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Compound Detail

CHEMBL426110

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O=C1/C(=C/c2ccc(O)cc2)Oc2cc(O)ccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL426110
Phase Preclinical
Structure Type MOL
InChI Key KEZLDSPIRVZOKZ-AUWJEWJLSA-N
8
Targets
14
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

254.2
MW (Da)
2.71
ALogP
4
HBA
2
HBD
66.8
PSA (Ų)
0.77
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 C15H10O4
MW 254.24
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness 0.36

Activity Summary

IC50 11 meas. best 6.58
Ki 3 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Amine oxidase [flavin-containing] A
CHEMBL1951
 Ki 7.0 7.0 100.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 6.58 5.93 260.0 2
Adenosine receptor A1
CHEMBL318
 Ki 6.45 6.45 352.0 1
HT-29
CHEMBL384
 IC50 6.3 6.3 500.0 1
Amine oxidase [flavin-containing] B
CHEMBL2039
 Ki 6.29 6.29 510.0 1
RAW264.7
CHEMBL612557
 IC50 5.97 4.7933 1060.0 3
Amine oxidase [flavin-containing] B
CHEMBL2039
 IC50 5.61 5.61 2450.0 1
Tyrosinase
CHEMBL1973
 IC50 4.42 4.42 38400.0 1
Tyrosinase
CHEMBL3318
 IC50 4.42 4.42 38400.0 1
Unchecked
CHEMBL612545
 IC50 4.12 4.12 76710.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Amine oxidase [flavin-containing] A Ki = 100.0 nM 7.0 Competitive inhibition of human recombinant MAOA using 0.006 to 0.15 mM kynurami... 29395970
Amine oxidase [flavin-containing] A IC50 = 260.0 nM 6.58 Inhibition of human recombinant MAOA using kynuramine as substrate preincubated ... 29395970
Adenosine receptor A1 Ki = 352.0 nM 6.45 Antagonist activity at rat adenosine A1 receptor 30881617
HT-29 IC50 = 500.0 nM 6.3 Inhibition of TNF-alpha-induced adhesion of BCECF-labeled human U937 cells to hu... 28646757
Amine oxidase [flavin-containing] B Ki = 510.0 nM 6.29 Competitive inhibition of human recombinant MAOB using 0.06 to 1.5 mM benzylamin... 29395970
RAW264.7 IC50 = 1060.0 nM 5.97 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 21723122
Amine oxidase [flavin-containing] B IC50 = 2450.0 nM 5.61 Inhibition of human recombinant MAOB using benzylamine as substrate preincubated... 29395970
Amine oxidase [flavin-containing] A IC50 = 5280.0 nM 5.28 Inhibition of human recombinant MAO-A using p-tyramine as substrate preincubated... 39004050
Tyrosinase IC50 = 38400.0 nM 4.42 Inhibitory activity against tyrosinase in human melanocytes 16392817
Tyrosinase IC50 = 38400.0 nM 4.42 Inhibition of mushroom tyrosinase 29763564
RAW264.7 IC50 = 38700.0 nM 4.41 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 21723122
Unchecked IC50 = 76710.0 nM 4.12 Inhibition of baker's yeast alpha-glucosidase incubated for 30 mins using p-nitr... 28651984
RAW264.7 IC50 = 99790.0 nM 4.0 Cytotoxicity against mouse RAW264.7 cells after 24 hrs by MTT assay 21723122

Literature References

PubMed DOI Target Context # Activities
28646757 10.1016/j.ejmech.2017.06.018 HT-29 12
29395970 10.1016/j.bmcl.2018.01.049 Amine oxidase [flavin-containing] A 5
29395970 10.1016/j.bmcl.2018.01.049 Amine oxidase [flavin-containing] B 4
21723122 10.1016/j.bmcl.2011.05.117 RAW264.7 3
28646757 10.1016/j.ejmech.2017.06.018 Rattus norvegicus 3
39004050 10.1016/j.bmc.2024.117826 Amine oxidase [flavin-containing] B 2
16392817 10.1021/jm050715i Tyrosinase 2
37487307 10.1016/j.ejmech.2023.115672 Mushroom tyrosinase 2
29763564 10.1021/acs.jmedchem.7b00967 Tyrosinase 2
21699179 10.1021/jm200242p Unchecked 2
20392544 10.1016/j.ejmech.2010.03.023 ADMET 2
20392544 10.1016/j.ejmech.2010.03.023 NAD(P)H dehydrogenase [quinone] 1 2
29925480 10.1016/j.bmcl.2018.06.023 Unchecked 1
28651984 10.1016/j.bmcl.2017.06.040 Unchecked 1
21699179 10.1021/jm200242p HEK293 1
21699179 10.1021/jm200242p Huh-7 1
29395970 10.1016/j.bmcl.2018.01.049 Unchecked 1
30665143 10.1016/j.ejmech.2019.01.022 Staphylococcus aureus 1
30665143 10.1016/j.ejmech.2019.01.022 Pseudomonas aeruginosa 1
20630767 10.1016/j.bmc.2010.06.008 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine