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Compound Detail

CHEMBL182653

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

Basic Information

ChEMBL ID CHEMBL182653
Phase Preclinical
Structure Type MOL
InChI Key ADRQFDIWPRFKSP-RUDMXATFSA-N
3
Targets
4
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

270.3
MW (Da)
3.00
ALogP
4
HBA
2
HBD
66.8
PSA (Ų)
0.66
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 C16H14O4
MW 270.28
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.54

Activity Summary

IC50 4 meas. best 6.03

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aldo-keto reductase family 1 member B1
CHEMBL2622
 IC50 6.03 6.03 930.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 4.92 4.7 12050.0 2
Human immunodeficiency virus type 1 integrase
CHEMBL3471
 IC50 4.41 4.41 39000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aldo-keto reductase family 1 member B1 IC50 = 930.0 nM 6.03 Inhibition of Rattus norvegicus (rat) lens aldose reductase -
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 12050.0 nM 4.92 Inhibition of human BCRP expressed in MDCK2 cells assessed as Hoechst 33342 accu... 22112540
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 33320.0 nM 4.48 Inhibition of BCRP in human MCF7/MX cells assessed as Hoechst 33342 accumulation... 22112540
Human immunodeficiency virus type 1 integrase IC50 = 39000.0 nM 4.41 Inhibition of HIV1 integrase strand transfer activity 17502148

Literature References

PubMed DOI Target Context # Activities
28235703 10.1016/j.ejmech.2017.02.037 Bile acid receptor 3
22743086 10.1016/j.bmc.2012.05.062 MDCK 3
22112540 10.1016/j.bmc.2011.10.074 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
30852084 10.1016/j.bmcl.2019.02.028 GroEL/GroES 2
33006891 10.1021/acs.jnatprod.0c00728 Unchecked 2
15225696 10.1016/j.bmcl.2004.05.071 Leishmania donovani 2
19807106 10.1021/jm900964r Peroxisome proliferator-activated receptor gamma 2
17502148 10.1016/j.bmc.2007.04.041 Human immunodeficiency virus type 1 integrase 2
22177409 10.1016/j.bmc.2011.11.042 MCF7 1
22177409 10.1016/j.bmc.2011.11.042 NCI-H460 1
22177409 10.1016/j.bmc.2011.11.042 NON-PROTEIN TARGET 1
18603336 10.1016/j.ejmech.2008.05.032 MCF7 1
22112540 10.1016/j.bmc.2011.10.074 ATP-dependent translocase ABCB1 1
22112540 10.1016/j.bmc.2011.10.074 Multidrug resistance-associated protein 1 1
22608392 10.1016/j.bmcl.2012.04.108 3T3-L1 1
18603336 10.1016/j.ejmech.2008.05.032 Radical scavenging activity 1
- 10.1007/s00044-009-9202-z Mus musculus 1
- 10.1007/s00044-012-0367-5 Aldo-keto reductase family 1 member B1 1
23369537 10.1016/j.bmcl.2012.12.096 HEK293 1
18603336 10.1016/j.ejmech.2008.05.032 NON-PROTEIN TARGET 1

Data from ChEMBL 36 via Core Engine