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Compound Detail

CHEMBL145781

7-BENZYLOXYCOUMARIN
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O=c1ccc2ccc(OCc3ccccc3)cc2o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL145781
Name 7-BENZYLOXYCOUMARIN
Phase Preclinical
Structure Type MOL
InChI Key QDLFCBKKECTJSK-UHFFFAOYSA-N
20
Targets
23
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

252.3
MW (Da)
3.37
ALogP
3
HBA
0
HBD
39.4
PSA (Ų)
0.67
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C16H12O3
MW 252.27
Aromatic Rings 3
Heavy Atoms 19
NP-Likeness -0.04

Activity Summary

Ki 12 meas. best 6.35
IC50 11 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MDA-MB-231
CHEMBL400
 IC50 9.4 9.4 0.4 1
Amine oxidase [flavin-containing] B
CHEMBL2039
 IC50 8.77 8.5367 1.7 3
Amine oxidase [flavin-containing] B
CHEMBL2993
 IC50 7.26 7.26 55.0 2
Unchecked
CHEMBL612545
 IC50 6.4 6.4 400.0 1
Melatonin receptor type 1A
CHEMBL1945
 Ki 6.35 6.35 445.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 5.46 5.46 3490.0 1
Carbonic anhydrase 9
CHEMBL3594
 Ki 5.37 5.37 4300.0 1
Carbonic anhydrase 15
CHEMBL5973
 Ki 5.34 5.34 4600.0 1
BT-549
CHEMBL614072
 IC50 5.27 5.27 5400.0 1
Carbonic anhydrase 14
CHEMBL3510
 Ki 5.25 5.25 5600.0 1
Carbonic anhydrase 4
CHEMBL3729
 Ki 5.24 5.24 5800.0 1
Carbonic anhydrase 12
CHEMBL3242
 Ki 5.19 5.19 6500.0 1
Amine oxidase [flavin-containing] A
CHEMBL3358
 IC50 5.17 5.17 6760.8 1
MCF7
CHEMBL387
 IC50 5.15 5.15 7100.0 1
Carbonic anhydrase 13
CHEMBL2186
 Ki 5.14 5.14 7300.0 1
Carbonic anhydrase 3
CHEMBL2885
 Ki 5.09 5.09 8100.0 1
Carbonic anhydrase 7
CHEMBL2326
 Ki 4.82 4.82 15300.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 4.57 4.57 26900.0 1
Carbonic anhydrase 2
CHEMBL205
 Ki 4.3 4.3 50300.0 1
Carbonic anhydrase 6
CHEMBL3025
 Ki 4.03 4.03 93100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MDA-MB-231 IC50 = 0.4 nM 9.4 Antiproliferative activity against human MDA-MB-231 cells after 24 hrs by MTT as... 29144746
Amine oxidase [flavin-containing] B IC50 = 1.698 nM 8.77 Inhibition of human supersomes MAOB 17034132
Amine oxidase [flavin-containing] B IC50 = 3.8 nM 8.42 Inhibition of recombinant human MAO-B assessed as reduction in 4-hydroxyquinolon... 27744252
Amine oxidase [flavin-containing] B IC50 = 3.8 nM 8.42 Inhibition of human MAO-B expressed in baculovirus infected BTI-TN-5B1-4 insect ... 38436571
Amine oxidase [flavin-containing] B IC50 = 54.95 nM 7.26 Inhibitory effect on Monoamine oxidase B, SD on IC50 values < 10% 11123983
Amine oxidase [flavin-containing] B IC50 = 54.95 nM 7.26 Inhibition of rat brain MAOB 17034132
Unchecked IC50 = 400.0 nM 6.4 Antiproliferative activity against mouse mammary carcinoma cell after 24 hrs by ... 29144746
Melatonin receptor type 1A Ki = 445.0 nM 6.35 Displacement of 2-[125I]iodomelatonin from human MT1 receptor expressed in CHO c... 29144746
Amine oxidase [flavin-containing] A IC50 = 3490.0 nM 5.46 Inhibition of recombinant human MAO-A assessed as reduction in 4-hydroxyquinolon... 27744252
Carbonic anhydrase 9 Ki = 4300.0 nM 5.37 Inhibition of human carbonic anhydrase 9 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 15 Ki = 4600.0 nM 5.34 Inhibition of mouse carbonic anhydrase 15 by stopped flow CO2 hydration assay 19911821
BT-549 IC50 = 5400.0 nM 5.27 Antiproliferative activity against human BT549 cells after 24 hrs by MTT assay 29144746
Carbonic anhydrase 14 Ki = 5600.0 nM 5.25 Inhibition of human carbonic anhydrase 14 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 4 Ki = 5800.0 nM 5.24 Inhibition of human carbonic anhydrase 4 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 12 Ki = 6500.0 nM 5.19 Inhibition of human carbonic anhydrase 12 by stopped flow CO2 hydration assay 19911821
Amine oxidase [flavin-containing] A IC50 = 6760.83 nM 5.17 Inhibitory effect on monoamine oxidase A, SD on IC50 values < 10% 11123983
MCF7 IC50 = 7100.0 nM 5.15 Antiproliferative activity against human MCF7 cells after 24 hrs by MTT assay 29144746
Carbonic anhydrase 13 Ki = 7300.0 nM 5.14 Inhibition of mouse carbonic anhydrase 13 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 3 Ki = 8100.0 nM 5.09 Inhibition of human carbonic anhydrase 3 by stopped flow CO2 hydration assay 19911821
Carbonic anhydrase 7 Ki = 15300.0 nM 4.82 Inhibition of human carbonic anhydrase 7 by stopped flow CO2 hydration assay 19911821

Literature References

PubMed DOI Target Context # Activities
10543892 10.1021/np990048u Salmonella typhimurium 7
29144746 10.1021/acs.jnatprod.7b00853 MCF7 2
17034132 10.1021/jm060441e Amine oxidase [flavin-containing] B 2
- 10.1016/j.ibiod.2012.07.016 Coptotermes formosanus 2
21880488 10.1016/j.bmcl.2011.08.005 PANC-1 2
29144746 10.1021/acs.jnatprod.7b00853 Unchecked 2
29144746 10.1021/acs.jnatprod.7b00853 MDA-MB-231 2
29144746 10.1021/acs.jnatprod.7b00853 BT-549 2
28525281 10.1021/acs.jnatprod.7b00173 Aryl hydrocarbon receptor 2
19911821 10.1021/jm901287j Carbonic anhydrase 7 1
19911821 10.1021/jm901287j Carbonic anhydrase 2 1
19911821 10.1021/jm901287j Carbonic anhydrase 4 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 15 1
19911821 10.1021/jm901287j Carbonic anhydrase 14 1
38436571 10.1021/acs.jmedchem.4c00045 SH-SY5Y 1
19911821 10.1021/jm901287j Carbonic anhydrase 12 1
10543892 10.1021/np990048u NON-PROTEIN TARGET 1

Data from ChEMBL 36 via Core Engine