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Compound Detail

CHEMBL156692

7-PRENYLOXYCOUMARIN
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CC(C)=CCOc1ccc2ccc(=O)oc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL156692
Name 7-PRENYLOXYCOUMARIN
Phase Preclinical
Structure Type MOL
InChI Key SMHJTSOVVRGDEO-UHFFFAOYSA-N
5
Targets
7
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

230.3
MW (Da)
3.14
ALogP
3
HBA
0
HBD
39.4
PSA (Ų)
0.60
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C14H14O3
MW 230.26
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness 0.93

Activity Summary

IC50 6 meas. best 4.52
Ki 1 meas. best 5.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Melatonin receptor type 1A
CHEMBL1945
 Ki 5.28 5.28 5200.0 1
LoVo
CHEMBL614721
 IC50 4.52 4.305 30000.0 2
BT-549
CHEMBL614072
 IC50 4.43 4.43 37000.0 1
Unchecked
CHEMBL612545
 IC50 4.3 4.26 50300.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.1 4.1 79000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Melatonin receptor type 1A Ki = 5200.0 nM 5.28 Displacement of 2-[125I]iodomelatonin from human MT1 receptor expressed in CHO c... 29144746
LoVo IC50 = 30000.0 nM 4.52 Growth inhibition of human LoVo cells after 24 hrs by MTT assay 28109950
BT-549 IC50 = 37000.0 nM 4.43 Antiproliferative activity against human BT549 cells after 24 hrs by MTT assay 29144746
Unchecked IC50 = 50300.0 nM 4.3 Growth inhibition of human LoVo/DX cells after 24 hrs by MTT assay 28109950
Unchecked IC50 = 60400.0 nM 4.22 Inhibition of soybean 15-lipoxygenase by MBTH-DMAB method 23047230
NON-PROTEIN TARGET IC50 = 79000.0 nM 4.1 Cytotoxicity against human OE21 cells after 72 hrs by MTT assay 21696954
LoVo IC50 = 82000.0 nM 4.09 Cytotoxicity against human LoVo cells after 72 hrs by MTT assay 21696954

Literature References

PubMed DOI Target Context # Activities
29730190 10.1016/j.ejmech.2018.04.051 Melan-a 14
19679472 10.1016/j.bmcl.2009.07.110 Mus musculus 8
22472691 10.1016/j.bmcl.2012.03.057 Bile acid receptor 8
10543892 10.1021/np990048u Salmonella typhimurium 6
23306152 10.3390/ijms14011293 Aspergillus fumigatus 5
21696954 10.1016/j.bmcl.2011.05.089 NON-PROTEIN TARGET 4
23306152 10.3390/ijms14011293 Aspergillus flavus 4
28844340 10.1016/j.ejmech.2017.08.038 Mus musculus 3
21880488 10.1016/j.bmcl.2011.08.005 PANC-1 2
29144746 10.1021/acs.jnatprod.7b00853 BT-549 2
28525281 10.1021/acs.jnatprod.7b00173 Aryl hydrocarbon receptor 2
28109950 10.1016/j.ejmech.2017.01.020 Unchecked 2
25205194 10.1016/j.bmcl.2014.08.038 NON-PROTEIN TARGET 2
22222157 10.1016/j.bmc.2011.12.002 Beta-secretase 1 2
29730190 10.1016/j.ejmech.2018.04.051 No relevant target 2
29730190 10.1016/j.ejmech.2018.04.051 Estrogen receptor beta 2
23047230 10.1016/j.ejmech.2012.09.006 Unchecked 1
10636244 10.1016/s0960-894x(99)00578-8 Mus musculus 1
21696954 10.1016/j.bmcl.2011.05.089 LoVo 1
21696954 10.1016/j.bmcl.2011.05.089 PC-3 1

Data from ChEMBL 36 via Core Engine