Compound Detail

CHEMBL129795

ISOLIQUIRITIGENIN

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O=C(/C=C/c1ccc(O)cc1)c1ccc(O)cc1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL129795
Name	ISOLIQUIRITIGENIN
Phase	Preclinical
Structure Type	MOL
InChI Key	DXDRHHKMWQZJHT-FPYGCLRLSA-N

Targets

104

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

256.3

MW (Da)

2.70

ALogP

HBA

HBD

77.8

PSA (Å²)

0.58

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	C15H12O4
MW	256.26
Aromatic Rings	2
Heavy Atoms	19
NP-Likeness	0.70

Activity Summary

IC50 98 meas. best 8.1

EC50 3 meas. best 4.94

Ki 3 meas. best 5.55

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Matrilysin CHEMBL4073	IC50	8.1	8.1	8.0	1
72 kDa type IV collagenase CHEMBL333	IC50	8.0	8.0	10.0	1
Matrix metalloproteinase-9 CHEMBL321	IC50	8.0	8.0	10.0	1
Collagenase 3 CHEMBL280	IC50	7.85	7.85	14.0	1
Interstitial collagenase CHEMBL332	IC50	7.8	7.8	16.0	1
Stromelysin-1 CHEMBL283	IC50	7.09	7.09	81.0	1
Estrogen receptor beta CHEMBL242	IC50	6.57	6.57	269.0	1
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	6.5	6.5	320.0	1
17-beta-hydroxysteroid dehydrogenase type 2 CHEMBL2789	IC50	6.44	6.44	360.0	1
Aldo-keto reductase family 1 member B1 CHEMBL2622	IC50	6.4	6.4	400.0	1
NACHT, LRR and PYD domains-containing protein 3 CHEMBL1741208	IC50	5.81	5.405	1540.0	2
Estrogen receptor CHEMBL206	IC50	5.73	5.73	1870.0	1
17-beta-hydroxysteroid dehydrogenase type 1 CHEMBL3181	IC50	5.55	5.55	2830.0	1
Aromatase CHEMBL1978	Ki	5.55	5.55	2800.0	1
PANC-1 CHEMBL614139	IC50	5.48	5.48	3300.0	1
Aromatase CHEMBL1978	IC50	5.42	5.42	3800.0	1
Unchecked CHEMBL612545	IC50	5.32	4.8642	4800.0	12
Proteasome Macropain subunit MB1 CHEMBL4662	IC50	5.31	5.31	4880.0	1
BV-2 CHEMBL614781	IC50	5.28	5.225	5220.0	2
Plasmodium falciparum CHEMBL364	IC50	5.11	4.9263	7800.0	8
Unchecked CHEMBL612545	Ki	5.0	5.0	9900.0	1
MDA-MB-231 CHEMBL400	IC50	4.96	4.78	10860.0	2
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL2492	EC50	4.94	4.94	11600.0	1
Amine oxidase [flavin-containing] A CHEMBL3358	IC50	4.86	4.81	13900.0	2
NAD-dependent protein deacetylase sirtuin-1 CHEMBL4506	IC50	4.76	4.76	17300.0	1
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	IC50	4.76	4.76	17300.0	1
PC-12 CHEMBL612556	IC50	4.75	4.75	17800.0	1
MCF7 CHEMBL387	IC50	4.75	4.75	17670.0	1
Amyloid-beta precursor protein CHEMBL2487	IC50	4.71	4.71	19700.0	1
Leishmania donovani CHEMBL367	IC50	4.68	4.68	20700.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.66	4.2886	21800.0	7
Influenza A virus CHEMBL613740	EC50	4.61	4.61	24700.0	1
MCF-10A CHEMBL614321	IC50	4.6	4.6	25000.0	1
HepG2 CHEMBL395	IC50	4.56	4.56	27710.0	1
K562 CHEMBL385	IC50	4.53	4.53	29270.0	1
J774.1 CHEMBL4296442	IC50	4.53	4.53	29300.0	1
Nuclear factor NF-kappa-B complex CHEMBL2094258	IC50	4.5	4.5	32000.0	1
Trypanosoma brucei brucei CHEMBL612851	IC50	4.48	4.48	32800.0	1
Beta-secretase 1 CHEMBL4822	IC50	4.48	4.385	33000.0	2
C-33-A CHEMBL2366313	IC50	4.48	4.48	32830.0	1
Cyclooxygenase CHEMBL2095157	IC50	4.46	4.46	35000.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL312	IC50	4.46	4.46	35000.0	2
Hepatitis C virus CHEMBL379	EC50	4.44	4.44	36100.0	1
Protein disulfide-isomerase CHEMBL5422	Ki	4.44	4.44	36100.0	1
ADMET CHEMBL612558	IC50	4.44	4.425	36300.0	2
Ca-Ski CHEMBL1075403	IC50	4.41	4.41	39090.0	1
HUVEC CHEMBL613979	IC50	4.38	4.38	41170.0	1
CHO CHEMBL613853	IC50	4.34	4.34	45900.0	1
Amine oxidase [flavin-containing] B CHEMBL2993	IC50	4.33	4.33	47200.0	1
PC-3 CHEMBL390	IC50	4.33	4.165	46400.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
F	11.8	%	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Matrilysin	IC50	=	8.0	nM	8.1	Inhibition of MMP7 in human U2OS cells by peptide microarray-based fluorescence ...	36122348
Matrix metalloproteinase-9	IC50	=	10.0	nM	8.0	Inhibition of MMP9 in human U2OS cells by peptide microarray-based fluorescence ...	36122348
72 kDa type IV collagenase	IC50	=	10.0	nM	8.0	Inhibition of MMP2 in human U2OS cells by peptide microarray-based fluorescence ...	36122348
Collagenase 3	IC50	=	14.0	nM	7.85	Inhibition of MMP13 in human U2OS cells by peptide microarray-based fluorescence...	36122348
Interstitial collagenase	IC50	=	16.0	nM	7.8	Inhibition of MMP1 in human U2OS cells by peptide microarray-based fluorescence ...	36122348
Stromelysin-1	IC50	=	81.0	nM	7.09	Inhibition of MMP3 in human U2OS cells by peptide microarray-based fluorescence ...	36122348
Estrogen receptor beta	IC50	=	269.0	nM	6.57	Displacement of estradiol from human ERbetaa expressed in yeast cells	28319389
Aldo-keto reductase family 1 member B1	IC50	=	320.0	nM	6.5	Inhibition of human recombinant aldose reductase using D-glyceraldehyde as subst...	22261024
17-beta-hydroxysteroid dehydrogenase type 2	IC50	=	360.0	nM	6.44	Inhibition of human 17beta-HSD2 expressed in HEK293 cell lysates incubated for 1...	28319389
Aldo-keto reductase family 1 member B1	IC50	=	400.0	nM	6.4	Inhibition of Rattus norvegicus (rat) lens aldose reductase	-
NACHT, LRR and PYD domains-containing protein 3	IC50	=	1540.0	nM	5.81	Inhibition of NLRP3 inflammasome in human THP1 cells assessed as reduction in MS...	29472126
Estrogen receptor	IC50	=	1870.0	nM	5.73	Displacement of estradiol from human ERalpha expressed in yeast cells	28319389
Aromatase	Ki	=	2800.0	nM	5.55	Inhibition of aromatase (unknown origin) assessed as inhbition constant	37690265
17-beta-hydroxysteroid dehydrogenase type 1	IC50	=	2830.0	nM	5.55	Inhibition of human 17beta-HSD1 expressed in HEK293 cell lysates incubated for 1...	28319389
PANC-1	IC50	=	3300.0	nM	5.48	Cytotoxicity against human PANC1 cells after 72 hrs by WST8 assay	28495081
Aromatase	IC50	=	3800.0	nM	5.42	Inhibition of aromatase (unknown origin)	28319389
Unchecked	IC50	=	4800.0	nM	5.32	Inhibition of cobalt chloride-induced HIF-1 activation expressed in mouse NIH3T3...	21112783
Proteasome Macropain subunit MB1	IC50	=	4880.0	nM	5.31	Inhibition of chymotrypsin-like activity of purified human erythrocyte 20S prote...	30776692
BV-2	IC50	=	5220.0	nM	5.28	Anti-inflammatory activity in mouse BV-2 cells assessed as reduction in LPS-indu...	37683361
Unchecked	IC50	=	5600.0	nM	5.25	Inhibition of alpha-Glucosidase (unknown origin) using pNPG as substrate incubat...	32196343

Literature References

PubMed	DOI	Target Context	# Activities
22743086	10.1016/j.bmc.2012.05.062	Influenza A virus	20
28571822	10.1016/j.bmcl.2017.05.054	Hep 3B2	17
22169259	10.1016/j.bmcl.2011.11.059	Staphylococcus aureus	15
21866899	10.1021/np200174h	U-937	14
28571822	10.1016/j.bmcl.2017.05.054	NIH3T3	10
36122348	10.1021/acs.jnatprod.2c00626	ADMET	10
28252963	10.1021/acs.jnatprod.6b00600	No relevant target	9
28655421	10.1016/j.bmcl.2017.01.053	Mus musculus	9
29224994	10.1016/j.bmc.2017.11.046	Mus musculus	7
22743086	10.1016/j.bmc.2012.05.062	MDCK	7
37659218	10.1016/j.bmc.2023.117454	Unchecked	7
16562858	10.1021/np050362q	Unchecked	7
21866899	10.1021/np200174h	Prevotella intermedia	6
36122348	10.1021/acs.jnatprod.2c00626	U2OS	6
19734910	10.1038/nchembio.215	Plasmodium falciparum	6
21866899	10.1021/np200174h	Porphyromonas gingivalis	5
22743086	10.1016/j.bmc.2012.05.062	Protein kinase C (PKC)	5
21123068	10.1016/j.bmcl.2010.11.016	Neuraminidase	5
19928832	10.1021/np900676y	T47D	4
19928832	10.1021/np900676y	MCF7	4

Data from ChEMBL 36 via Core Engine