Compound Detail

CHEMBL44

GENISTEIN

🧪 Phase II

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🧪 Phase II

O=c1c(-c2ccc(O)cc2)coc2cc(O)cc(O)c12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL44
Name	GENISTEIN
Phase	Phase II
Structure Type	MOL
InChI Key	TZBJGXHYKVUXJN-UHFFFAOYSA-N

Known Names

(-)-.alpha.-isosparteine .alpha.-isospartein .alpha.-isosparteine .alpha.-isosparteine, (-)- .alpha.-sparteine 11-isosparteine 4',5,7-trihydroxyisoflavone BIO 300 BIO-300 Bonistein FW-635I-2 Genistein +10 more

123

Targets

295

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

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
Chirality	Achiral

Flags

Natural Product

USAN Year

2019

Extended Properties

Molecular Formula	C15H10O5
MW	270.24
Aromatic Rings	3
Heavy Atoms	20
NP-Likeness	1.35

Indications

Breast Neoplasms Coronary Disease Metabolic Syndrome Osteoporosis Pancreatic Neoplasms Post-Acute COVID-19 Syndrome Prostatic Neoplasms Prostatic Neoplasms, Castration-Resistant Pulmonary Fibrosis Severe Acute Respiratory Syndrome Urinary Bladder Neoplasms Urinary Bladder Neoplasms Carcinoma, Non-Small-Cell Lung Colonic Neoplasms Colorectal Neoplasms Cystic Fibrosis Neoplasms Rectal Neoplasms

Activity Summary

IC50 229 meas. best 8.89

EC50 37 meas. best 8.77

Ki 24 meas. best 9.23

Kd 5 meas. best 5.03

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Estrogen receptor beta CHEMBL242	Ki	9.23	8.425	0.6	2
Estrogen receptor beta CHEMBL242	IC50	8.89	7.4527	1.3	22
Estrogen receptor beta CHEMBL242	EC50	8.77	7.581	1.7	10
Aldehyde oxidase CHEMBL3257	IC50	8.3	7.385	5.0	2
Estrogen receptor CHEMBL206	IC50	8.01	6.1673	9.7	22
Steroid hormone receptor ERR1 CHEMBL3429	IC50	8.0	8.0	10.0	1
Estrogen receptor CHEMBL206	EC50	7.7	6.4943	20.0	7
NON-PROTEIN TARGET CHEMBL3879801	EC50	7.55	4.9775	28.0	4
Estrogen receptor CHEMBL206	Ki	7.41	6.92	39.0	2
MCF7 CHEMBL387	IC50	7.3	5.2317	50.0	6
Sulfotransferase 1A1 CHEMBL4886	IC50	6.54	6.54	290.0	1
Unchecked CHEMBL612545	IC50	6.44	4.7677	365.0	22
Dual specificity mitogen-activated protein kinase kinase 4 CHEMBL2897	IC50	6.4	6.4	400.0	1
Steroid hormone receptor ERR2 CHEMBL3751	IC50	6.4	6.4	395.0	1
Dipeptidyl peptidase 4 CHEMBL284	IC50	6.32	6.32	480.0	1
Ishikawa CHEMBL614649	IC50	6.29	6.29	510.0	1
Epidermal growth factor receptor CHEMBL203	IC50	6.22	5.7333	600.0	6
Amine oxidase [flavin-containing] B CHEMBL2039	IC50	6.19	5.48	650.0	4
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.16	5.155	690.0	4
Monoamine oxidase CHEMBL2095205	IC50	6.05	6.05	900.0	1
Estrogen receptor CHEMBL2093866	IC50	6.0	6.0	990.0	1
Human immunodeficiency virus type 1 integrase CHEMBL3471	IC50	5.96	5.96	1100.0	1
Neutrophil CHEMBL5314326	IC50	5.96	5.96	1110.0	1
Xanthine dehydrogenase/oxidase CHEMBL3649	IC50	5.76	5.76	1730.0	1
Histone deacetylase 6 CHEMBL1865	IC50	5.72	5.72	1885.0	1
17-beta-hydroxysteroid dehydrogenase type 1 CHEMBL3181	IC50	5.66	5.66	2210.0	1
Amine oxidase [flavin-containing] A CHEMBL1951	IC50	5.6	5.3575	2520.0	4
Maltase-glucoamylase CHEMBL2074	IC50	5.58	5.28	2610.0	2
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	Ki	5.53	5.53	2960.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	5.52	5.52	2991.0	1
Xanthine dehydrogenase/oxidase CHEMBL1929	IC50	5.45	5.45	3530.0	1
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	IC50	5.41	5.41	3890.4	1
Trypanosoma brucei brucei CHEMBL612851	IC50	5.38	5.38	4200.0	1
Cystic fibrosis transmembrane conductance regulator CHEMBL4051	EC50	5.36	5.1233	4400.0	6
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	Ki	5.3	5.3	5000.0	1
Adenosine receptor A1 CHEMBL318	Ki	5.3	5.3	5000.0	2
Solute carrier organic anion transporter family member 2B1 CHEMBL1743124	IC50	5.28	5.28	5248.1	2
Solute carrier family 2, facilitated glucose transporter member 1 CHEMBL2535	Ki	5.16	5.16	7000.0	3
Fatty acid synthase CHEMBL4512	IC50	5.16	5.16	7000.0	1
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	5.16	5.11	6900.0	2
Unchecked CHEMBL612545	EC50	5.16	5.16	7000.0	1
Thromboxane-A synthase CHEMBL1835	IC50	5.11	5.11	7720.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	5.11	5.11	7806.0	1
Transthyretin CHEMBL3194	IC50	5.11	5.11	7800.0	1
ANN-1 CHEMBL614520	IC50	5.1	5.1	8000.0	1
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	IC50	5.04	5.04	9120.1	1
Polyunsaturated fatty acid lipoxygenase ALOX15 CHEMBL4358	IC50	5.04	5.04	9033.0	1
Balb/MK CHEMBL614065	IC50	5.04	5.04	9100.0	1
Proteasome Macropain subunit MB1 CHEMBL4662	IC50	5.03	4.61	9260.0	2
Unchecked CHEMBL612545	Kd	5.03	4.905	9400.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	134.0	nM hr ml	-
AUC	94.91	ng.hr.mL-1	Rattus norvegicus
AUC	94.91	ng.hr.mL-1	Rattus norvegicus
AUC	22970.4	ng.hr.mL-1	Mus musculus
AUC	5134.56	ng.hr.mL-1	Mus musculus
AUC	36752.64	ng.hr.mL-1	Mus musculus
AUC	3945.5	ng.hr.mL-1	Mus musculus
AUC	1459.3	ng.hr.mL-1	Mus musculus
AUC	297.26	ng.hr.mL-1	Mus musculus
AUC	3118.57	ng.hr.mL-1	Mus musculus
AUC	2702.4	ng.hr.mL-1	Mus musculus
AUC	1351.2	ng.hr.mL-1	Mus musculus
AUC	243.22	ng.hr.mL-1	Mus musculus
AUC	4434.64	ng.hr.mL-1	Mus musculus
AUC	1634.95	ng.hr.mL-1	Mus musculus
AUC	191.87	ng.hr.mL-1	Mus musculus
AUC	97.29	ng.hr.mL-1	Mus musculus
Cmax	30.82	nM	Rattus norvegicus
Cmax	30.82	nM	Rattus norvegicus
Cmax	200.0	nM	Mus musculus
Cmax	1100.0	nM	Mus musculus
Cmax	4420.0	nM	Mus musculus
Cmax	2680.0	nM	Mus musculus
Cmax	3350.0	nM	Mus musculus
Cmax	650.0	nM	Mus musculus
Cmax	230.0	nM	Mus musculus
Cmax	100.0	nM	Mus musculus
Cmax	17000.0	nM	Mus musculus
Cmax	35000.0	nM	Mus musculus
Ka	0.31	/mM	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Estrogen receptor beta	Ki	=	0.594	nM	9.23	DRUGMATRIX: Estrogen ERbeta radioligand binding (ligand: [3H] Estradiol)	-
Estrogen receptor beta	IC50	=	1.3	nM	8.89	Displacement of [3H]17beta-estradiol from recombinant human ERbeta expressed in ...	16219463
Estrogen receptor beta	EC50	=	1.7	nM	8.77	Agonist activity in transcriptional activation assay in SH-SY5Y neuroblastoma ce...	11906280
Estrogen receptor beta	EC50	=	2.4	nM	8.62	Estrogenic activity at ERbeta (unknown origin) expressed in human MDA-MB-231/bet...	29641206
Estrogen receptor beta	IC50	=	2.88	nM	8.54	DRUGMATRIX: Estrogen ERbeta radioligand binding (ligand: [3H] Estradiol)	-
Estrogen receptor beta	IC50	=	4.0	nM	8.4	Binding affinity against human estrogen receptor beta (ER beta) in competitive b...	15006374
Estrogen receptor beta	EC50	=	4.1	nM	8.39	Activation of estrogen response element in HeLa cells stably transfected with hu...	11906280
Aldehyde oxidase	IC50	=	5.0	nM	8.3	Inhibition of human liver AOX using phthalazine as substrate incubated for 2.5 m...	31877540
Estrogen receptor beta	EC50	=	6.0	nM	8.22	Transcriptional potency (EC50) at Human estrogen receptor Beta	11708925
Estrogen receptor beta	IC50	=	6.8	nM	8.17	Displacement of [3H]17beta-estradiol from recombinant human ERbeta	17574424
Estrogen receptor	IC50	=	9.7	nM	8.01	Inhibition of human LBD of of ERalpha	17049855
Estrogen receptor beta	IC50	=	9.7	nM	8.01	Inhibition of human ERbeta by radioligand binding assay	17188490
Estrogen receptor beta	IC50	=	9.7	nM	8.01	Inhibition of [3H]17-beta-estradiol binding to human estrogen receptor beta expr...	15943471
Estrogen receptor beta	IC50	=	10.0	nM	8.0	Binding affinity towards human estrogen receptor beta (ERbeta)	12824043
Estrogen receptor beta	IC50	=	10.0	nM	8.0	Binding affinity for human Estrogen receptor beta	15341953
Estrogen receptor beta	IC50	=	10.0	nM	8.0	Inhibitory concentration against human ER beta expressed in Escherichia coli was...	15456246
Estrogen receptor beta	IC50	=	10.0	nM	8.0	Binding affinity for human Estrogen receptor beta	16098741
Steroid hormone receptor ERR1	IC50	=	10.0	nM	8.0	Inhibition of human ERalpha	17482813
Estrogen receptor beta	IC50	=	18.0	nM	7.75	Displacement of [3H]estradiol from human recombinant ERbeta	12502307
Estrogen receptor beta	EC50	=	19.95	nM	7.7	Agonist activity at human ER-beta transfected in HEK293 cells after 48 hrs by lu...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	432
18163589	10.1021/np070230s	L1210	33
22736306	10.1124/dmd.111.043901	Mus musculus	30
17158054	10.1016/j.bmc.2006.09.024	HT-1080	21
19969457	10.1016/j.bmcl.2009.11.103	Achaea janata	20
33646787	10.1021/acs.jnatprod.0c01387	Unchecked	17
22736306	10.1124/dmd.111.043901	ADMET	17
19660945	10.1016/j.bmcl.2009.07.089	DU-145	11
26241875	10.1016/j.ejmech.2015.07.042	Rattus norvegicus	11
29456113	10.1016/j.bmc.2018.01.009	LNCaP	9
24456004	10.1021/np4007712	A-431	8
34028270	10.1021/acs.jmedchem.1c00343	Cystic fibrosis transmembrane conductance regulator	8
36731248	10.1016/j.bmc.2023.117187	Staphylococcus aureus	7
22197393	10.1016/j.bmcl.2011.12.023	Jurkat	6
17411092	10.1021/np060609z	DNA topoisomerase 1	6
22050191	10.1021/jm2007968	Nucleic Acid	6
11708925	10.1021/jm010254a	Estrogen receptor	6
17411092	10.1021/np060609z	DNA topoisomerase 2-alpha	6
25127153	10.1016/j.ejmech.2014.08.032	RAW264.7	6
-	10.1016/S0960-894X(97)00215-1	Cavia porcellus	6

Data from ChEMBL 36 via Core Engine