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Compound Detail

CHEMBL16807

5-HYDROXYFLAVONE
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O=c1cc(-c2ccccc2)oc2cccc(O)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL16807
Name 5-HYDROXYFLAVONE
Phase Preclinical
Structure Type MOL
InChI Key IYBLVRRCNVHZQJ-UHFFFAOYSA-N
11
Targets
14
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

238.2
MW (Da)
3.17
ALogP
3
HBA
1
HBD
50.4
PSA (Ų)
0.71
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 C15H10O3
MW 238.24
Aromatic Rings 3
Heavy Atoms 18
NP-Likeness 0.90

Activity Summary

IC50 10 meas. best 6.68
Ki 4 meas. best 5.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 1B1
CHEMBL4878
 IC50 6.68 6.68 210.0 1
Androgen receptor
CHEMBL1871
 IC50 6.52 6.2267 300.0 3
Cytochrome P450 1A2
CHEMBL3356
 IC50 6.51 6.51 310.0 1
Unchecked
CHEMBL612545
 IC50 6.37 6.37 425.0 1
Pyruvate kinase PKM
CHEMBL1075189
 IC50 5.86 5.86 1390.0 1
GABA-A receptor; anion channel
CHEMBL1907607
 Ki 5.72 5.72 1900.0 1
Adenosine receptor A1
CHEMBL318
 Ki 5.66 5.66 2170.0 1
Pyruvate kinase PKM
CHEMBL1075189
 Ki 5.45 5.45 3530.0 1
Cytochrome P450 1A1
CHEMBL2231
 IC50 5.39 5.39 4030.0 1
Adenosine receptor A2a
CHEMBL302
 Ki 5.21 5.21 6200.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.18 4.18 65900.0 1
Neutrophil
CHEMBL613710
 IC50 4.02 4.02 96000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 1B1 IC50 = 210.0 nM 6.68 Inhibition of human CYP1B1 expressed in Escherichia coli DH5alpha coexpressing h... 28458135
Androgen receptor IC50 = 300.0 nM 6.52 Antagonist activity at androgen receptor in human MDA-kb2 cells assessed as inhi... 19592245
Cytochrome P450 1A2 IC50 = 310.0 nM 6.51 Inhibition of CYP1A2 (unknown origin)-mediated demethylation of resorufin methyl... 23600958
Unchecked IC50 = 425.0 nM 6.37 Inhibition of beef heart mitochondrial NADH oxidase assessed per mg of protein 2959755
Androgen receptor IC50 = 831.76 nM 6.08 Antagonist activity at human androgen receptor LBD expressed in human MDA-kb2 ce... 23611768
Androgen receptor IC50 = 840.0 nM 6.08 Antagonist activity at human androgen receptor LBD expressed in human MDA-kb2 ce... 23611768
Pyruvate kinase PKM IC50 = 1390.0 nM 5.86 Inhibition of recombinant PKM2 (unknown origin) Thr129, Ser205, Hie78, Lys367, A... 34726055
GABA-A receptor; anion channel Ki = 1900.0 nM 5.72 In vitro affinity against Benzodiazepine receptor binding to rat cortical membra... 10543878
Adenosine receptor A1 Ki = 2170.0 nM 5.66 Displacement of specific [3H]PIA binding from adenosine A1 receptor in rat brain... 8576921
Pyruvate kinase PKM Ki = 3530.0 nM 5.45 Binding affinity to PKM2 (unknown origin) assessed as oxidation of beta-NADH by ... 34726055
Cytochrome P450 1A1 IC50 = 4030.0 nM 5.39 Inhibition of CYP1A1 (unknown origin)-mediated deethylation of resorufin ethyl e... 23600958
Adenosine receptor A2a Ki = 6200.0 nM 5.21 Affinity at Adenosine A2A receptor in rat striatal membranes by [3H]- CGS 21680 ... 8576921
Plasmodium falciparum IC50 = 65900.0 nM 4.18 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum NF54 16722653
Neutrophil IC50 = 96000.0 nM 4.02 Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as in... 23871908

Literature References

PubMed DOI Target Context # Activities
24793879 10.1016/j.ejmech.2014.04.054 Lipid bilayer 11
17624791 10.1016/j.bmc.2007.06.046 Unchecked 7
23871908 10.1016/j.ejmech.2013.06.019 Neutrophil 4
2959755 10.1021/np50051a014 Unchecked 4
24793879 10.1016/j.ejmech.2014.04.054 Unchecked 3
7769390 10.1021/np50116a009 DNA topoisomerase 2-alpha 2
19592245 10.1016/j.bmcl.2009.06.073 Glucocorticoid receptor 2
19592245 10.1016/j.bmcl.2009.06.073 Androgen receptor 2
34726055 10.1021/acs.jmedchem.1c00981 Pyruvate kinase PKM 2
20097567 10.1016/j.bmc.2009.12.062 Unchecked 2
16722653 10.1021/jm0600545 Plasmodium falciparum 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
23611768 10.1016/j.bmc.2013.03.060 Androgen receptor 2
9438021 10.1021/jm970446z Adenosine receptor A2a 2
10543878 10.1021/jm991010h GABA-A receptor; anion channel 2
16722653 10.1021/jm0600545 Enoyl-acyl-carrier protein reductase 1
16722653 10.1021/jm0600545 Fatty acid synthase 1
8523407 10.1021/jm00025a011 Rattus norvegicus 1
8576921 10.1021/jm950661k Adenosine receptor A2a 1
9438021 10.1021/jm970446z Adenosine receptor A3 1

Data from ChEMBL 36 via Core Engine