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Compound Detail

CHEMBL150372

3-HYDROXYCOUMARIN
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O=c1oc2ccccc2cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL150372
Name 3-HYDROXYCOUMARIN
Phase Preclinical
Structure Type MOL
InChI Key MJKVTPMWOKAVMS-UHFFFAOYSA-N
8
Targets
24
Activities
4
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 0.50

Activity Summary

IC50 14 meas. best 7.46
Ki 6 meas. best 7.89
Kd 3 meas. best 5.4
EC50 1 meas. best 4.18

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D-amino-acid oxidase
CHEMBL5485
 Ki 7.89 6.6775 13.0 4
D-amino-acid oxidase
CHEMBL5485
 IC50 7.46 6.6167 34.7 3
SK-MEL-28
CHEMBL614919
 IC50 5.92 5.92 1200.0 1
Mushroom tyrosinase
CHEMBL6066154
 IC50 5.6 5.6 2490.0 1
Tyrosinase
CHEMBL1973
 Ki 5.47 5.47 3400.0 2
D-amino-acid oxidase
CHEMBL5485
 Kd 5.4 5.2833 4000.0 3
SK-MEL3
CHEMBL614920
 IC50 5.17 5.17 6800.0 1
Unchecked
CHEMBL612545
 IC50 4.9 4.675 12530.0 2
Tyrosinase
CHEMBL1973
 IC50 4.58 4.58 26000.0 1
Aldo-keto reductase family 1 member B1
CHEMBL1900
 IC50 4.21 4.21 62000.0 1
No relevant target
CHEMBL2362975
 EC50 4.18 4.18 65800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D-amino-acid oxidase Ki = 13.0 nM 7.89 Competitive inhibition of human recombinant DAAO by Michaelis-Menten plot analys... 23631755
D-amino-acid oxidase IC50 = 34.67 nM 7.46 Competitive inhibition of human recombinant DAAO after 1 hr by coupled enzyme as... 23631755
D-amino-acid oxidase Ki = 156.0 nM 6.81 Inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherich... 23391306
D-amino-acid oxidase Ki = 265.0 nM 6.58 Inhibition of human recombinant N-terminal His-tagged DAO Y224F mutant expressed... 23391306
D-amino-acid oxidase IC50 = 440.0 nM 6.36 Inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherich... 23391306
D-amino-acid oxidase IC50 = 943.0 nM 6.03 Inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherich... 23391306
SK-MEL-28 IC50 = 1200.0 nM 5.92 Anticancer activity against human SK-MEL-28 cells assessed as reduction in cell ... 37197457
Mushroom tyrosinase IC50 = 2490.0 nM 5.6 Inhibition of mushroom tyrosinase using L-DOPA as substrate by spectrophotometri... 38823727
Tyrosinase Ki = 3400.0 nM 5.47 Binding affinity to human Tyrosinase using L-DOPA as substrate assessed as inhib... 37487307
Tyrosinase Ki = 3400.0 nM 5.47 Inhibition of human tyrosinase expressed in Escherichia coli 32787103
D-amino-acid oxidase Ki = 3690.0 nM 5.43 Inhibition of human recombinant N-terminal His-tagged DAO Y224A mutant expressed... 23391306
D-amino-acid oxidase Kd = 4000.0 nM 5.4 Binding affinity to human recombinant DAAO at 443 nm spectral modification by sp... 23631755
D-amino-acid oxidase Kd = 5600.0 nM 5.25 Binding affinity to human recombinant DAAO at 496 nm spectral modification by sp... 23631755
D-amino-acid oxidase Kd = 6300.0 nM 5.2 Binding affinity to human recombinant DAAO by stopped flow spectrophotometric an... 23631755
SK-MEL3 IC50 = 6800.0 nM 5.17 Anticancer activity against human SK-MEL3 cells assessed as reduction in cell vi... 37197457
Unchecked IC50 = 12530.0 nM 4.9 Cytotoxicity against human C3PV cells assessed as reduction in cell viability in... 37197457
Tyrosinase IC50 = 26000.0 nM 4.58 Inhibition of human tyrosinase 38823727
Unchecked IC50 = 35300.0 nM 4.45 Inhibition of alpha-glucosidase using para-nitrophenyl substrate 21053896
Aldo-keto reductase family 1 member B1 IC50 = 62000.0 nM 4.21 Inhibition human recombinant aldose reductase 1 by spectrophotometric analysis 20805028
No relevant target EC50 = 65800.0 nM 4.18 Antioxidant activity assessed as DPPH radical scavenging activity 26519930

Literature References

PubMed DOI Target Context # Activities
23391306 10.1021/jm3017865 D-amino-acid oxidase 13
23631755 10.1021/jm4002583 D-amino-acid oxidase 5
23306152 10.3390/ijms14011293 Aspergillus fumigatus 5
21053896 10.1021/jm100757r Unchecked 4
23306152 10.3390/ijms14011293 Aspergillus flavus 4
18060791 10.1016/j.bmc.2007.11.038 U-937 3
20805028 10.1016/j.bmcl.2010.08.038 Unchecked 3
25408840 10.1021/ml500335z ADMET 2
37197457 10.1021/acsmedchemlett.3c00019 Unchecked 2
23391306 10.1021/jm3017865 D-aspartate oxidase 2
23391306 10.1021/jm3017865 Serine racemase 2
23391306 10.1021/jm3017865 Unchecked 2
23391306 10.1021/jm3017865 HEK293 2
25205194 10.1016/j.bmcl.2014.08.038 NON-PROTEIN TARGET 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
20805028 10.1016/j.bmcl.2010.08.038 Sorbitol dehydrogenase 1
37487307 10.1016/j.ejmech.2023.115672 Tyrosinase 1
20580555 10.1016/j.bmcl.2010.06.040 Carbonic anhydrase 12 1
20580555 10.1016/j.bmcl.2010.06.040 Carbonic anhydrase 1 1
20580555 10.1016/j.bmcl.2010.06.040 Carbonic anhydrase 2 1

Data from ChEMBL 36 via Core Engine