Compound Detail

CHEMBL312750

EUPATILIN

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COc1ccc(-c2cc(=O)c3c(O)c(OC)c(O)cc3o2)cc1OC

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL312750
Name	EUPATILIN
Phase	Preclinical
Structure Type	MOL
InChI Key	DRRWBCNQOKKKOL-UHFFFAOYSA-N

Eupatilin NSC-122413

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

344.3

MW (Da)

2.90

ALogP

HBA

HBD

98.4

PSA (Å²)

0.75

QED

Ro5 Violations

Rot. Bonds

Molecule Type	Small molecule
Chirality	Achiral

Natural Product

IC50 10 meas. best 5.88

Ki 2 meas. best 4.92

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histone deacetylase 6 CHEMBL1865	IC50	5.88	5.88	1316.0	1
T-cell CHEMBL614309	IC50	4.93	4.93	11700.0	1
Delta-type opioid receptor CHEMBL3222	Ki	4.92	4.92	12000.0	1
Unchecked CHEMBL612545	IC50	4.68	4.4267	20900.0	3
Mu-type opioid receptor CHEMBL2858	Ki	4.55	4.55	28000.0	1
AGS CHEMBL613860	IC50	4.3	4.3	50000.0	1
MKN-1 CHEMBL614352	IC50	4.3	4.3	50000.0	1
SNU-638 CHEMBL614935	IC50	4.3	4.3	50000.0	1
HepG2 CHEMBL395	IC50	4.28	4.28	52650.0	1
MCF7 CHEMBL387	IC50	4.04	4.04	90070.0	1

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histone deacetylase 6	IC50	=	1316.0	nM	5.88	Determination of IC50 values for inhibition of enzymatic assay of human HDAC6 wi...	-
T-cell	IC50	=	11700.0	nM	4.93	Immunosuppressant activity in human T lymphocytes assessed as inhibition of anti...	31181920
Delta-type opioid receptor	Ki	=	12000.0	nM	4.92	Displacement of [3H]DPDPE from delta opioid receptor in CD1 mouse whole brain mi...	25562563
Unchecked	IC50	=	20900.0	nM	4.68	Inhibition of AKT activity in human MM121224 cells harboring BRAF V600E/NRAS Q61...	35640148
Mu-type opioid receptor	Ki	=	28000.0	nM	4.55	Displacement of [3H]DAMGO from mu opioid receptor in CD1 mouse whole brain minus...	25562563
SNU-638	IC50	=	50000.0	nM	4.3	Antiproliferative activity against human SNU638 cells assessed as reduction in c...	31784199
Unchecked	IC50	=	50000.0	nM	4.3	Antiproliferative activity against human SNU601 cells assessed as reduction in c...	31784199
Unchecked	IC50	=	50000.0	nM	4.3	Antiproliferative activity against human SNU484 cells assessed as reduction in c...	31784199
AGS	IC50	=	50000.0	nM	4.3	Antiproliferative activity against human AGS cells assessed as reduction in cell...	31784199
MKN-1	IC50	=	50000.0	nM	4.3	Antiproliferative activity against human MKN1 cells assessed as reduction in cel...	31784199
HepG2	IC50	=	52650.0	nM	4.28	Cytotoxicity against human HepG2 cells assessed as reduction in cell growth incu...	27400887
MCF7	IC50	=	90070.0	nM	4.04	Cytotoxicity against human MCF7 cells assessed as reduction in cell growth incub...	27400887

PubMed	DOI	Target Context	# Activities
30177376	10.1016/j.bmcl.2018.08.034	HUVEC	8
-	10.6019/CHEMBL4808148	Histone deacetylase 6	4
30177376	10.1016/j.bmcl.2018.08.034	SNU-182	3
30177376	10.1016/j.bmcl.2018.08.034	HepG2	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
31784199	10.1016/j.bmc.2019.115180	Unchecked	2
35640148	10.1021/acs.jnatprod.2c00146	Unchecked	2
30177376	10.1016/j.bmcl.2018.08.034	RAC-alpha serine/threonine-protein kinase	2
9632366	10.1021/jm970842h	Tubulin	2
37683361	10.1016/j.ejmech.2023.115791	Rattus norvegicus	1
26035635	10.1021/acs.jnatprod.5b00218	Delta-type opioid receptor	1
9632366	10.1021/jm970842h	Panel NCI-60 (60 carcinoma cell lines)	1
26035635	10.1021/acs.jnatprod.5b00218	Mu-type opioid receptor	1
26035635	10.1021/acs.jnatprod.5b00218	Cannabinoid receptor 1	1
26035635	10.1021/acs.jnatprod.5b00218	Cannabinoid receptor 2	1
-	10.21203/rs.3.rs-23951/v1	SARS-CoV-2	1
25562563	10.1021/np500671v	Unchecked	1
31784199	10.1016/j.bmc.2019.115180	SNU-638	1
25562563	10.1021/np500671v	Mu-type opioid receptor	1
31784199	10.1016/j.bmc.2019.115180	AGS	1

Data from ChEMBL 36 via Core Engine