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Compound Detail

CHEMBL252642

LIQUIRTIGENIN
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O=C1C[C@@H](c2ccc(O)cc2)Oc2cc(O)ccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL252642
Name LIQUIRTIGENIN
Phase Preclinical
Structure Type MOL
InChI Key FURUXTVZLHCCNA-AWEZNQCLSA-N
15
Targets
21
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

256.3
MW (Da)
2.80
ALogP
4
HBA
2
HBD
66.8
PSA (Ų)
0.82
QED
0
Ro5 Violations
1
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 1.37

Activity Summary

IC50 19 meas. best 6.47
EC50 1 meas. best 7.44
Ki 1 meas. best 4.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor beta
CHEMBL242
 EC50 7.44 7.44 36.5 1
Aromatase
CHEMBL1978
 IC50 6.47 6.075 340.0 2
Tubulin
CHEMBL2095182
 IC50 6.47 6.47 340.0 1
Neuraminidase
CHEMBL6135
 IC50 5.68 5.38 2070.0 2
No relevant target
CHEMBL2362975
 IC50 5.05 5.05 8960.0 1
Acetylcholinesterase
CHEMBL4078
 IC50 5.04 5.04 9100.0 1
Tyrosine-protein kinase Yes
CHEMBL2073
 IC50 4.95 4.95 11300.0 1
Xanthine dehydrogenase/oxidase
CHEMBL3649
 IC50 4.95 4.95 11300.0 1
Cholinesterase
CHEMBL5763
 IC50 4.85 4.85 14040.0 1
Unchecked
CHEMBL612545
 IC50 4.83 4.6267 14700.0 3
RAW264.7
CHEMBL612557
 IC50 4.79 4.79 16340.0 1
Unchecked
CHEMBL612545
 Ki 4.48 4.48 33100.0 1
HCT-116
CHEMBL394
 IC50 4.43 4.43 37200.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.25 4.13 56600.0 2
Peritoneal macrophage
CHEMBL5314330
 IC50 4.07 4.07 85000.0 1
SGC-7901
CHEMBL614909
 IC50 4.03 4.03 92400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor beta EC50 = 36.5 nM 7.44 Agonist activity at ER-beta (unknown origin) 35964426
Aromatase IC50 = 340.0 nM 6.47 Inhibition of human aromatase by fluorometric assay 18778944
Tubulin IC50 = 340.0 nM 6.47 Inhibition of microtubule polymerization in human K562 cells measured for 60 min... 38295689
Aromatase IC50 = 2100.0 nM 5.68 Inhibition of human aromatase in placental microsomes 18042388
Neuraminidase IC50 = 2070.0 nM 5.68 Inhibition of Influenza A virus (A/Puerto Rico/8/1934(H1N1)) neuraminidase by ch... 24313801
Neuraminidase IC50 = 8330.0 nM 5.08 Inhibition of oseltamivir-resistant Influenza A virus H1N1 B/55/08 neuraminidase... 24313801
No relevant target IC50 = 8960.0 nM 5.05 Antioxidant activity assessed as ABTS radical scavenging activity 34371131
Acetylcholinesterase IC50 = 9100.0 nM 5.04 Inhibition of electric eel AChE using acetylthiocholine iodide as substrate incu... 34371131
Xanthine dehydrogenase/oxidase IC50 = 11300.0 nM 4.95 Inhibition of cow milk xanthine oxidase 3379415
Tyrosine-protein kinase Yes IC50 = 11300.0 nM 4.95 Inhibition of YES (unknown origin) 30769179
Cholinesterase IC50 = 14040.0 nM 4.85 Inhibition of equine serum BuChE using butyrylthiocholine chloride as substrate ... 34371131
Unchecked IC50 = 14700.0 nM 4.83 Inhibition of melanin synthesis in NHEM after 24 hrs by liquid scintillation 19102656
RAW264.7 IC50 = 16340.0 nM 4.79 Anti-inflammatory activity against mouse RAW264.7 cells assessed as reduction in... 37683361
Unchecked IC50 = 19080.0 nM 4.72 Inhibition of nitric oxide synthase (unknown origin) 37683361
Unchecked Ki = 33100.0 nM 4.48 Inhibition of Spanish flu (A/Bervig_Mission/1/18) neuraminidase by noncompetitiv... 20064716
HCT-116 IC50 = 37200.0 nM 4.43 Cytotoxicity against human HCT116 cells after 72 hrs by MTT assay 20494492
Unchecked IC50 = 46800.0 nM 4.33 Inhibition of Spanish flu (A/Bervig_Mission/1/18) neuraminidase 20064716
NON-PROTEIN TARGET IC50 = 56600.0 nM 4.25 Cytotoxicity against mouse colon 26-L5 cells after 72 hrs by MTT assay 18440233
Peritoneal macrophage IC50 = 85000.0 nM 4.07 Inhibition of LPS-stimulated nitric oxide production in ddy mouse peritoneal mac... 27955927
SGC-7901 IC50 = 92400.0 nM 4.03 Cytotoxicity against human SGC7901 cells after 72 hrs by MTT assay 20494492

Literature References

PubMed DOI Target Context # Activities
37534604 10.1021/acs.jmedchem.3c00815 BNL CL.2 15
37534604 10.1021/acs.jmedchem.3c00815 Unchecked 13
8377021 10.1021/np50097a001 Rattus norvegicus 10
37534604 10.1021/acs.jmedchem.3c00815 Nuclear factor erythroid 2-related factor 2 10
29224994 10.1016/j.bmc.2017.11.046 Mus musculus 9
37534604 10.1021/acs.jmedchem.3c00815 Mus musculus 8
21866899 10.1021/np200174h U-937 7
21866899 10.1021/np200174h Collagenase 4
19928832 10.1021/np900676y T47D 4
24313801 10.1021/np400817j Neuraminidase 4
19928832 10.1021/np900676y MCF7 4
18440233 10.1016/j.bmc.2008.04.016 NON-PROTEIN TARGET 3
21866899 10.1021/np200174h Prevotella intermedia 3
21866899 10.1021/np200174h Matrix metalloproteinase-9 3
20064716 10.1016/j.bmcl.2009.12.106 Unchecked 2
24313801 10.1021/np400817j Influenza A virus 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
3379415 10.1021/np50056a030 Xanthine dehydrogenase/oxidase 2
18042388 10.1016/j.bmc.2007.10.057 Aromatase 2

Data from ChEMBL 36 via Core Engine