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Compound Detail

CHEMBL75897

2'-HYDROXY-FLAVANONE
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O=C1CC(c2ccccc2O)Oc2ccccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL75897
Name 2'-HYDROXY-FLAVANONE
Phase Preclinical
Structure Type MOL
InChI Key KZKWCKFDCPVDFJ-UHFFFAOYSA-N
12
Targets
18
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

240.3
MW (Da)
3.10
ALogP
3
HBA
1
HBD
46.5
PSA (Ų)
0.83
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 C15H12O3
MW 240.26
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness 1.17

Activity Summary

IC50 15 meas. best 7.0
Ki 3 meas. best 5.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aldo-keto reductase family 1 member C3
CHEMBL4681
 IC50 7.0 6.68 100.0 3
Acetylcholinesterase
CHEMBL3199
 IC50 6.83 6.83 149.0 1
PC-3
CHEMBL390
 IC50 5.59 5.59 2560.0 1
Adenosine receptor A1
CHEMBL318
 Ki 5.58 5.58 2640.0 1
DU-145
CHEMBL613508
 IC50 5.39 5.39 4110.0 1
LNCaP
CHEMBL612518
 IC50 5.26 5.26 5450.0 1
Adenosine receptor A3
CHEMBL256
 Ki 5.22 5.22 6070.0 1
Androgen receptor
CHEMBL1871
 IC50 5.19 5.19 6400.0 1
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL4235
 IC50 5.0 5.0 10000.0 1
Adenosine A2 receptor
CHEMBL2094117
 Ki 4.75 4.75 17600.0 1
RAW264.7
CHEMBL612557
 IC50 4.15 4.15 71300.0 3
J774.A1
CHEMBL614040
 IC50 4.15 4.15 71300.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aldo-keto reductase family 1 member C3 IC50 = 100.0 nM 7.0 Inhibition of AKR1C3 22877157
Acetylcholinesterase IC50 = 149.0 nM 6.83 Inhibition of AchE in Rattus norvegicus (rat) cortex homogenates by Ellman's met... -
Aldo-keto reductase family 1 member C3 IC50 = 300.0 nM 6.52 Inhibition of recombinant human AKR1C3 expressed in Escherichia coli BL21 (D3) u... 30836001
Aldo-keto reductase family 1 member C3 IC50 = 300.0 nM 6.52 Inhibition of human recombinant His-tagged AKR1C3 expressed in Escherichia coli ... 33444847
PC-3 IC50 = 2560.0 nM 5.59 Antiproliferative activity against human PC3 cells assessed as reduction in cell... 30189396
Adenosine receptor A1 Ki = 2640.0 nM 5.58 Binding affinity at Adenosine A1 receptor in rat brain membranes by [3H]PIA disp... 8691424
DU-145 IC50 = 4110.0 nM 5.39 Antiproliferative activity against human DU145 cells assessed as reduction in ce... 30189396
LNCaP IC50 = 5450.0 nM 5.26 Antiproliferative activity against human LNCAP cells assessed as reduction in ce... 30189396
Adenosine receptor A3 Ki = 6070.0 nM 5.22 Binding affinity against human adenosine A3 receptor in HEK293 cells using [125I... 8691424
Androgen receptor IC50 = 6400.0 nM 5.19 Antagonist activity at AR in human LNCAP cells assessed as reduction in DHT-indu... 30189396
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 10000.0 nM 5.0 Inhibition of human 11beta-HSD1 expressed in HEK-293 cells incubated for 10 mins 33444847
Adenosine A2 receptor Ki = 17600.0 nM 4.75 Binding affinity at Adenosine A2 receptor in rat striatal membranes by [3H]-CGS-... 8691424
J774.A1 IC50 = 71300.0 nM 4.15 Inhibition of TNFalpha production in mouse J774A.1 cells incubated for 6 hrs by ... 25824662
RAW264.7 IC50 = 71300.0 nM 4.15 Inhibition of IL-1beta production in mouse RAW264.7 cells incubated for 12 hrs b... 25824662
J774.A1 IC50 = 71300.0 nM 4.15 Inhibition of IL-1beta production in mouse J774A.1 cells incubated for 12 hrs by... 25824662
RAW264.7 IC50 = 71300.0 nM 4.15 Inhibition of TNFalpha production in mouse RAW264.7 cells incubated for 6 hrs by... 25824662
J774.A1 IC50 = 71300.0 nM 4.15 Inhibition of LPS-induced nitric oxide production in mouse J774A.1 cells pre-inc... 25824662
RAW264.7 IC50 = 71300.0 nM 4.15 Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells pre-in... 25824662

Literature References

PubMed DOI Target Context # Activities
30189396 10.1016/j.ejmech.2018.08.069 Androgen receptor 5
25824662 10.1016/j.bmcl.2015.03.025 J774.A1 3
25824662 10.1016/j.bmcl.2015.03.025 RAW264.7 3
17166721 10.1016/j.bmc.2006.11.037 NON-PROTEIN TARGET 3
18533708 10.1021/jm800054h 17-beta-hydroxysteroid dehydrogenase type 2 2
30189396 10.1016/j.ejmech.2018.08.069 LNCaP 2
19236029 10.1021/np800698d Enterococcus faecalis 2
18533708 10.1021/jm800054h 17-beta-hydroxysteroid dehydrogenase type 1 2
17166721 10.1016/j.bmc.2006.11.037 Radical scavenging activity 1
8691424 10.1021/jm950923i Adenosine receptors; A1 & A3 1
9438021 10.1021/jm970446z Adenosine receptor A1 1
19307119 10.1016/j.bmcl.2009.03.017 HEK293 1
19307119 10.1016/j.bmcl.2009.03.017 HeLa 1
19236029 10.1021/np800698d Unchecked 1
8691424 10.1021/jm950923i Adenosine receptor A3 1
19944611 10.1016/j.bmc.2009.11.015 No relevant target 1
33444847 10.1016/j.bmc.2021.116001 No relevant target 1
8691424 10.1021/jm950923i Adenosine A2 receptor 1
8691424 10.1021/jm950923i Adenosine receptor A1 1
9438021 10.1021/jm970446z Adenosine receptor A3 1

Data from ChEMBL 36 via Core Engine