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Compound Detail

CHEMBL243263

6-HYDROXYCOUMARIN
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O=c1ccc2cc(O)ccc2o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL243263
Name 6-HYDROXYCOUMARIN
Phase Preclinical
Structure Type MOL
InChI Key CJIJXIFQYOPWTF-UHFFFAOYSA-N
8
Targets
15
Activities
2
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 0.92

Activity Summary

IC50 10 meas. best 6.35
Ki 5 meas. best 7.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 9
CHEMBL3594
 Ki 7.52 7.12 30.5 2
Carbonic anhydrase 12
CHEMBL3242
 Ki 7.47 6.82 33.9 2
SK-MEL-28
CHEMBL614919
 IC50 6.35 6.35 450.0 1
SK-MEL3
CHEMBL614920
 IC50 5.94 5.835 1140.0 2
Unchecked
CHEMBL612545
 IC50 5.53 5.53 2950.0 1
Induced myeloid leukemia cell differentiation protein Mcl-1
CHEMBL4361
 Ki 4.62 4.62 23860.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.46 4.395 35000.0 2
COLO 205
CHEMBL614561
 IC50 4.41 4.41 38700.0 1
Induced myeloid leukemia cell differentiation protein Mcl-1
CHEMBL4361
 IC50 4.08 4.08 83690.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 9 Ki = 30.5 nM 7.52 Inhibition of human carbonic anhydrase 9 incubated for 15 mins prior to testing ... 29197732
Carbonic anhydrase 12 Ki = 33.9 nM 7.47 Inhibition of human carbonic anhydrase 12 incubated for 15 mins prior to testing... 29197732
Carbonic anhydrase 9 Ki = 190.0 nM 6.72 Inhibition of human carbonic anhydrase 9 catalytic domain by Stopped-Flow CO2 Hy... 26688270
SK-MEL-28 IC50 = 450.0 nM 6.35 Anticancer activity against human SK-MEL-28 cells assessed as reduction in cell ... 37197457
Carbonic anhydrase 12 Ki = 680.0 nM 6.17 Inhibition of human carbonic anhydrase 12 catalytic domain by Stopped-Flow CO2 H... 26688270
SK-MEL3 IC50 = 1140.0 nM 5.94 Anticancer activity against human SK-MEL3 cells assessed as reduction in cell vi... 37197457
SK-MEL3 IC50 = 1850.0 nM 5.73 Anticancer activity against human SK-MEL3 cells assessed as reduction in cell vi... 37197457
Unchecked IC50 = 2950.0 nM 5.53 Cytotoxicity against human C3PV cells assessed as reduction in cell viability in... 37197457
Induced myeloid leukemia cell differentiation protein Mcl-1 Ki = 23860.0 nM 4.62 Displacement of FAM-Bid peptide from recombinant N-terminal His6x-tagged human M... 33218896
NON-PROTEIN TARGET IC50 = 35000.0 nM 4.46 Cytotoxicity against human HL60 cells after 48 hrs by MTT assay 25088398
COLO 205 IC50 = 38700.0 nM 4.41 Cytotoxicity against human COLO205 cells after 48 hrs by MTT assay 25088398
NON-PROTEIN TARGET IC50 = 46200.0 nM 4.33 Cytotoxicity against human HCT116 cells after 48 hrs by MTT assay 25088398
Induced myeloid leukemia cell differentiation protein Mcl-1 IC50 = 83690.0 nM 4.08 Displacement of FAM-Bid peptide from recombinant N-terminal His6x-tagged human M... 33218896

Literature References

PubMed DOI Target Context # Activities
23306152 10.3390/ijms14011293 Aspergillus fumigatus 5
23306152 10.3390/ijms14011293 Aspergillus flavus 4
25088398 10.1016/j.bmcl.2014.07.031 NON-PROTEIN TARGET 3
29236486 10.1021/acs.jnatprod.7b00665 A549 3
29236486 10.1021/acs.jnatprod.7b00665 Influenza A virus 3
20805028 10.1016/j.bmcl.2010.08.038 Unchecked 3
37197457 10.1021/acsmedchemlett.3c00019 Unchecked 2
37197457 10.1021/acsmedchemlett.3c00019 SK-MEL3 2
25205194 10.1016/j.bmcl.2014.08.038 NON-PROTEIN TARGET 2
33218896 10.1016/j.bmc.2020.115851 Induced myeloid leukemia cell differentiation protein Mcl-1 2
21053896 10.1021/jm100757r Unchecked 1
20805028 10.1016/j.bmcl.2010.08.038 Aldo-keto reductase family 1 member B1 1
37197457 10.1021/acsmedchemlett.3c00019 SK-MEL-28 1
25088398 10.1016/j.bmcl.2014.07.031 COLO 205 1
25088398 10.1016/j.bmcl.2014.07.031 A549 1
26519930 10.1016/j.ejmech.2015.10.029 Nuclear factor erythroid 2-related factor 2 1
26519930 10.1016/j.ejmech.2015.10.029 No relevant target 1
26688270 10.1021/acs.jmedchem.5b01720 Carbonic anhydrase 2 1
26688270 10.1021/acs.jmedchem.5b01720 Carbonic anhydrase 9 1
20580555 10.1016/j.bmcl.2010.06.040 Carbonic anhydrase 1 1

Data from ChEMBL 36 via Core Engine