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Compound Detail

CHEMBL226508

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COc1ccc(-c2cc(=O)c3c(O)c(OC)c(OC)cc3o2)cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL226508
Phase Preclinical
Structure Type MOL
InChI Key QEWSAPKRFOFQIU-UHFFFAOYSA-N
6
Targets
8
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

358.4
MW (Da)
3.20
ALogP
7
HBA
1
HBD
87.4
PSA (Ų)
0.75
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H18O7
MW 358.35
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness 0.97

Activity Summary

IC50 5 meas. best 6.05
Ki 3 meas. best 6.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 1A2
CHEMBL3356
 Ki 6.11 6.11 780.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 6.05 6.05 900.0 1
Cytochrome P450 1A1
CHEMBL2231
 IC50 5.86 5.86 1380.0 1
Cytochrome P450 1A1
CHEMBL2231
 Ki 5.85 5.85 1420.0 1
Cytochrome P450 1B1
CHEMBL4878
 IC50 5.6 5.6 2500.0 1
Delta-type opioid receptor
CHEMBL236
 Ki 5.51 5.51 3100.0 1
HeLa
CHEMBL399
 IC50 5.09 5.09 8100.0 1
MCF7
CHEMBL387
 IC50 4.99 4.99 10300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 1A2 Ki = 780.0 nM 6.11 Inhibition of human recombinant CYP1A2 expressed in HEK293 cells using 3-cyano-7... 30108931
Cytochrome P450 1A2 IC50 = 900.0 nM 6.05 Inhibition of human recombinant CYP1A2 expressed in HEK293 cells using 3-cyano-7... 30108931
Cytochrome P450 1A1 IC50 = 1380.0 nM 5.86 Inhibition of human recombinant CYP1A1 expressed in HEK293 cells using 7-ethoxyr... 30108931
Cytochrome P450 1A1 Ki = 1420.0 nM 5.85 Inhibition of human recombinant CYP1A1 expressed in HEK293 cells using 7-ethoxyr... 30108931
Cytochrome P450 1B1 IC50 = 2500.0 nM 5.6 Inhibition of human recombinant CYP1B1 expressed in HEK293 cells using 7-ethoxyr... 30108931
Delta-type opioid receptor Ki = 3100.0 nM 5.51 Displacement of [3H]DPDPE from delta opioid receptor (unknown origin) transfecte... 26035635
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
18656366 10.1016/j.bmc.2008.07.018 RBL-2H3 4
30108931 10.1039/C7MD00388A Cytochrome P450 1A1 4
30108931 10.1039/C7MD00388A Cytochrome P450 1A2 3
26035635 10.1021/acs.jnatprod.5b00218 Delta-type opioid receptor 3
30108931 10.1039/C7MD00388A Cytochrome P450 1B1 2
6512542 10.1021/np50035a034 Pseudomonas aeruginosa 2
6512542 10.1021/np50035a034 Escherichia coli 2
30108931 10.1039/C7MD00388A Cytochrome P450 2D6 2
30108931 10.1039/C7MD00388A Cytochrome P450 3A4 2
30108931 10.1039/C7MD00388A Cytochrome P450 2C19 2
17391969 10.1016/j.bmc.2007.03.021 HL-60 2
30108931 10.1039/C7MD00388A Cytochrome P450 2C9 2
18656366 10.1016/j.bmc.2008.07.018 Mitogen-activated protein kinase 8 1
26035635 10.1021/acs.jnatprod.5b00218 Cannabinoid receptor 2 1
18656366 10.1016/j.bmc.2008.07.018 Radical scavenging activity 1
18656366 10.1016/j.bmc.2008.07.018 Mitogen-activated protein kinase 1 and 3 (ERK2 and ERK1) 1
18656366 10.1016/j.bmc.2008.07.018 Tyrosine-protein kinase SYK 1
18656366 10.1016/j.bmc.2008.07.018 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1 1
37683361 10.1016/j.ejmech.2023.115791 Unchecked 1
521819 10.1021/np50005a010 KB 1

Data from ChEMBL 36 via Core Engine