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Compound Detail

CHEMBL52564

O-COUMARIC ACID
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O=C(O)/C=C/c1ccccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL52564
Name O-COUMARIC ACID
Phase Preclinical
Structure Type MOL
InChI Key PMOWTIHVNWZYFI-AATRIKPKSA-N
7
Targets
19
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

164.2
MW (Da)
1.49
ALogP
2
HBA
2
HBD
57.5
PSA (Ų)
0.65
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C9H8O3
MW 164.16
Aromatic Rings 1
Heavy Atoms 12
NP-Likeness 0.58

Activity Summary

IC50 10 meas. best 6.72
Ki 8 meas. best 5.51
EC50 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mus musculus
CHEMBL375
 IC50 6.72 6.72 190.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 5.51 5.4967 3100.0 3
Carbonic anhydrase 2
CHEMBL205
 Ki 5.04 5.0367 9200.0 3
Leishmania amazonensis
CHEMBL612877
 IC50 4.86 4.86 13800.0 1
Leishmania donovani
CHEMBL367
 IC50 4.44 4.44 36550.0 1
Nuclear factor NF-kappa-B p105 subunit
CHEMBL3251
 IC50 4.3 4.3 50000.0 1
Carbonic anhydrase 4
CHEMBL3729
 Ki 4.21 4.21 62300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mus musculus IC50 = 190.0 nM 6.72 Antihemorrhagic activity in ddY mouse assessed as inhibition of Protobothrops fl... 21388814
Carbonic anhydrase 1 Ki = 3100.0 nM 5.51 Inhibition of human carbonic anhydrase 1 after 15 mins by stopped flow CO2 hydra... 20674354
Carbonic anhydrase 1 Ki = 3100.0 nM 5.51 Inhibition of human carbonic anhydrase 1 preincubated for 15 mins by CO2 hydrati... 21282059
Carbonic anhydrase 1 Ki = 3400.0 nM 5.47 Inhibition of human CA1 pre-incubated for 15 mins to 24 hrs measured after 6 hrs... 22137345
Carbonic anhydrase 2 Ki = 9200.0 nM 5.04 Inhibition of human carbonic anhydrase 2 after 15 mins by stopped flow CO2 hydra... 20674354
Carbonic anhydrase 2 Ki = 9200.0 nM 5.04 Inhibition of human carbonic anhydrase 2 preincubated for 15 mins by CO2 hydrati... 21282059
Carbonic anhydrase 2 Ki = 9300.0 nM 5.03 Inhibition of human CA2 pre-incubated for 15 mins to 24 hrs measured after 6 hrs... 22137345
Leishmania amazonensis IC50 = 13800.0 nM 4.86 Antileishmanial activity against Leishmania amazonensis MHOM/77BR/LTB0016 amasti... 30145372
Leishmania donovani IC50 = 36550.0 nM 4.44 Antileishmanial activity against Leishmania donovani MHOM/ET/67/L82 amastigotes ... 30145372
Nuclear factor NF-kappa-B p105 subunit IC50 = 50000.0 nM 4.3 Inhibition of NF-KB p50 subunit/DNA interaction after 20 mins by EMSA 20980154
Carbonic anhydrase 4 Ki = 62300.0 nM 4.21 Inhibition of human carbonic anhydrase 4 after 15 mins by stopped flow CO2 hydra... 20674354

Literature References

PubMed DOI Target Context # Activities
18590964 10.1016/j.bmc.2008.06.010 Radical scavenging activity 6
- 10.1039/C4MD00022F NON-PROTEIN TARGET 5
22677314 10.1016/j.bmcl.2012.05.051 Xanthine dehydrogenase/oxidase 2
- 10.1584/jpestics.G10-84 Ralstonia solanacearum 2
15780639 10.1016/j.bmcl.2005.01.070 Mus musculus 2
30145372 10.1016/j.ejmech.2018.08.033 Dihydroorotate dehydrogenase (fumarate) 2
28415050 10.1016/j.ejmech.2017.03.061 No relevant target 2
20674354 10.1016/j.bmcl.2010.07.038 Carbonic anhydrase 3 1
20674354 10.1016/j.bmcl.2010.07.038 Carbonic anhydrase 13 1
20674354 10.1016/j.bmcl.2010.07.038 Carbonic anhydrase 12 1
20674354 10.1016/j.bmcl.2010.07.038 Carbonic anhydrase 7 1
20674354 10.1016/j.bmcl.2010.07.038 Carbonic anhydrase 6 1
20674354 10.1016/j.bmcl.2010.07.038 Carbonic anhydrase 5B, mitochondrial 1
20674354 10.1016/j.bmcl.2010.07.038 Carbonic anhydrase 5A, mitochondrial 1
20674354 10.1016/j.bmcl.2010.07.038 Carbonic anhydrase 4 1
20674354 10.1016/j.bmcl.2010.07.038 Carbonic anhydrase 1 1
19555125 10.1021/np900031q Tyrosinase 1
27411733 10.1021/acs.jmedchem.6b00698 Trypanosoma brucei brucei 1
15125954 10.1016/j.bmcl.2004.03.037 Unchecked 1
12951092 10.1016/s0960-894x(03)00710-8 RBL-2H3 1

Data from ChEMBL 36 via Core Engine