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Compound Detail

CHEMBL75267

7,8-DIHYDROXYFLAVONE
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O=c1cc(-c2ccccc2)oc2c(O)c(O)ccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL75267
Name 7,8-DIHYDROXYFLAVONE
Phase Preclinical
Structure Type MOL
InChI Key COCYGNDCWFKTMF-UHFFFAOYSA-N
13
Targets
15
Activities
3
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

254.2
MW (Da)
2.87
ALogP
4
HBA
2
HBD
70.7
PSA (Ų)
0.65
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 3
Heavy Atoms 19
NP-Likeness 0.97

Activity Summary

IC50 11 meas. best 5.01
EC50 2 meas. best 6.57
Kd 2 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
BDNF/NT-3 growth factors receptor
CHEMBL4898
 Kd 8.0 7.25 10.0 2
Trypanosoma brucei rhodesiense
CHEMBL612348
 EC50 6.57 6.57 270.0 1
Inhibitor of nuclear factor kappa-B kinase subunit beta
CHEMBL1991
 IC50 5.01 5.01 9820.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 5.0 5.0 10000.0 1
Arginase
CHEMBL3108635
 IC50 4.92 4.92 12000.0 1
H9
CHEMBL614806
 IC50 4.85 4.85 14000.0 1
No relevant target
CHEMBL2362975
 IC50 4.81 4.81 15500.0 1
Monoamine oxidase
CHEMBL2095205
 IC50 4.77 4.77 17000.0 1
MCF7
CHEMBL387
 IC50 4.56 4.56 27500.0 1
Telomerase reverse transcriptase
CHEMBL2916
 IC50 4.44 4.44 36000.0 2
A549
CHEMBL392
 IC50 4.43 4.43 37250.0 1
U-251
CHEMBL615022
 IC50 4.3 4.3 50110.0 1
Aromatase
CHEMBL1978
 IC50 4.08 4.08 82985.1 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 111.0 nM hr ml -
Tmax 0.5 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
BDNF/NT-3 growth factors receptor Kd = 10.0 nM 8.0 Binding affinity to recombinant human TrkB receptor ECD assessed as dissociation... 35489224
Trypanosoma brucei rhodesiense EC50 = 270.0 nM 6.57 Antitrypanosomal activity against bloodstream form of Trypanosoma brucei rhodesi... 30234295
BDNF/NT-3 growth factors receptor Kd = 320.0 nM 6.5 Binding affinity to TrkB receptor extracellular domain (unknown origin) after 10... 24183588
Inhibitor of nuclear factor kappa-B kinase subunit beta IC50 = 9820.0 nM 5.01 Inhibition of IKK-beta using TMB substrate after 15 mins by spectrophotometer an... 22472167
Human immunodeficiency virus 1 EC50 = 10000.0 nM 5.0 Antiviral activity against HIV1 3B infected in human H9 cells assessed as inhibi... 8158164
Arginase IC50 = 12000.0 nM 4.92 Inhibition of Leishmania amazonensis Arginase 37257213
H9 IC50 = 14000.0 nM 4.85 Cytotoxicity against human H9 cells after 3 days 8158164
No relevant target IC50 = 15500.0 nM 4.81 Antioxidant activity assessed as DPPH free radical scavenging activity after 30 ... 27663547
Monoamine oxidase IC50 = 17000.0 nM 4.77 Inhibition of Hamster Liver mitochondrial Monoamine oxidase. 11063613
MCF7 IC50 = 27500.0 nM 4.56 The compound was tested for antiproliferative activity against MCF-7 human breas... 11720850
Telomerase reverse transcriptase IC50 = 36000.0 nM 4.44 Inhibition of human telomerase from HEK293 cell extracts by Flash-Plate assay 15588081
Telomerase reverse transcriptase IC50 = 36000.0 nM 4.44 Inhibition of telomerase extracted from HEK293 cells using 5'-bAATCCGTCGAGCAGAGT... -
A549 IC50 = 37250.0 nM 4.43 Antiproliferative activity against human A549 cells after 24 hrs by MTT assay 22472167
U-251 IC50 = 50110.0 nM 4.3 Antiproliferative activity against human U251 cells after 24 hrs by MTT assay 22472167
Aromatase IC50 = 82985.08 nM 4.08 Inhibition of human aromatase using ASD as substrate pre-incubated for 5 mins fo... 28622580

Literature References

PubMed DOI Target Context # Activities
21073191 10.1021/jm101206p Mus musculus 22
21073191 10.1021/jm101206p BDNF/NT-3 growth factors receptor 5
11063613 10.1021/jm990614i Monoamine oxidase 5
11063613 10.1021/jm990614i Aldehyde dehydrogenase, mitochondrial 4
- 10.1016/S0960-894X(01)80881-7 Escherichia coli 4
21073191 10.1021/jm101206p HEK293 3
27663547 10.1016/j.bmc.2016.09.006 No relevant target 3
27663547 10.1016/j.bmc.2016.09.006 NON-PROTEIN TARGET 3
33479614 10.1039/c9md00451c BDNF/NT-3 growth factors receptor 3
38355400 10.1021/acs.jnatprod.3c00172 SH-SY5Y 3
- 10.1016/S0960-894X(01)80881-7 Salmonella typhimurium 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.1016/S0960-894X(01)80881-7 Stenotrophomonas maltophilia 2
11063613 10.1021/jm990614i ADMET 2
- 10.1016/S0960-894X(01)80881-7 Staphylococcus epidermidis 1
- 10.1016/S0960-894X(01)80881-7 Staphylococcus aureus 1
- 10.1016/S0960-894X(01)80881-7 DNA topoisomerase 2-beta 1
11063613 10.1021/jm990614i Unchecked 1
8158164 10.1021/np50103a006 ADMET 1
37257213 10.1016/j.ejmech.2023.115471 Arginase 1

Data from ChEMBL 36 via Core Engine