Compound Detail

CHEMBL399121

HESPERETIN

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COc1ccc([C@@H]2CC(=O)c3c(O)cc(O)cc3O2)cc1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL399121
Name	HESPERETIN
Phase	Preclinical
Structure Type	MOL
InChI Key	AIONOLUJZLIMTK-AWEZNQCLSA-N

Known Names

(-)-hesperetin Eriodictyol 4'-monomethyl ether FEMA NO. 4313 Hesperetin Hesperitin NSC-57654

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

302.3

MW (Da)

2.52

ALogP

HBA

HBD

96.2

PSA (Å²)

0.79

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Stem

-retin

Extended Properties

Molecular Formula	C16H14O6
MW	302.28
Aromatic Rings	2
Heavy Atoms	22
NP-Likeness	1.71

Activity Summary

IC50 19 meas. best 6.55

Ki 3 meas. best 8.48

Kd 1 meas. best 4.61

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Carbonic anhydrase 7 CHEMBL2326	Ki	8.48	8.48	3.3	1
Carbonic anhydrase 4 CHEMBL3729	Ki	6.99	6.99	102.1	1
Dipeptidyl peptidase 4 CHEMBL284	IC50	6.55	6.55	280.0	1
Carbonic anhydrase 12 CHEMBL3242	Ki	6.34	6.34	454.1	1
Cytochrome P450 1B1 CHEMBL4878	IC50	6.29	6.29	511.0	1
Xanthine dehydrogenase/oxidase CHEMBL1929	IC50	6.08	6.08	840.0	1
Histone deacetylase 6 CHEMBL1865	IC50	6.0	6.0	998.0	1
Monocyte CHEMBL614076	IC50	5.68	5.68	2100.0	1
Cytochrome P450 1A1 CHEMBL2231	IC50	5.55	5.55	2786.0	1
Replicase polyprotein 1ab CHEMBL5118	IC50	5.08	4.65	8300.0	2
Unchecked CHEMBL612545	IC50	5.08	5.08	8300.0	1
Replicase polyprotein 1ab CHEMBL5118	Kd	4.61	4.61	24500.0	1
Glycogen synthase kinase-3 beta CHEMBL262	IC50	4.57	4.57	26900.0	1
RAW264.7 CHEMBL612557	IC50	4.51	4.41	31200.0	2
Cytochrome P450 1A2 CHEMBL3356	IC50	4.46	4.46	34647.0	1
PC-3 CHEMBL390	IC50	4.4	4.225	40000.0	2
Caco-2 CHEMBL614058	IC50	4.18	4.18	66670.0	1
Lysine-specific histone demethylase 1A CHEMBL6136	IC50	4.1	4.1	78760.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Ka	0.66	10'5/M	Homo sapiens
Ke	10000.0	nM	Homo sapiens
Ke	10000.0	nM	Homo sapiens
Ke	10000.0	nM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Carbonic anhydrase 7	Ki	=	3.3	nM	8.48	Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins at...	26498393
Carbonic anhydrase 4	Ki	=	102.1	nM	6.99	Inhibition of human recombinant carbonic anhydrase 4 preincubated for 15 mins at...	26498393
Dipeptidyl peptidase 4	IC50	=	280.0	nM	6.55	Inhibition of DPP4 (unknown origin) using Gly-Pro-AMC as substrate preincubated ...	29609120
Carbonic anhydrase 12	Ki	=	454.1	nM	6.34	Inhibition of human recombinant carbonic anhydrase 12 preincubated for 15 mins a...	26498393
Cytochrome P450 1B1	IC50	=	511.0	nM	6.29	Inhibition of human CYP1B1 by EROD assay	20696580
Xanthine dehydrogenase/oxidase	IC50	=	840.0	nM	6.08	Inhibition of XO (unknown origin) using xanthine as substrate assessed as reduct...	37908076
Histone deacetylase 6	IC50	=	998.0	nM	6.0	Determination of IC50 values for inhibition of enzymatic assay of human HDAC6 wi...	-
Monocyte	IC50	=	2100.0	nM	5.68	Inhibition of procoagulant activity in monocyte from human blood assessed as cou...	8882428
Cytochrome P450 1A1	IC50	=	2786.0	nM	5.55	Inhibition of human CYP1A1 by EROD assay	20696580
Replicase polyprotein 1ab	IC50	=	8300.0	nM	5.08	Inhibition of SARS coronavirus 3C-like protease cis-cleavage activity transfecte...	23647823
Unchecked	IC50	=	8300.0	nM	5.08	Inhibition of SARS-CoV 3C-like protease expressed in African green monkey Vero c...	32845145
Replicase polyprotein 1ab	Kd	=	24500.0	nM	4.61	Binding affinity to SARS coronavirus 3C-like protease by SPR analysis	23647823
Glycogen synthase kinase-3 beta	IC50	=	26900.0	nM	4.57	Inhibition of Homo sapiens (human) recombinant GSK3beta after 30 min by Kinase-G...	-
RAW264.7	IC50	=	31200.0	nM	4.51	Inhibition of LPS induced NO production in mouse RAW264.7 cells measured after 2...	33667099
Cytochrome P450 1A2	IC50	=	34647.0	nM	4.46	Inhibition of human CYP1A2 by EROD assay	20696580
PC-3	IC50	=	40000.0	nM	4.4	Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay	31398616
RAW264.7	IC50	=	48590.0	nM	4.31	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-...	33493826
Replicase polyprotein 1ab	IC50	=	60000.0	nM	4.22	Inhibition of recombinant SARS coronavirus 3C-like protease trans-cleavage activ...	23647823
Caco-2	IC50	=	66670.0	nM	4.18	Cytotoxicity in human Caco2 cells after 72 hrs by MTT assay	28793973
Lysine-specific histone demethylase 1A	IC50	=	78760.0	nM	4.1	Inhibition of LSD1 (unknown origin) by fluorescence assay	30552007

Literature References

PubMed	DOI	Target Context	# Activities
26517554	10.1021/acs.jnatprod.5b00075	ADMET	10
33493826	10.1016/j.ejmech.2021.113162	RAW264.7	6
23153811	10.1016/j.ejmech.2012.10.028	TGF-beta receptor type-2	5
18249545	10.1016/j.bmc.2008.01.028	No relevant target	5
18249545	10.1016/j.bmc.2008.01.028	Caco-2	5
22429094	10.1021/np200696r	Oxysterols receptor LXR-alpha	4
27840137	10.1016/j.bmc.2016.11.006	HCT-116	4
21824690	10.1016/j.ejmech.2011.07.031	HepG2	4
33530021	10.1016/j.bmc.2021.116043	Cytochrome c	4
-	10.6019/CHEMBL4808148	Histone deacetylase 6	4
12873489	10.1016/s0960-894x(03)00574-2	Mus musculus	4
26848111	10.1016/j.bmcl.2016.01.058	RAW264.7	3
19944611	10.1016/j.bmc.2009.11.015	No relevant target	3
23153811	10.1016/j.ejmech.2012.10.028	HeLa	3
17166721	10.1016/j.bmc.2006.11.037	NON-PROTEIN TARGET	3
23623675	10.1016/j.bmc.2013.02.055	Serum paraoxonase/arylesterase 1	3
26517554	10.1021/acs.jnatprod.5b00075	Unchecked	3
23647823	10.1016/j.bmc.2013.04.026	Replicase polyprotein 1ab	3
23153811	10.1016/j.ejmech.2012.10.028	Unchecked	3
22429094	10.1021/np200696r	Peroxisome proliferator-activated receptor gamma	2

Data from ChEMBL 36 via Core Engine