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Compound Detail

CHEMBL77198

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COc1ccc2c(=O)c(O)c(-c3ccc(OC)c(OC)c3)oc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL77198
Phase Preclinical
Structure Type MOL
InChI Key KSAJVJYHNOORPX-UHFFFAOYSA-N
6
Targets
8
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

328.3
MW (Da)
3.19
ALogP
6
HBA
1
HBD
78.1
PSA (Ų)
0.79
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 C18H16O6
MW 328.32
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness 0.59

Activity Summary

IC50 6 meas. best 6.0
EC50 2 meas. best 5.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 6.0 5.875 1010.0 2
Trypanosoma brucei brucei
CHEMBL612851
 EC50 5.52 5.52 2990.0 2
PC-3
CHEMBL390
 IC50 4.7 4.7 19900.0 1
MCF-10A
CHEMBL614321
 IC50 4.62 4.62 23950.0 1
LNCaP
CHEMBL612518
 IC50 4.61 4.61 24500.0 1
DU-145
CHEMBL613508
 IC50 4.6 4.6 24900.0 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 = 1010.0 nM 6.0 Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of Ho... 23851114
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 1770.0 nM 5.75 Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of ph... 23851114
Trypanosoma brucei brucei EC50 = 2990.0 nM 5.52 Anti-parasitic activity against bloodstream form of Trypanosoma brucei brucei Li... 28064141
Trypanosoma brucei brucei EC50 = 2990.0 nM 5.52 Antitrypanosomal activity against Trypanosoma brucei brucei Lister 427 bloodstre... 27411733
PC-3 IC50 = 19900.0 nM 4.7 Antiproliferative activity against human PC3 cells after 3 days by WST-1 assay 30165345
MCF-10A IC50 = 23950.0 nM 4.62 Cytotoxicity against human MCF10A cells assessed as decrease in cell viability a... 30165345
LNCaP IC50 = 24500.0 nM 4.61 Antiproliferative activity against human LNCAP cells after 3 days by WST-1 assay 30165345
DU-145 IC50 = 24900.0 nM 4.6 Antiproliferative activity against human DU145 cells after 3 days by WST-1 assay 30165345

Literature References

PubMed DOI Target Context # Activities
30165345 10.1016/j.ejmech.2018.08.047 PC-3 8
23851114 10.1016/j.ejmech.2013.06.035 MDCK 4
9632366 10.1021/jm970842h Tubulin 2
23851114 10.1016/j.ejmech.2013.06.035 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
25027933 10.1016/j.bmcl.2014.06.061 RAW264.7 2
27411733 10.1021/acs.jmedchem.6b00698 Trypanosoma brucei brucei 2
27411733 10.1021/acs.jmedchem.6b00698 Cytochrome P450 1A2 1
9632366 10.1021/jm970842h Panel NCI-60 (60 carcinoma cell lines) 1
27411733 10.1021/acs.jmedchem.6b00698 Unchecked 1
27411733 10.1021/acs.jmedchem.6b00698 THP-1 1
27411733 10.1021/acs.jmedchem.6b00698 WI-38 1
27411733 10.1021/acs.jmedchem.6b00698 A549 1
27411733 10.1021/acs.jmedchem.6b00698 786-0 1
30165345 10.1016/j.ejmech.2018.08.047 PWR-1E 1
30165345 10.1016/j.ejmech.2018.08.047 MCF-10A 1
30165345 10.1016/j.ejmech.2018.08.047 LNCaP 1
30165345 10.1016/j.ejmech.2018.08.047 DU-145 1
28064141 10.1016/j.ejmech.2016.12.017 Unchecked 1
28064141 10.1016/j.ejmech.2016.12.017 Trypanosoma brucei brucei 1
469554 10.1021/np50001a002 L1210 1

Data from ChEMBL 36 via Core Engine