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Compound Detail

CHEMBL262597

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COc1ccc(C(=O)/C=C/c2ccc(OC)c(OC)c2)c(O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL262597
Phase Preclinical
Structure Type MOL
InChI Key SKTAHPCCLORHHM-XBXARRHUSA-N
4
Targets
5
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

314.3
MW (Da)
3.31
ALogP
5
HBA
1
HBD
65.0
PSA (Ų)
0.65
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H18O5
MW 314.34
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness 0.32

Activity Summary

IC50 5 meas. best 5.97

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 5.97 5.815 1060.0 2
Plasmodium falciparum
CHEMBL364
 IC50 5.5 5.5 3180.0 1
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 IC50 4.86 4.86 13800.0 1
K562
CHEMBL385
 IC50 4.8 4.8 16000.0 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 = 1060.0 nM 5.97 Inhibition of human BCRP expressed in MDCK2 cells assessed as Hoechst 33342 accu... 22112540
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 2170.0 nM 5.66 Inhibition of BCRP in human MCF7/MX cells assessed as Hoechst 33342 accumulation... 22112540
Plasmodium falciparum IC50 = 3180.0 nM 5.5 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum NF54... 33744688
Receptor-type tyrosine-protein kinase FLT3 IC50 = 13800.0 nM 4.86 Inhibition of FLT3 (unknown origin) in presence of ATP 32975953
K562 IC50 = 16000.0 nM 4.8 Antiproliferative activity against human K562 cells after 5 days by MTT assay 19837593

Literature References

PubMed DOI Target Context # Activities
28256373 10.1016/j.bmcl.2017.02.038 RAW264.7 9
32975953 10.1021/acs.jnatprod.0c00699 Receptor-type tyrosine-protein kinase FLT3 3
32975953 10.1021/acs.jnatprod.0c00699 MV4-11 3
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 Cytochrome P450 2D6 2
28064141 10.1016/j.ejmech.2016.12.017 786-0 2
28064141 10.1016/j.ejmech.2016.12.017 WI-38 2
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 A549 2
25027933 10.1016/j.bmcl.2014.06.061 RAW264.7 2
22727643 10.1016/j.bmcl.2012.05.112 Staphylococcus aureus 2
22449016 10.1021/jm2016528 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
32975953 10.1021/acs.jnatprod.0c00699 K562 2
22112540 10.1016/j.bmc.2011.10.074 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
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

Data from ChEMBL 36 via Core Engine