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Compound Detail

CHEMBL221960

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COc1cc(/C=C/C(=O)O)ccc1OC/C=C(\C)CCC=C(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL221960
Phase Preclinical
Structure Type MOL
InChI Key WAHYZVVZFNUXSC-TWGDSDBMSA-N
5
Targets
6
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

330.4
MW (Da)
4.86
ALogP
3
HBA
1
HBD
55.8
PSA (Ų)
0.52
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H26O4
MW 330.42
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness 1.32

Activity Summary

IC50 5 meas. best 5.6
Ki 1 meas. best 4.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 5.6 5.6 2500.0 1
BT-549
CHEMBL614072
 IC50 5.25 5.25 5600.0 1
MDA-MB-231
CHEMBL400
 IC50 4.66 4.66 22000.0 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 4.27 4.27 54200.0 1
Melatonin receptor type 1A
CHEMBL1945
 Ki 4.23 4.23 59000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 2500.0 nM 5.6 Antiproliferative activity against mouse mammary carcinoma cell after 24 hrs by ... 29144746
BT-549 IC50 = 5600.0 nM 5.25 Antiproliferative activity against human BT549 cells after 24 hrs by MTT assay 29144746
MDA-MB-231 IC50 = 22000.0 nM 4.66 Antiproliferative activity against human MDA-MB-231 cells after 24 hrs by MTT as... 29144746
Prostaglandin G/H synthase 1 IC50 = 54200.0 nM 4.27 Inhibition of ovine COX1 using TMPD as substrate preincubated for 15 mins 21843935
Melatonin receptor type 1A Ki = 59000.0 nM 4.23 Displacement of 2-[125I]iodomelatonin from human MT1 receptor expressed in CHO c... 29144746

Literature References

PubMed DOI Target Context # Activities
18093697 10.1016/j.ejmech.2007.11.001 Porphyromonas gingivalis 8
22472691 10.1016/j.bmcl.2012.03.057 Bile acid receptor 8
19679472 10.1016/j.bmcl.2009.07.110 Mus musculus 7
21696954 10.1016/j.bmcl.2011.05.089 NON-PROTEIN TARGET 4
21843935 10.1016/j.bmcl.2011.07.040 NON-PROTEIN TARGET 3
28525281 10.1021/acs.jnatprod.7b00173 Aryl hydrocarbon receptor 2
29144746 10.1021/acs.jnatprod.7b00853 BT-549 2
29144746 10.1021/acs.jnatprod.7b00853 MDA-MB-231 2
29144746 10.1021/acs.jnatprod.7b00853 Unchecked 2
23566521 10.1016/j.bmcl.2013.03.050 RAW264.7 2
18093697 10.1016/j.ejmech.2007.11.001 Streptococcus mutans 2
21696954 10.1016/j.bmcl.2011.05.089 LoVo 1
21843935 10.1016/j.bmcl.2011.07.040 Prostaglandin G/H synthase 1 1
21843935 10.1016/j.bmcl.2011.07.040 Prostaglandin G/H synthase 2 1
21696954 10.1016/j.bmcl.2011.05.089 SK-MEL-28 1
21696954 10.1016/j.bmcl.2011.05.089 PC-3 1
29144746 10.1021/acs.jnatprod.7b00853 Melatonin receptor type 1A 1
21696954 10.1016/j.bmcl.2011.05.089 A549 1
17768049 10.1016/j.bmcl.2007.07.058 Mus musculus 1
26905390 10.1021/acs.jnatprod.5b00396 Transient receptor potential cation channel subfamily A member 1 1

Data from ChEMBL 36 via Core Engine