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Compound Detail

CHEMBL394855

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O=C(/C=C/c1ccc(O)cc1O)c1ccc(O)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL394855
Phase Preclinical
Structure Type MOL
InChI Key ZWTDXYUDJYDHJR-QHHAFSJGSA-N
6
Targets
9
Activities
1
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

272.3
MW (Da)
2.41
ALogP
5
HBA
4
HBD
98.0
PSA (Ų)
0.51
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 C15H12O5
MW 272.26
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.67

Activity Summary

IC50 9 meas. best 7.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mushroom tyrosinase
CHEMBL6066154
 IC50 7.22 7.22 60.0 1
Tyrosinase
CHEMBL1973
 IC50 7.16 7.16 70.0 1
Aldo-keto reductase family 1 member B1
CHEMBL2622
 IC50 6.8 6.8 160.0 1
Unchecked
CHEMBL612545
 IC50 5.54 5.32 2900.0 3
Tyrosinase
CHEMBL3318
 IC50 5.3 5.3 5000.0 2
Tyrosinase
CHEMBL5346
 IC50 5.3 5.3 5000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mushroom tyrosinase IC50 = 60.0 nM 7.22 Inhibition of monophenolase activity of mushroom tyrosinase using L-Tyrosine sub... 27720556
Tyrosinase IC50 = 70.0 nM 7.16 Inhibition of tyrosinase (unknown origin) 29763564
Aldo-keto reductase family 1 member B1 IC50 = 160.0 nM 6.8 Inhibition of Rattus norvegicus (rat) lens aldose reductase -
Unchecked IC50 = 2900.0 nM 5.54 Inhibition of PMA-induce ROS/RNS generation in human neutrophils measured up to ... 33006891
Unchecked IC50 = 3000.0 nM 5.52 Inhibition of PMA-induce ROS/RNS generation in human neutrophils measured up to ... 33006891
Tyrosinase IC50 = 5000.0 nM 5.3 Inhibition of mushroom tyrosinase 17267225
Tyrosinase IC50 = 5000.0 nM 5.3 Inhibition of mushroom tyrosinase assessed as reduction in diphenolase activity ... 23391365
Tyrosinase IC50 = 5000.0 nM 5.3 Inhibition of tyrosinase in mouse B16 cells assessed as reduction in melanin syn... 29763564
Unchecked IC50 = 12500.0 nM 4.9 Inhibition of alpha-glucosidase (unknown origin) using PNP glycoside as substrat... 28242551

Literature References

PubMed DOI Target Context # Activities
23391365 10.1016/j.bmc.2012.12.054 Tyrosinase 2
29763564 10.1021/acs.jmedchem.7b00967 Tyrosinase 2
33006891 10.1021/acs.jnatprod.0c00728 Unchecked 2
17267225 10.1016/j.bmc.2007.01.017 Tyrosinase 1
11678652 10.1021/np010288l Aromatase 1
- 10.1007/s00044-012-0367-5 Aldo-keto reductase family 1 member B1 1
28242551 10.1016/j.ejmech.2017.02.007 Unchecked 1
31255927 10.1016/j.ejmech.2019.06.034 RAW264.7 1
33006891 10.1021/acs.jnatprod.0c00728 Neutrophil 1
27720556 10.1016/j.bmc.2016.09.054 Mushroom tyrosinase 1
37683361 10.1016/j.ejmech.2023.115791 RAW264.7 1

Data from ChEMBL 36 via Core Engine