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Compound Detail

CHEMBL298240

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COc1cc2c(c(OC)c1OC)-c1ccc(SC)c(=O)cc1[C@@H](N)CC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL298240
Phase Preclinical
Structure Type MOL
InChI Key NUNCOHUMTCDISK-AWEZNQCLSA-N
16
Targets
30
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

373.5
MW (Da)
3.41
ALogP
6
HBA
1
HBD
70.8
PSA (Ų)
0.83
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 C20H23NO4S
MW 373.47
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.94

Activity Summary

IC50 29 meas. best 8.89
EC50 1 meas. best 7.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
SK-OV-3
CHEMBL614925
 IC50 8.89 8.455 1.3 2
MDA-MB-231
CHEMBL400
 IC50 8.66 7.28 2.2 2
MCF7
CHEMBL387
 IC50 8.02 6.855 9.5 4
LoVo
CHEMBL614721
 IC50 7.99 7.25 10.3 3
A549
CHEMBL392
 IC50 7.96 7.79 11.0 2
Human immunodeficiency virus 1
CHEMBL378
 IC50 7.89 7.89 13.0 1
H9
CHEMBL614806
 EC50 7.89 7.89 13.0 1
BALB/3T3
CHEMBL613876
 IC50 7.81 7.23 15.4 2
Unchecked
CHEMBL612545
 IC50 7.79 6.7 16.3 5
IGROV-1
CHEMBL613984
 IC50 7.64 7.64 23.0 1
L1210
CHEMBL386
 IC50 7.4 7.4 40.0 1
DLD-1
CHEMBL614285
 IC50 5.93 5.93 1180.0 1
Tubulin
CHEMBL2095182
 IC50 5.89 5.89 1300.0 2
Tubulin alpha chain
CHEMBL3658
 IC50 5.88 5.88 1318.3 1
Tubulin beta chain
CHEMBL3394
 IC50 5.7 5.7 2000.0 1
CA46
CHEMBL612566
 IC50 4.42 4.42 38000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
SK-OV-3 IC50 = 1.3 nM 8.89 Cytotoxicity against human SKOV3 cells assessed as inhibition of cell proliferat... 30429975
MDA-MB-231 IC50 = 2.2 nM 8.66 Anti tumor activity on human breast cancer cell line MDR-negative MDA-MB 231 aft... 10602712
SK-OV-3 IC50 = 9.6 nM 8.02 Cytotoxicity against arrested non-proliferative human SKOV3 cells assessed as in... 30429975
MCF7 IC50 = 9.5 nM 8.02 Antiproliferative activity against human MCF7 cells assessed as inhibition of ce... 34592435
LoVo IC50 = 10.3 nM 7.99 Antiproliferative activity against human LoVo cells assessed as inhibition of ce... 34592435
A549 IC50 = 11.0 nM 7.96 Antiproliferative activity against human A549 cells assessed as inhibition of ce... 34592435
Human immunodeficiency virus 1 IC50 = 13.0 nM 7.89 Antiviral activity against HIV1 HTLV-3B in human H9 cells after 3 days by p24 an... 1919593
H9 EC50 = 13.0 nM 7.89 Cytotoxicity against human H9 cells 1919593
MCF7 IC50 = 14.2 nM 7.85 Antiproliferative activity against human MCF-7 cells incubated for 72 hrs by SRB... 33465696
BALB/3T3 IC50 = 15.4 nM 7.81 Cytotoxicity against mouse BALB/3T3 cells assessed as reduction in cell viabilit... 34592435
Unchecked IC50 = 16.3 nM 7.79 Antiproliferative activity against human ALL5 cells incubated for 120 hrs follow... 33465696
LoVo IC50 = 16.9 nM 7.77 Antiproliferative activity against human LoVo cells incubated for 72 hrs by SRB ... 33465696
IGROV-1 IC50 = 23.0 nM 7.64 Antiproliferative activity against human IGROV1 cells assessed as growth inhibit... 19833515
A549 IC50 = 24.1 nM 7.62 Antiproliferative activity against human A549 cells incubated for 72 hrs by SRB ... 33465696
L1210 IC50 = 40.0 nM 7.4 In vitro cytotoxicity against L1210 (murine leukemia) cells. 2299625
Unchecked IC50 = 77.8 nM 7.11 Antiproliferative activity against human Lovo/DX cells assessed as inhibition of... 34592435
Unchecked IC50 = 145.0 nM 6.84 Antiproliferative activity against doxorubicin-resistant human LoVo/DX cells inc... 33465696
BALB/3T3 IC50 = 223.0 nM 6.65 Antiproliferative activity against mouse BALB/3T3 cells incubated for 72 hrs by ... 33465696
MCF7 IC50 = 670.0 nM 6.17 Cytotoxicity against human MCF7 cells assessed as inhibition of cell proliferati... 30429975
Unchecked IC50 = 910.0 nM 6.04 Inhibition of tubulin assembly 20542428

Literature References

PubMed DOI Target Context # Activities
33465696 10.1016/j.bmc.2021.116014 Unchecked 3
7241524 10.1021/jm00137a031 Mus musculus 3
20542428 10.1016/j.bmcl.2010.05.081 Unchecked 3
30429975 10.1039/C8MD00352A SK-OV-3 2
7265111 10.1021/jm00135a004 No relevant target 1
20542428 10.1016/j.bmcl.2010.05.081 DU-145 1
20542428 10.1016/j.bmcl.2010.05.081 A549 1
34592435 10.1016/j.bmcl.2021.128382 BALB/3T3 1
19833515 10.1016/j.bmcl.2009.09.075 IGROV-1 1
1919593 10.1021/np50074a052 H9 1
1919593 10.1021/np50074a052 Human immunodeficiency virus 1 1
7265111 10.1021/jm00135a004 P388 1
10649972 10.1021/jm990333a Tubulin alpha chain 1
2299625 10.1021/jm00164a015 L1210 1
2299625 10.1021/jm00164a015 Tubulin beta chain 1
10602712 10.1021/jm981134e MCF7 1
10602712 10.1021/jm981134e MDA-MB-231 1
7241524 10.1021/jm00137a031 No relevant target 1
9083485 10.1021/jm960663k CA46 1
9083485 10.1021/jm960663k Tubulin alpha chain 1

Data from ChEMBL 36 via Core Engine