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Compound Detail

CHEMBL301141

4-HYDROXYCOUMARINS
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O=c1cc(O)c2ccccc2o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL301141
Name 4-HYDROXYCOUMARINS
Phase Preclinical
Structure Type MOL
InChI Key VXIXUWQIVKSKSA-UHFFFAOYSA-N
7
Targets
19
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

162.1
MW (Da)
1.50
ALogP
3
HBA
1
HBD
50.4
PSA (Ų)
0.60
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C9H6O3
MW 162.14
Aromatic Rings 2
Heavy Atoms 12
NP-Likeness 0.56

Activity Summary

EC50 9 meas.
IC50 7 meas. best 6.22
Ki 3 meas. best 6.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 9
CHEMBL3594
 Ki 6.39 6.39 410.0 1
Unchecked
CHEMBL612545
 IC50 6.22 5.305 600.0 2
SK-MEL-28
CHEMBL614919
 IC50 5.89 5.89 1300.0 1
SK-MEL3
CHEMBL614920
 IC50 5.68 5.68 2100.0 1
Carbonic anhydrase 12
CHEMBL3242
 Ki 5.2 5.2 6300.0 1
B16-F10
CHEMBL612656
 IC50 4.15 4.15 70740.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 4.02 4.02 95000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 9 Ki = 410.0 nM 6.39 Inhibition of human carbonic anhydrase 9 catalytic domain by Stopped-Flow CO2 Hy... 26688270
Unchecked IC50 = 600.0 nM 6.22 Cytotoxicity against human C3PV cells assessed as reduction in cell viability in... 37197457
SK-MEL-28 IC50 = 1300.0 nM 5.89 Anticancer activity against human SK-MEL-28 cells assessed as reduction in cell ... 37197457
SK-MEL3 IC50 = 2100.0 nM 5.68 Anticancer activity against human SK-MEL3 cells assessed as reduction in cell vi... 37197457
Carbonic anhydrase 12 Ki = 6300.0 nM 5.2 Inhibition of human carbonic anhydrase 12 catalytic domain by Stopped-Flow CO2 H... 26688270
Unchecked IC50 = 40500.0 nM 4.39 Inhibition kidney aldose reductase 2 by spectrophotometric analysis 20805028
B16-F10 IC50 = 70740.0 nM 4.15 Cytotoxicity against mouse B16F10 cells assessed as reduction in cell viability 30594028
Carbonic anhydrase 1 Ki = 95000.0 nM 4.02 Inhibition of human carbonic anhydrase 1 by Stopped-Flow CO2 Hydrase assay 26688270

Literature References

PubMed DOI Target Context # Activities
28041801 10.1016/j.bmc.2016.12.025 NON-PROTEIN TARGET 9
23306152 10.3390/ijms14011293 Aspergillus fumigatus 5
24721833 10.1016/j.bmc.2014.03.026 MCF7 4
23306152 10.3390/ijms14011293 Aspergillus flavus 4
24721833 10.1016/j.bmc.2014.03.026 LNCaP 4
24721833 10.1016/j.bmc.2014.03.026 PC-3 3
24721833 10.1016/j.bmc.2014.03.026 U-937 3
24721833 10.1016/j.bmc.2014.03.026 MDA-MB-231 3
20805028 10.1016/j.bmcl.2010.08.038 Unchecked 3
9083481 10.1021/jm960754h Human immunodeficiency virus type 1 integrase 2
21964183 10.1016/j.bmc.2011.09.012 NON-PROTEIN TARGET 2
22832320 10.1016/j.bmcl.2012.07.013 NON-PROTEIN TARGET 2
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 1A10 2
38283214 10.1039/d3md00511a MDA-MB-231 2
37197457 10.1021/acsmedchemlett.3c00019 Unchecked 2
24721833 10.1016/j.bmc.2014.03.026 ADMET 2
9003523 10.1021/jm960450v Human immunodeficiency virus type 1 integrase 2
20580555 10.1016/j.bmcl.2010.06.040 Carbonic anhydrase 1 1
38340509 10.1016/j.ejmech.2024.116179 T98G 1
17316915 10.1016/j.ejmech.2006.12.023 Xanthine dehydrogenase/oxidase 1

Data from ChEMBL 36 via Core Engine