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Compound Detail

CHEMBL487402

EUPATORIN
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COc1ccc(-c2cc(=O)c3c(O)c(OC)c(OC)cc3o2)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL487402
Name EUPATORIN
Phase Preclinical
Structure Type MOL
InChI Key KLAOKWJLUQKWIF-UHFFFAOYSA-N
8
Targets
10
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

344.3
MW (Da)
2.90
ALogP
7
HBA
2
HBD
98.4
PSA (Ų)
0.75
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H16O7
MW 344.32
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness 1.23

Activity Summary

Ki 6 meas. best 7.46
IC50 4 meas. best 5.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 1B1
CHEMBL4878
 Ki 7.46 7.46 35.0 2
Aurora kinase B
CHEMBL2185
 Ki 7.4 7.4 39.8 1
Cytochrome P450 1A1
CHEMBL2231
 Ki 6.68 6.68 210.0 1
Vascular endothelial growth factor receptor 2
CHEMBL279
 Ki 6.1 6.1 794.3 1
Aurora kinase A
CHEMBL4722
 Ki 6.0 6.0 1000.0 1
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 IC50 5.96 5.96 1100.0 1
MCF7
CHEMBL387
 IC50 5.16 5.075 7000.0 2
HeLa
CHEMBL399
 IC50 5.09 5.09 8100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 1B1 Ki = 35.0 nM 7.46 Inhibition of CYP1B1 EROD activity assessed as inhibition of deethylation of 7-e... 21482471
Cytochrome P450 1B1 Ki = 35.0 nM 7.46 Inhibition of CYP1B1 (unknown origin) 28458135
Aurora kinase B Ki = 39.81 nM 7.4 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Cytochrome P450 1A1 Ki = 210.0 nM 6.68 Inhibition of CYP1A1 EROD activity assessed as inhibition of deethylation of 7-e... 21482471
Vascular endothelial growth factor receptor 2 Ki = 794.33 nM 6.1 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Aurora kinase A Ki = 1000.0 nM 6.0 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Receptor-type tyrosine-protein kinase FLT3 IC50 = 1100.0 nM 5.96 Inhibition of recombinant His-tagged human FLT3 (564 to 958 residues) expressed ... 33393294
MCF7 IC50 = 7000.0 nM 5.16 Antiproliferative activity in human MCF7 cells after 96 hrs by MTT assay 19601638
HeLa IC50 = 8100.0 nM 5.09 Cytotoxicity against human HeLa cells assessed as reduction in cell viability in... 31784199
MCF7 IC50 = 10300.0 nM 4.99 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability in... 31784199

Literature References

PubMed DOI Target Context # Activities
19601638 10.1021/np900051s MCF7 6
32182064 10.1021/acs.jnatprod.9b01024 Enterococcus faecalis 4
32182064 10.1021/acs.jnatprod.9b01024 Enterococcus faecium 3
32182064 10.1021/acs.jnatprod.9b01024 Staphylococcus aureus 2
32182064 10.1021/acs.jnatprod.9b01024 Staphylococcus epidermidis 2
6512542 10.1021/np50035a034 Bacillus subtilis 2
6512542 10.1021/np50035a034 Escherichia coli 2
21482471 10.1016/j.bmc.2011.03.042 Cytochrome P450 1A1 2
33393294 10.1021/acs.jnatprod.0c00589 Receptor-type tyrosine-protein kinase FLT3 2
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
27679866 10.1021/acs.jnatprod.6b00605 SK-LU-1 1
27679866 10.1021/acs.jnatprod.6b00605 MCF7 1
27679866 10.1021/acs.jnatprod.6b00605 K562 1
27679866 10.1021/acs.jnatprod.6b00605 PC-3 1
27679866 10.1021/acs.jnatprod.6b00605 U-251 1
28458135 10.1016/j.ejmech.2017.04.042 Cytochrome P450 1B1 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
21482471 10.1016/j.bmc.2011.03.042 Cytochrome P450 1B1 1
521819 10.1021/np50005a010 KB 1
8882428 10.1021/np960057s Monocyte 1

Data from ChEMBL 36 via Core Engine