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Compound Detail

CHEMBL276473

4'-HYDROXYCHALCONE
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O=C(/C=C/c1ccccc1)c1ccc(O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL276473
Name 4'-HYDROXYCHALCONE
Phase Preclinical
Structure Type MOL
InChI Key UAHGNXFYLAJDIN-IZZDOVSWSA-N
19
Targets
29
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

224.3
MW (Da)
3.29
ALogP
2
HBA
1
HBD
37.3
PSA (Ų)
0.64
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 C15H12O2
MW 224.26
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness 0.24

Activity Summary

IC50 25 meas. best 9.92
EC50 4 meas. best 4.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tissue factor
CHEMBL4081
 IC50 9.92 9.92 0.1 1
Amine oxidase [flavin-containing] B
CHEMBL2039
 IC50 6.74 6.74 182.0 1
Cytochrome P450 1B1
CHEMBL4878
 IC50 5.95 5.95 1130.0 1
P388
CHEMBL389
 IC50 5.51 5.51 3120.0 1
Monoamine oxidase
CHEMBL2095205
 IC50 5.35 5.35 4500.0 1
Homo sapiens
CHEMBL372
 IC50 5.21 4.9733 6130.0 3
Aldehyde dehydrogenase, mitochondrial
CHEMBL1935
 IC50 5.16 5.16 7000.0 1
Leishmania donovani
CHEMBL367
 IC50 4.8 4.8 16000.0 1
Unchecked
CHEMBL612545
 IC50 4.7 4.53 20000.0 3
HSP60/HSP10
CHEMBL4106131
 IC50 4.7 4.7 20000.0 1
HCT-116
CHEMBL394
 EC50 4.7 4.69 20000.0 2
GroEL/GroES
CHEMBL4106139
 IC50 4.68 4.465 21000.0 2
L1210
CHEMBL386
 IC50 4.63 4.63 23500.0 1
ADMET
CHEMBL612558
 IC50 4.55 4.55 28000.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.53 4.53 29600.0 2
HT-29
CHEMBL384
 EC50 4.52 4.52 30000.0 1
Aromatase
CHEMBL1978
 IC50 4.51 4.51 30619.6 1
DLD-1
CHEMBL614285
 EC50 4.47 4.47 34000.0 1
Androgen receptor
CHEMBL3072
 IC50 4.24 4.24 57544.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tissue factor IC50 = 0.12 nM 9.92 Inhibition of tissue factor in Homo sapiens (human) THP1-cells using factor 10a ... -
Amine oxidase [flavin-containing] B IC50 = 182.0 nM 6.74 Inhibition of recombinant human MAOB using benzylamine as substrate after 30 min... 26337020
Cytochrome P450 1B1 IC50 = 1130.0 nM 5.95 Inhibition of human recombinant CYP1B1 assessed as fluorescence of resorufin 37315474
P388 IC50 = 3120.0 nM 5.51 Inhibition of proliferation of murine P388 cells 9544201
Monoamine oxidase IC50 = 4500.0 nM 5.35 Inhibition of hamster liver mitochondrial monoamine oxidase MAO 11563931
Homo sapiens IC50 = 6130.0 nM 5.21 Inhibition of the production of Interleukin-1-beta from human peripheral blood m... 8496911
Aldehyde dehydrogenase, mitochondrial IC50 = 7000.0 nM 5.16 Inhibition of hamster liver aldehyde dehydrogenase ALDH-2 11563931
Homo sapiens IC50 = 13100.0 nM 4.88 Concentration required to inhibit 50% growth of human Molt 4/C8 T-lymphocyte cel... 9544201
Homo sapiens IC50 = 14700.0 nM 4.83 Concentration required to inhibit 50% growth of Human CEM T-lymphocytes cells 9544201
Leishmania donovani IC50 = 16000.0 nM 4.8 Tested in vitro for anti-leishmanial activity against Leishmania donovani 9822551
HCT-116 EC50 = 20000.0 nM 4.7 Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability... 36356534
HSP60/HSP10 IC50 = 20000.0 nM 4.7 Inhibition of human N-terminal octa-His-tagged HSP60 expressed in Escherichia co... 30852084
Unchecked IC50 = 20000.0 nM 4.7 Inhibition of Escherichia coli GroEL expressed in NEB-5-alpha Escherichia coli c... 36356534
HCT-116 EC50 = 21000.0 nM 4.68 Cytotoxicity against p53-/- human HCT-116 cells assessed as reduction in cell vi... 36356534
Unchecked IC50 = 21000.0 nM 4.68 Inhibition of human mitochondrial HSP60 expressed in Escherichia coli Rosetta 2 ... 36356534
GroEL/GroES IC50 = 21000.0 nM 4.68 Inhibition of Escherichia coli GroEL expressed in Escherichia coliDH5alpha/Esche... 30852084
L1210 IC50 = 23500.0 nM 4.63 Concentration required to inhibit 50% growth of L1210 leukemia cells 9544201
ADMET IC50 = 28000.0 nM 4.55 Inhibitory activity against phytohemagglutininin A-induced proliferation of huma... 9822551
Plasmodium falciparum IC50 = 29600.0 nM 4.53 Growth inhibition of chloroquine-resistant Plasmodium falciparum K1 by [3H]hypox... 12161120
Plasmodium falciparum IC50 = 29600.0 nM 4.53 Inhibition of [3H]hypoxanthine incorporation in Plasmodium falciparum K1 11728189

Literature References

PubMed DOI Target Context # Activities
36356534 10.1016/j.bmc.2022.117072 Unchecked 7
30852084 10.1016/j.bmcl.2019.02.028 Unchecked 5
30852084 10.1016/j.bmcl.2019.02.028 GroEL/GroES 4
27210436 10.1016/j.bmcl.2016.05.013 Candida albicans 3
28655421 10.1016/j.bmcl.2017.01.053 No relevant target 2
- 10.1007/s00044-012-0330-5 Tissue factor 2
36356534 10.1016/j.bmc.2022.117072 HCT-116 2
9544201 10.1021/jm970432t Homo sapiens 2
9544201 10.1021/jm970432t L1210 1
- 10.1007/s00044-013-0745-7 Cyclooxygenase 1
- 10.1007/s00044-010-9305-6 Culex quinquefasciatus 1
37315474 10.1016/j.ejmech.2023.115552 Cytochrome P450 1B1 1
11728189 10.1021/jm0101747 Plasmodium falciparum 1
9857096 10.1021/jm980424s Quinone oxidoreductase 1
8254620 10.1021/jm00076a019 Rattus norvegicus 1
8254620 10.1021/jm00076a019 Cyclooxygenase 1
11563931 10.1021/jm0101390 Monoamine oxidase 1
11563931 10.1021/jm0101390 Aldehyde dehydrogenase, mitochondrial 1
9822551 10.1021/jm980410m ADMET 1
9822551 10.1021/jm980410m Leishmania donovani 1

Data from ChEMBL 36 via Core Engine