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Compound Detail

CHEMBL83294

COUMARIN-3-CARBOXYLIC ACID
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O=C(O)c1cc2ccccc2oc1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL83294
Name COUMARIN-3-CARBOXYLIC ACID
Phase Preclinical
Structure Type MOL
InChI Key ACMLKANOGIVEPB-UHFFFAOYSA-N
14
Targets
16
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

190.2
MW (Da)
1.49
ALogP
3
HBA
1
HBD
67.5
PSA (Ų)
0.69
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C10H6O4
MW 190.15
Aromatic Rings 2
Heavy Atoms 14
NP-Likeness -0.21

Activity Summary

Ki 12 meas. best 5.54
IC50 3 meas. best 7.76
EC50 1 meas. best 4.04

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Amine oxidase [flavin-containing] B
CHEMBL2039
 IC50 7.76 7.76 17.4 1
Carbonic anhydrase 12
CHEMBL3242
 Ki 5.54 5.54 2900.0 1
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 Ki 5.35 5.35 4500.0 1
Carbonic anhydrase 7
CHEMBL2326
 Ki 5.21 5.21 6200.0 1
Carbonic anhydrase 9
CHEMBL3594
 Ki 5.19 5.19 6500.0 1
Carbonic anhydrase 3
CHEMBL2885
 Ki 5.18 5.18 6600.0 1
Carbonic anhydrase 14
CHEMBL3510
 Ki 5.09 5.09 8200.0 1
Carbonic anhydrase 15
CHEMBL5973
 Ki 5.06 5.06 8800.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 5.03 5.03 9300.0 1
Carbonic anhydrase 4
CHEMBL3729
 Ki 5.01 5.01 9700.0 1
Carbonic anhydrase 13
CHEMBL2186
 Ki 4.69 4.69 20300.0 1
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
 Ki 4.46 4.46 34300.0 1
Carbonic anhydrase 6
CHEMBL3025
 Ki 4.12 4.12 76300.0 1
G-protein coupled receptor 35
CHEMBL1293267
 EC50 4.04 4.04 92260.0 1
G-protein coupled receptor 35
CHEMBL1293267
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Amine oxidase [flavin-containing] B IC50 = 17.38 nM 7.76 Inhibition of MAO-B (unknown origin) 23517722
Carbonic anhydrase 12 Ki = 2900.0 nM 5.54 Inhibition of human carbonic anhydrase 12 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 5A, mitochondrial Ki = 4500.0 nM 5.35 Inhibition of human carbonic anhydrase 5A by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 7 Ki = 6200.0 nM 5.21 Inhibition of human carbonic anhydrase 7 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 9 Ki = 6500.0 nM 5.19 Inhibition of human carbonic anhydrase 9 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 3 Ki = 6600.0 nM 5.18 Inhibition of human carbonic anhydrase 3 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 14 Ki = 8200.0 nM 5.09 Inhibition of human carbonic anhydrase 14 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 15 Ki = 8800.0 nM 5.06 Inhibition of mouse carbonic anhydrase 15 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 1 Ki = 9300.0 nM 5.03 Inhibition of human carbonic anhydrase 1 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 4 Ki = 9700.0 nM 5.01 Inhibition of human carbonic anhydrase 4 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 13 Ki = 20300.0 nM 4.69 Inhibition of mouse carbonic anhydrase 13 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 5B, mitochondrial Ki = 34300.0 nM 4.46 Inhibition of human carbonic anhydrase 5B by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 6 Ki = 76300.0 nM 4.12 Inhibition of human carbonic anhydrase 6 by stopped flow CO2 hydration assay 19911821
G-protein coupled receptor 35 EC50 = 92260.0 nM 4.04 Agonist activity at GPR35 in human HT-29 cells by DMR assay 27976894
G-protein coupled receptor 35 IC50 = 100000.0 nM 4.0 Agonist activity at GPR35 in human HT-29 cells assessed as induction of cell des... 27976894

Literature References

PubMed DOI Target Context # Activities
23306152 10.3390/ijms14011293 Aspergillus fumigatus 5
25011038 10.1016/j.ejmech.2014.07.009 No relevant target 4
23306152 10.3390/ijms14011293 Aspergillus flavus 4
27976894 10.1021/acs.jmedchem.6b01431 G-protein coupled receptor 35 3
23682762 10.1021/jm400374q Unchecked 2
23220643 10.1016/j.ejmech.2012.11.019 Staphylococcus aureus 2
19911821 10.1021/jm901287j Carbonic anhydrase 4 1
23321562 10.1016/j.bmcl.2012.12.051 Bacillus subtilis 1
23220643 10.1016/j.ejmech.2012.11.019 Klebsiella pneumoniae 1
19911821 10.1021/jm901287j Carbonic anhydrase 2 1
19911821 10.1021/jm901287j Carbonic anhydrase 3 1
33956447 10.1021/acs.jnatprod.1c00128 HepG2 1
19911821 10.1021/jm901287j Carbonic anhydrase 5A, mitochondrial 1
19911821 10.1021/jm901287j Carbonic anhydrase 5B, mitochondrial 1
19911821 10.1021/jm901287j Carbonic anhydrase 6 1
19911821 10.1021/jm901287j Carbonic anhydrase 7 1
19911821 10.1021/jm901287j Carbonic anhydrase 9 1
19911821 10.1021/jm901287j Carbonic anhydrase 15 1
19911821 10.1021/jm901287j Carbonic anhydrase 14 1
19911821 10.1021/jm901287j Carbonic anhydrase 13 1

Data from ChEMBL 36 via Core Engine