.0	nM	7.6	Inhibition of human CYP1B1 by EROD assay	20696580
Cytochrome P450 1B1	Ki	=	64.0	nM	7.19	Inhibition of CYP1B1 EROD activity assessed as inhibition of deethylation of 7-e...	21482471
Estrogen receptor beta	IC50	=	130.0	nM	6.89	Binding affinity towards human estrogen receptor beta (ERbeta)	12824043
Dipeptidyl peptidase 4	IC50	=	140.0	nM	6.85	Inhibition of DPP4 (unknown origin) using Gly-Pro-AMC as substrate preincubated ...	29609120
Leishmania amazonensis	EC50	=	160.0	nM	6.8	Antileishmanial activity against stationary-phase Leishmania amazonensis MHOM/BR...	30095915
NCI/ADR-RES	IC50	=	200.0	nM	6.7	Cytotoxicity against human MCF7ADR cells	37847948
Transthyretin	Kd	=	250.0	nM	6.6	Binding affinity to TTR (unknown origin) by isothermal titration calorimetric an...	26214366
MAP kinase-interacting serine/threonine-protein kinase 2	IC50	=	308.0	nM	6.51	Inhibition of N-terminal GST-tagged recombinant human full length MNK2 expressed...	33026809
Cytochrome P450 1B1	IC50	=	360.0	nM	6.44	Inhibition of recombinant human CYP1B1 expressed in supersomes using ethoxyresor...	28458135
Cytochrome P450 1A1	Ki	=	390.0	nM	6.41	Inhibition of CYP1A1 EROD activity assessed as inhibition of deethylation of 7-e...	21482471
Cytochrome P450 1A1	IC50	=	427.0	nM	6.37	Inhibition of human CYP1A1 by EROD assay	20696580
Casein kinase 2	Ki	=	440.0	nM	6.36	Binding affinity to CK2 (unknown origin)	36745746
RAW264.7	IC50	=	500.0	nM	6.3	Inhibition of COX2 protein expression in mouse RAW264.7 cells	16038536
Xanthine dehydrogenase/oxidase	Ki	=	520.0	nM	6.28	Inhibition of xanthine oxidase (unknown origin)	25019478
Amine oxidase [flavin-containing] A	IC50	=	640.0	nM	6.19	Inhibition of recombinant human MAO-A assessed as reduction in 4-hydroxyquinolin...	27754693
Transthyretin	IC50	=	653.0	nM	6.18	Fluorescence Polarization Binding Assay: Table 3: The FP assay was then adapted ...	-
Estrogen receptor	Kd	=	660.0	nM	6.18	Displacement of [3H]-estradiol (E2) from sheep uterine estrogen receptor	14761204
Transthyretin	IC50	=	653.0	nM	6.18	FP Assay: The FP assay was then adapted for HTS and used to screen ~120,000 smal...	-
Unchecked	IC50	=	653.0	nM	6.18	The FP assay: The FP assay was then adapted for HTS and used to screen a 120,00...	-

Literature References

PubMed	DOI	Target Context	# Activities
25768915	10.1021/acs.jnatprod.5b00011	Leishmania amazonensis	23
30095915	10.1021/acs.jnatprod.8b00356	Leishmania amazonensis	13
3069957	10.1021/np50060a006	Salmonella typhimurium	12
26517554	10.1021/acs.jnatprod.5b00075	ADMET	10
31176093	10.1016/j.ejmech.2019.05.083	Mus musculus	10
28128562	10.1021/acs.jnatprod.6b00643	Amyloid-beta precursor protein	8
-	10.1039/C5MD00142K	Insulin receptor	8
26529431	10.1021/acs.jnatprod.5b00616	Aldo-keto reductase family 1 member B10	7
31465218	10.1021/acs.jnatprod.9b00113	RAW264.7	7
17624791	10.1016/j.bmc.2007.06.046	Unchecked	7
19734910	10.1038/nchembio.215	Plasmodium falciparum	6
30095915	10.1021/acs.jnatprod.8b00356	Mus musculus	6
12816539	10.1042/bj20030674	Unchecked	6
18682327	10.1016/j.bmc.2008.07.052	Prenyltransferase homolog	6
24368208	10.1016/j.ejmech.2013.11.030	Seed linoleate 13S-lipoxygenase-1	6
16441060	10.1021/np050229y	Unchecked	5
21824690	10.1016/j.ejmech.2011.07.031	HepG2	5
24837156	10.1016/j.bmc.2014.04.043	NON-PROTEIN TARGET	5
31465218	10.1021/acs.jnatprod.9b00113	MDA-MB-231	5
32155073	10.1021/acs.jnatprod.9b00922	PBMC	5

Data from ChEMBL 36 via Core Engine