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Compound Detail

CHEMBL260597

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COc1cccc(/C=C/C(=O)c2ccc(OC)cc2O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL260597
Phase Preclinical
Structure Type MOL
InChI Key IXNMOBIPLWIWDF-RMKNXTFCSA-N
3
Targets
5
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

284.3
MW (Da)
3.31
ALogP
4
HBA
1
HBD
55.8
PSA (Ų)
0.68
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 C17H16O4
MW 284.31
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 0.21

Activity Summary

IC50 4 meas. best 5.83
EC50 1 meas. best 5.47

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 5.83 5.665 1470.0 2
RAW264.7
CHEMBL612557
 IC50 5.5 5.015 3200.0 2
Trypanosoma brucei brucei
CHEMBL612851
 EC50 5.47 5.47 3400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 1470.0 nM 5.83 Inhibition of human BCRP expressed in MDCK2 cells assessed as Hoechst 33342 accu... 22112540
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 3150.0 nM 5.5 Inhibition of BCRP in human MCF7/MX cells assessed as Hoechst 33342 accumulation... 22112540
RAW264.7 IC50 = 3200.0 nM 5.5 Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells measur... 32208222
Trypanosoma brucei brucei EC50 = 3400.0 nM 5.47 Anti-parasitic activity against bloodstream form of Trypanosoma brucei brucei Li... 28064141
RAW264.7 IC50 = 29700.0 nM 4.53 Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viabilit... 32208222

Literature References

PubMed DOI Target Context # Activities
32208222 10.1016/j.ejmech.2020.112216 RAW264.7 3
28064141 10.1016/j.ejmech.2016.12.017 Trypanosoma cruzi 2
28064141 10.1016/j.ejmech.2016.12.017 Cytochrome P450 3A4 2
28064141 10.1016/j.ejmech.2016.12.017 Cytochrome P450 2D6 2
28064141 10.1016/j.ejmech.2016.12.017 Cytochrome P450 2C19 2
28064141 10.1016/j.ejmech.2016.12.017 Cytochrome P450 2C9 2
28064141 10.1016/j.ejmech.2016.12.017 Cytochrome P450 1A2 2
28064141 10.1016/j.ejmech.2016.12.017 Voltage-gated inwardly rectifying potassium channel KCNH2 2
28064141 10.1016/j.ejmech.2016.12.017 786-0 2
28064141 10.1016/j.ejmech.2016.12.017 A549 2
28064141 10.1016/j.ejmech.2016.12.017 WI-38 2
28064141 10.1016/j.ejmech.2016.12.017 Trypanosoma brucei brucei 2
22112540 10.1016/j.bmc.2011.10.074 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
18293907 10.1021/jm0708331 K562 1
28064141 10.1016/j.ejmech.2016.12.017 Leishmania infantum 1
28064141 10.1016/j.ejmech.2016.12.017 Aurora kinase B 1
28064141 10.1016/j.ejmech.2016.12.017 Unchecked 1
28064141 10.1016/j.ejmech.2016.12.017 THP-1 1
22112540 10.1016/j.bmc.2011.10.074 Multidrug resistance-associated protein 1 1
22112540 10.1016/j.bmc.2011.10.074 ATP-dependent translocase ABCB1 1

Data from ChEMBL 36 via Core Engine