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Compound Detail

CHEMBL253467

ISOBAVACHALCONE
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CC(C)=CCc1c(O)ccc(C(=O)/C=C/c2ccc(O)cc2)c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL253467
Name ISOBAVACHALCONE
Phase Preclinical
Structure Type MOL
InChI Key DUWPGRAKHMEPCM-IZZDOVSWSA-N
11
Targets
19
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

324.4
MW (Da)
4.21
ALogP
4
HBA
3
HBD
77.8
PSA (Ų)
0.44
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H20O4
MW 324.38
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 1.41

Activity Summary

IC50 17 meas. best 6.89
EC50 1 meas. best 4.29
Ki 1 meas. best 5.31

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL1966
 IC50 6.89 6.89 130.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.3 4.9567 500.0 3
Unchecked
CHEMBL612545
 IC50 5.85 5.2275 1400.0 4
RAW264.7
CHEMBL612557
 IC50 5.8 5.26 1600.0 3
Unchecked
CHEMBL612545
 Ki 5.31 5.31 4900.0 1
OVCAR-8
CHEMBL612555
 IC50 5.1 5.1 7920.0 1
PC-3
CHEMBL390
 IC50 4.82 4.82 15060.0 1
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
 IC50 4.56 4.56 27300.0 1
K562
CHEMBL385
 IC50 4.53 4.53 29490.0 1
SW480
CHEMBL612544
 IC50 4.36 4.36 44070.0 1
SARS-CoV-2
CHEMBL4303835
 EC50 4.29 4.29 51500.0 1
HCT-116
CHEMBL394
 IC50 4.12 4.12 75480.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 130.0 nM 6.89 Inhibition of human DHODH 35151222
NON-PROTEIN TARGET IC50 = 500.0 nM 6.3 Antiplatelet activity against rabbit platelet assessed as inhibition of arachido... 8759164
Unchecked IC50 = 1400.0 nM 5.85 Inhibition of melanin synthesis in NHEM after 24 hrs by liquid scintillation 19102656
RAW264.7 IC50 = 1600.0 nM 5.8 Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells 32208222
Unchecked IC50 = 3300.0 nM 5.48 Inhibition of porcine pancreatic lipase type 2 33214035
Unchecked Ki = 4900.0 nM 5.31 Mixed inhibition of SARS-CoV N-terminal 6His-tagged TEV-fused papain-like protea... 32845145
RAW264.7 IC50 = 6400.0 nM 5.19 Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells assess... 16643064
Unchecked IC50 = 7300.0 nM 5.14 Inhibition of SARS-CoV N-terminal 6His-tagged TEV-fused papain-like protease exp... 32845145
OVCAR-8 IC50 = 7920.0 nM 5.1 Cytotoxicity against human OVCAR-8 cells assessed as cell growth inhibition meas... 35151222
PC-3 IC50 = 15060.0 nM 4.82 Cytotoxicity against human PC3 cells assessed as cell growth inhibition measured... 35151222
RAW264.7 IC50 = 16400.0 nM 4.79 Cytotoxicity against mouse RAW264.7 cells by MTT assay 16643064
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 27300.0 nM 4.56 Inhibition of PTP1B (unknown origin) using p-nitrophenyl phosphate as substrate 24047800
K562 IC50 = 29490.0 nM 4.53 Antitumor activity against human K562 cells incubated for 48 hrs by MTT assay 25590864
Unchecked IC50 = 36000.0 nM 4.44 Inhibition of porcine heart MDH using oxaloacetic acid as substrate preincubated... 38864383
NON-PROTEIN TARGET IC50 = 41600.0 nM 4.38 Antiplatelet activity against rabbit platelet assessed as inhibition of platelet... 8759164
SW480 IC50 = 44070.0 nM 4.36 Antiproliferative activity against human SW480 cells assessed as reduction in ce... 33445154
SARS-CoV-2 EC50 = 51500.0 nM 4.29 Antiviral activity against SARS-CoV-2 pseudotyped lentivirus infected in HEK293 ... 38864383
NON-PROTEIN TARGET IC50 = 65100.0 nM 4.19 Antiplatelet activity against rabbit platelet assessed as inhibition of collagen... 8759164
HCT-116 IC50 = 75480.0 nM 4.12 Antiproliferative activity against human HCT-116 cells assessed as reduction in ... 33445154

Literature References

PubMed DOI Target Context # Activities
20160051 10.1128/aac.01533-09 Klebsiella aerogenes 16
22169259 10.1016/j.bmcl.2011.11.059 Staphylococcus aureus 15
37210837 10.1016/j.ejmech.2023.115454 Pseudomonas aeruginosa 13
20160051 10.1128/aac.01533-09 Escherichia coli 12
20160051 10.1128/aac.01533-09 Klebsiella pneumoniae 6
16441065 10.1021/np058080d Unchecked 6
37659218 10.1016/j.bmc.2023.117454 Staphylococcus aureus 6
38864383 10.1021/acs.jmedchem.4c00597 Unchecked 4
20160051 10.1128/aac.01533-09 Enterobacter cloacae 4
20160051 10.1128/aac.01533-09 Pseudomonas aeruginosa 4
20304658 10.1016/j.bmc.2010.02.055 Parabodo caudatus 3
8759164 10.1021/np960157y NON-PROTEIN TARGET 3
22169259 10.1016/j.bmcl.2011.11.059 Vero 3
16643064 10.1021/np0600346 RAW264.7 3
3069957 10.1021/np50060a006 Salmonella typhimurium 3
38864383 10.1021/acs.jmedchem.4c00597 No relevant target 3
24047800 10.1016/j.bmcl.2013.08.102 Tyrosine-protein phosphatase non-receptor type 1 2
18951808 10.1016/j.bmc.2008.09.064 Staphylococcus aureus 2
24953601 10.1016/j.bmcl.2014.05.077 No relevant target 2
32845145 10.1021/acs.jmedchem.0c00626 Unchecked 2

Data from ChEMBL 36 via Core Engine