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Compound Detail

CHEMBL6466

COUMARIN
💊 Approved Drug
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💊 Approved Drug
O=c1ccc2ccccc2o1

Basic Information

ChEMBL ID CHEMBL6466
Name COUMARIN
Phase Approved
Structure Type MOL
InChI Key ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

1,2-benzopyrone Cis-o-coumarinic acid lactone Coumarin Coumarin (prohibited) Coumarinic lactone Coumarinum Cumarin Lodema Nci-c07103 NSC-8774 O-hydroxycinnamic acid lactone Tonka bean camphor
18
Targets
44
Activities
4
Assay Types
5
PK Parameters
20
Publications
12
Known Names
1
Mechanisms

Molecular Properties

146.1
MW (Da)
1.79
ALogP
2
HBA
0
HBD
30.2
PSA (Ų)
0.53
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C9H6O2
MW 146.14
Aromatic Rings 2
Heavy Atoms 11
NP-Likeness 0.23

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - -

Drug Warnings

Withdrawn
hepatotoxicity
Hepatic adverse effects
Country: France   Year: 1996
Withdrawn
hepatotoxicity
Hepatic adverse effects
Country: France   Year: 1996

Activity Summary

Ki 30 meas. best 7.32
IC50 11 meas. best 4.92
Kd 2 meas. best 6.64
EC50 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 14
CHEMBL3510
Ki 7.32 7.32 48.0 1
Sclerostin
CHEMBL3580487
Kd 6.64 6.6 230.8 2
Carbonic anhydrase 6
CHEMBL3025
Ki 5.7 5.7 2000.0 1
Carbonic anhydrase 1
CHEMBL261
Ki 5.51 5.51 3100.0 9
Carbonic anhydrase 7
CHEMBL2326
Ki 5.48 5.48 3300.0 1
Induced myeloid leukemia cell differentiation protein Mcl-1
CHEMBL4361
Ki 5.39 5.39 4060.0 1
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
Ki 5.28 5.28 5200.0 1
Carbonic anhydrase 3
CHEMBL2885
Ki 5.25 5.25 5600.0 1
Carbonic anhydrase 4
CHEMBL3729
Ki 5.17 4.69 6800.0 2
Carbonic anhydrase 12
CHEMBL3242
Ki 5.05 5.05 8900.0 1
Carbonic anhydrase 13
CHEMBL2186
Ki 5.04 5.04 9200.0 1
Carbonic anhydrase 9
CHEMBL3594
Ki 5.04 5.04 9100.0 1
Carbonic anhydrase 2
CHEMBL205
Ki 5.04 5.04 9200.0 8
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
Ki 5.03 5.03 9400.0 1
Amine oxidase [flavin-containing] B
CHEMBL2993
IC50 4.92 4.92 12022.6 1
Induced myeloid leukemia cell differentiation protein Mcl-1
CHEMBL4361
IC50 4.61 4.61 24380.0 1
Unchecked
CHEMBL612545
IC50 4.41 4.41 38620.0 1
Carbonic anhydrase 15
CHEMBL5973
Ki 4.4 4.4 39600.0 1
Amine oxidase [flavin-containing] A
CHEMBL3358
IC50 4.39 4.39 40738.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 17.0 mL.min-1.kg-1 Homo sapiens
CL 20.0 mL.min-1.kg-1 Rattus norvegicus
CL 22.0 mL.min-1.kg-1 Canis lupus familiaris
CL 34.0 mL.min-1.kg-1 Macaca
F 20.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 14 Ki = 48.0 nM 7.32 Inhibition of human carbonic anhydrase 14 by stopped flow CO2 hydration assay 19911821
Sclerostin Kd = 230.8 nM 6.64 Binding affinity to SOST loop2 (unknown origin) by SPR analysis 38677061
Sclerostin Kd = 273.3 nM 6.56 Binding affinity to SOST (unknown origin) by SPR analysis 38677061
Carbonic anhydrase 6 Ki = 2000.0 nM 5.7 Inhibition of human carbonic anhydrase 6 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 1 Ki = 3100.0 nM 5.51 Inhibition of human carbonic anhydrase 1 by Stopped-Flow CO2 Hydrase assay 26688270
Carbonic anhydrase 1 Ki = 3100.0 nM 5.51 Inhibition of human carbonic anhydrase 1 preincubated for 6 hrs by CO2 hydration... 22892213
Carbonic anhydrase 1 Ki = 3100.0 nM 5.51 Inhibition of full length human recombinant CA1 cytosolic isoform after 6 hrs by... 23241068
Carbonic anhydrase 1 Ki = 3100.0 nM 5.51 Inhibition of human carbonic anhydrase 1 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 1 Ki = 3100.0 nM 5.51 Inhibition of full length human CA1 cytosolic isoform by stopped-flow CO2 hydrat... 21067924
Carbonic anhydrase 1 Ki = 3100.0 nM 5.51 Inhibition of human CA1 pre-incubated for 15 mins to 24 hrs measured after 6 hrs... 22137345
Carbonic anhydrase 1 Ki = 3100.0 nM 5.51 Inhibition of human full-length cytosolic CA1 after 6 hrs by stopped flow CO2 hy... 22077347
Carbonic anhydrase 1 Ki = 3100.0 nM 5.51 Inhibition of human recombinant carbonic anhydrase 1 preincubated for 15 mins to... 22365761
Carbonic anhydrase 1 Ki = 3100.0 nM 5.51 Inhibition of human carbonic anhydrase 1 after 6 hrs by stop-flow CO2 hydration ... 22377674
Carbonic anhydrase 7 Ki = 3300.0 nM 5.48 Inhibition of human carbonic anhydrase 7 by stopped flow CO2 hydration assay 19911821
Induced myeloid leukemia cell differentiation protein Mcl-1 Ki = 4060.0 nM 5.39 Displacement of FAM-Bid peptide from recombinant N-terminal His6x-tagged human M... 33218896
Carbonic anhydrase 5B, mitochondrial Ki = 5200.0 nM 5.28 Inhibition of human carbonic anhydrase 5B by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 3 Ki = 5600.0 nM 5.25 Inhibition of human carbonic anhydrase 3 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 4 Ki = 6800.0 nM 5.17 Inhibition of human carbonic anhydrase 4 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 12 Ki = 8900.0 nM 5.05 Inhibition of human carbonic anhydrase 12 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 2 Ki = 9200.0 nM 5.04 Inhibition of human full-length cytosolic CA2 after 6 hrs by stopped flow CO2 hy... 22077347

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1423
- 10.6019/CHEMBL3885881 Rattus norvegicus 270
3069958 10.1021/np50060a016 Salmonella typhimurium 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15920768 10.1002/jps.20373 ADMET 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
14741253 10.1016/j.bmcl.2003.11.060 Unchecked 7
37725043 10.1021/acs.jmedchem.3c01254 Candida albicans 7
23306152 10.3390/ijms14011293 Aspergillus fumigatus 5
14741253 10.1016/j.bmcl.2003.11.060 Chymotrypsinogen B 4
23306152 10.3390/ijms14011293 Aspergillus flavus 4
19150597 10.1016/j.bmcl.2008.12.098 Radical scavenging activity 4
14741253 10.1016/j.bmcl.2003.11.060 Serine protease 1 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
20879794 10.1021/jf102525e No relevant target 4
16019946 10.1080/00498250400028197 ADMET 4
15115404 10.1021/jm030473r NAD-dependent histone deacetylase SIR2 3
22000208 10.1016/j.ejmech.2011.09.053 Radical scavenging activity 3
38677061 10.1016/j.ejmech.2024.116414 Sclerostin 3
32904099 10.1039/C9MD00358D No relevant target 3

Data from ChEMBL 36 via Core Engine