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Compound Detail

CHEMBL77966

RETUSIN
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COc1cc(O)c2c(=O)c(OC)c(-c3ccc(OC)c(OC)c3)oc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL77966
Name RETUSIN
Phase Preclinical
Structure Type MOL
InChI Key HHGPYJLEJGNWJA-UHFFFAOYSA-N
12
Targets
20
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

358.4
MW (Da)
3.20
ALogP
7
HBA
1
HBD
87.4
PSA (Ų)
0.75
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 C19H18O7
MW 358.35
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness 0.99

Activity Summary

IC50 19 meas. best 6.42
EC50 1 meas. best 6.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
M14
CHEMBL614317
 IC50 6.42 6.42 380.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.41 5.28 390.0 4
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 6.41 6.2425 390.0 4
SARS-CoV-2
CHEMBL4303835
 EC50 6.22 6.22 600.0 1
Unchecked
CHEMBL612545
 IC50 4.92 4.92 12000.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 4.8 4.8 16000.0 1
HeLa
CHEMBL399
 IC50 4.33 4.33 46370.0 1
Multidrug resistance-associated protein 1
CHEMBL3004
 IC50 4.3 4.3 50000.0 1
A-431
CHEMBL614069
 IC50 4.24 4.16 57540.0 2
HCT-15
CHEMBL612263
 IC50 4.17 4.17 68110.0 1
A-375
CHEMBL613859
 IC50 4.16 4.16 69720.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.13 4.13 73300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
M14 IC50 = 380.0 nM 6.42 Anticancer activity against human M14 cells by HTS assay 25139569
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 390.0 nM 6.41 Inhibition of BCRP expressed in MDCK cells using Hoechst 33342 staining 21354800
NON-PROTEIN TARGET IC50 = 390.0 nM 6.41 Anticancer activity against human LOXIMVI cells by HTS assay 25139569
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 540.0 nM 6.27 Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of Ho... 23851114
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 570.0 nM 6.24 Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of ph... 23851114
SARS-CoV-2 EC50 = 600.0 nM 6.22 Antiviral activity against SARS-CoV-2 infected in human Calu-3 cells assessed as... 37257024
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 900.0 nM 6.05 Inhibition of BCRP expressed in MCF-7 MX cells using Hoechst 33342 staining 21354800
NON-PROTEIN TARGET IC50 = 6530.0 nM 5.18 Anticancer activity against human Calu1 cells by HTS assay 25139569
NON-PROTEIN TARGET IC50 = 10460.0 nM 4.98 Anticancer activity against human H1299 cells by HTS assay 25139569
Unchecked IC50 = 12000.0 nM 4.92 Inhibition of P-gp expressed in A2780adr cells by calcein AM accumulation assay 21354800
ATP-dependent translocase ABCB1 IC50 = 16000.0 nM 4.8 Inhibition of MDR1 expressed in MDCK cells using rhodamine 123 staining by flow ... 21354800
NON-PROTEIN TARGET IC50 = 28000.0 nM 4.55 Cytotoxicity against human HL60 cells after 72 hrs by MTT assay 25014747
HeLa IC50 = 46370.0 nM 4.33 Anticancer activity against human HeLa cells by HTS assay 25139569
Multidrug resistance-associated protein 1 IC50 = 50000.0 nM 4.3 Inhibition of MRP1 expressed in human 2008 cells assessed as calcein AM accumula... 21354800
A-431 IC50 = 57540.0 nM 4.24 Cytotoxicity against human A431 cells assessed as cell growth inhibition after 7... 25906385
HCT-15 IC50 = 68110.0 nM 4.17 Cytotoxicity against human HCT15 cells assessed as cell growth inhibition after ... 25906385
A-375 IC50 = 69720.0 nM 4.16 Cytotoxicity against human A375 cells assessed as cell growth inhibition after 7... 25906385
Plasmodium falciparum IC50 = 73300.0 nM 4.13 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum NF54 16722653
A-431 IC50 = 82250.0 nM 4.08 Cytotoxicity against cisplatin-resistant human A431 cells assessed as cell growt... 25906385

Literature References

PubMed DOI Target Context # Activities
25139569 10.1016/j.bmcl.2014.08.006 NON-PROTEIN TARGET 9
35143982 10.1016/j.bmcl.2022.128608 Unchecked 8
25906385 10.1021/acs.jmedchem.5b00230 HEK293 8
22647223 10.1016/j.ejmech.2012.04.044 Thrombin 4
21493073 10.1016/j.bmc.2011.03.040 3T3-L1 4
23851114 10.1016/j.ejmech.2013.06.035 MDCK 4
25906385 10.1021/acs.jmedchem.5b00230 A-431 3
33038547 10.1016/j.bmcl.2020.127606 Unchecked 3
23851114 10.1016/j.ejmech.2013.06.035 Broad substrate specificity ATP-binding cassette transporter ABCG2 3
25906385 10.1021/acs.jmedchem.5b00230 NON-PROTEIN TARGET 3
18163582 10.1021/np0704349 NON-PROTEIN TARGET 2
22961680 10.1124/dmd.112.047142 ADMET 2
16722653 10.1021/jm0600545 Plasmodium falciparum 2
21354800 10.1016/j.bmc.2010.12.043 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
21354800 10.1016/j.bmc.2010.12.043 Unchecked 2
22743241 10.1016/j.ejmech.2012.05.026 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
22743241 10.1016/j.ejmech.2012.05.026 ADMET 2
1847431 10.1021/jm00106a039 Enterovirus C 2
37257024 10.1021/acs.jnatprod.3c00249 SARS-CoV-2 1
469554 10.1021/np50001a002 CA-755 1

Data from ChEMBL 36 via Core Engine