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Compound Detail

CHEMBL7747

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

Basic Information

ChEMBL ID CHEMBL7747
Name 4-HYDROXYCHALCONE
Phase Preclinical
Structure Type MOL
InChI Key PWWCDTYUYPOAIU-DHZHZOJOSA-N
15
Targets
25
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 0.27

Activity Summary

IC50 21 meas. best 5.4
EC50 4 meas. best 4.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Leishmania major
CHEMBL612879
 IC50 5.4 5.4 4000.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.29 5.29 5095.0 1
Homo sapiens
CHEMBL372
 IC50 5.07 5.05 8580.0 2
Unchecked
CHEMBL612545
 IC50 5.06 4.758 8800.0 5
SGC-7901
CHEMBL614909
 IC50 4.86 4.86 13740.0 1
P388
CHEMBL389
 IC50 4.84 4.84 14300.0 1
GroEL/GroES
CHEMBL4106139
 IC50 4.68 4.54 21000.0 2
HSP60/HSP10
CHEMBL4106131
 IC50 4.66 4.66 22000.0 1
Nuclear factor NF-kappa-B complex
CHEMBL2094258
 IC50 4.62 4.62 24000.0 1
HT-29
CHEMBL384
 IC50 4.61 4.61 24600.0 1
A549
CHEMBL392
 IC50 4.58 4.58 26600.0 1
HCT-116
CHEMBL394
 EC50 4.5 4.5 32000.0 2
L1210
CHEMBL386
 IC50 4.42 4.42 37900.0 1
HT-29
CHEMBL384
 EC50 4.41 4.41 39000.0 1
Androgen receptor
CHEMBL3072
 IC50 4.32 4.32 47863.0 1
DLD-1
CHEMBL614285
 EC50 4.29 4.29 51000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Leishmania major IC50 = 4000.0 nM 5.4 Anti-leishmanial activity against Leishmania major 26188621
Cytochrome P450 3A4 IC50 = 5095.0 nM 5.29 Inhibition of CYP3A4 in human liver microsomes 37549850
Homo sapiens IC50 = 8580.0 nM 5.07 Concentration required to inhibit 50% growth of human Molt 4/C8 T-lymphocyte cel... 9544201
Unchecked IC50 = 8800.0 nM 5.06 Inhibition of PMA-induce ROS/RNS generation in human neutrophils measured up to ... 33006891
Homo sapiens IC50 = 9310.0 nM 5.03 Concentration required to inhibit 50% growth of Human CEM T-lymphocytes cells 9544201
Unchecked IC50 = 11600.0 nM 4.94 Inhibition of PMA-induce ROS/RNS generation in human neutrophils measured up to ... 33006891
SGC-7901 IC50 = 13740.0 nM 4.86 Cytotoxicity against Homo sapiens (human) SGC7901 cells after 72 hr by MTT assay -
P388 IC50 = 14300.0 nM 4.84 Inhibition of proliferation of murine P388 cells 9544201
Unchecked IC50 = 20000.0 nM 4.7 Inhibition of Escherichia coli GroEL expressed in NEB-5-alpha Escherichia coli c... 36356534
GroEL/GroES IC50 = 21000.0 nM 4.68 Inhibition of Escherichia coli GroEL expressed in Escherichia coliDH5alpha/Esche... 30852084
Unchecked IC50 = 21000.0 nM 4.68 Inhibition of human mitochondrial HSP60 expressed in Escherichia coli Rosetta 2 ... 36356534
HSP60/HSP10 IC50 = 22000.0 nM 4.66 Inhibition of human N-terminal octa-His-tagged HSP60 expressed in Escherichia co... 30852084
Nuclear factor NF-kappa-B complex IC50 = 24000.0 nM 4.62 Inhibition of NF-kappaB transactivation in TNF-alpha-stimulated human K562 cells... 24775915
HT-29 IC50 = 24600.0 nM 4.61 Cytotoxicity against Homo sapiens (human) HT-29 cells after 72 hr by MTT assay -
A549 IC50 = 26600.0 nM 4.58 Antiproliferative activity against human A549 cells assessed as cell growth inhi... 37666364
HCT-116 EC50 = 32000.0 nM 4.5 Cytotoxicity against p53-/- human HCT-116 cells assessed as reduction in cell vi... 36356534
HCT-116 EC50 = 32000.0 nM 4.5 Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability... 36356534
L1210 IC50 = 37900.0 nM 4.42 Concentration required to inhibit 50% growth of L1210 leukemia cells 9544201
HT-29 EC50 = 39000.0 nM 4.41 Cytotoxicity against human HT-29 cells assessed as reduction in cell viability i... 36356534
Unchecked IC50 = 39000.0 nM 4.41 Inhibition of Escherichia coli GroEL expressed in NEB-5-alpha Escherichia coli c... 36356534

Literature References

PubMed DOI Target Context # Activities
18280009 10.1016/j.ejmech.2007.12.027 Ogataea angusta 17
18280009 10.1016/j.ejmech.2007.12.027 Saccharomyces cerevisiae 13
36356534 10.1016/j.bmc.2022.117072 Unchecked 7
22727643 10.1016/j.bmcl.2012.05.112 Staphylococcus aureus 7
30852084 10.1016/j.bmcl.2019.02.028 Unchecked 5
- 10.1007/s00044-011-9549-9 Staphylococcus aureus 4
30852084 10.1016/j.bmcl.2019.02.028 GroEL/GroES 4
17007965 10.1016/j.ejmech.2006.08.012 Candida albicans 3
18280009 10.1016/j.ejmech.2007.12.027 Kluyveromyces lactis 3
- 10.1007/s00044-011-9549-9 Pseudomonas aeruginosa 2
- 10.1007/s00044-011-9549-9 Klebsiella pneumoniae 2
- 10.1007/s00044-011-9549-9 Acinetobacter baumannii 2
- 10.1007/s00044-011-9549-9 Escherichia coli 2
18584918 10.1016/j.ejmech.2008.05.010 Staphylococcus aureus 2
36356534 10.1016/j.bmc.2022.117072 HCT-116 2
- 10.1007/s00044-011-9549-9 Staphylococcus epidermidis 2
33006891 10.1021/acs.jnatprod.0c00728 Unchecked 2
37666364 10.1016/j.bmcl.2023.129467 A549 2
28655421 10.1016/j.bmcl.2017.01.053 No relevant target 2
9544201 10.1021/jm970432t Homo sapiens 2

Data from ChEMBL 36 via Core Engine