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Compound Detail

CHEMBL229907

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COc1ccc(/C=C/C(=O)c2ccc(OC)cc2O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL229907
Phase Preclinical
Structure Type MOL
InChI Key OAAPAFSEMHJNTF-BJMVGYQFSA-N
5
Targets
6
Activities
1
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 0.32

Activity Summary

IC50 6 meas. best 5.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 5.66 5.52 2200.0 2
Amyloid-beta precursor protein
CHEMBL2487
 IC50 5.08 5.08 8400.0 1
Unchecked
CHEMBL612545
 IC50 4.8 4.8 15900.0 1
SK-MEL-1
CHEMBL614916
 IC50 4.38 4.38 41730.0 1
MCF7
CHEMBL387
 IC50 4.34 4.34 45390.0 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 = 2200.0 nM 5.66 Inhibition of human BCRP expressed in MDCK2 cells assessed as Hoechst 33342 accu... 22112540
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 4200.0 nM 5.38 Inhibition of BCRP in human MCF7/MX cells assessed as Hoechst 33342 accumulation... 22112540
Amyloid-beta precursor protein IC50 = 8400.0 nM 5.08 Inhibition of amyloid beta (1-42) self-mediated aggregation (unknown origin) aft... 23786711
Unchecked IC50 = 15900.0 nM 4.8 Inhibition of potato 5-LOX using linoleic acid as substrate assessed as hydroper... 23786711
SK-MEL-1 IC50 = 41730.0 nM 4.38 Cytotoxicity against human SK-MEL-1 cells by MTT assay 19447618
MCF7 IC50 = 45390.0 nM 4.34 Cytotoxicity against human MCF7 cells by MTT assay 19447618

Literature References

PubMed DOI Target Context # Activities
28256373 10.1016/j.bmcl.2017.02.038 RAW264.7 9
32975953 10.1021/acs.jnatprod.0c00699 MV4-11 3
19447618 10.1016/j.bmcl.2009.04.129 RAW264.7 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 Voltage-gated inwardly rectifying potassium channel KCNH2 2
28064141 10.1016/j.ejmech.2016.12.017 A549 2
28064141 10.1016/j.ejmech.2016.12.017 Cytochrome P450 1A2 2
28064141 10.1016/j.ejmech.2016.12.017 Cytochrome P450 2C9 2
28064141 10.1016/j.ejmech.2016.12.017 Cytochrome P450 3A4 2
22727643 10.1016/j.bmcl.2012.05.112 Staphylococcus aureus 2
28064141 10.1016/j.ejmech.2016.12.017 Cytochrome P450 2C19 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 Cytochrome P450 2D6 2
32975953 10.1021/acs.jnatprod.0c00699 K562 2
23786711 10.1016/j.ejmech.2013.05.015 ADMET 1
23786711 10.1016/j.ejmech.2013.05.015 Unchecked 1
23786711 10.1016/j.ejmech.2013.05.015 Amyloid-beta precursor protein 1
32208222 10.1016/j.ejmech.2020.112216 RAW264.7 1
19447618 10.1016/j.bmcl.2009.04.129 HeLa 1

Data from ChEMBL 36 via Core Engine