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Compound Detail

CHEMBL374130

BONANNIONE A
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CC(C)=CCC/C(C)=C/Cc1c(O)cc2c(c1O)C(=O)C[C@@H](c1ccc(O)cc1)O2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL374130
Name BONANNIONE A
Phase Preclinical
Structure Type MOL
InChI Key XYIQIBWIEGCVQY-RWHUQTJRSA-N
10
Targets
13
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

408.5
MW (Da)
5.75
ALogP
5
HBA
3
HBD
87.0
PSA (Ų)
0.53
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C25H28O5
MW 408.49
Aromatic Rings 2
Heavy Atoms 30
NP-Likeness 2.29

Activity Summary

IC50 9 meas. best 5.43
Ki 3 meas. best 5.11
EC50 1 meas. best 4.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tumour suppressor p53/oncoprotein Mdm2
CHEMBL1907611
 IC50 5.43 5.43 3700.0 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 5.43 5.43 3700.0 1
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 5.22 5.22 6000.0 1
Unchecked
CHEMBL612545
 Ki 5.11 5.11 7800.0 1
CCRF-CEM
CHEMBL382
 EC50 4.94 4.94 11600.0 1
Unchecked
CHEMBL612545
 IC50 4.84 4.84 14400.0 1
Molecular identity unknown
CHEMBL612546
 IC50 4.84 4.84 14600.0 1
Butyrylcholinesterase
CHEMBL5077
 IC50 4.69 4.69 20600.0 1
Butyrylcholinesterase
CHEMBL5077
 Ki 4.65 4.65 22200.0 1
A2780cisR
CHEMBL614023
 IC50 4.61 4.61 24500.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.52 4.52 29900.0 1
Acetylcholinesterase
CHEMBL220
 IC50 4.04 4.04 91500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 1 IC50 = 3700.0 nM 5.43 Inhibition of ram seminal vesicle COX1 assessed as reduction in PGE2 formation p... 28322565
Tumour suppressor p53/oncoprotein Mdm2 IC50 = 3700.0 nM 5.43 Inhibition of MDM2/p53 interaction (unknown origin) 38295689
Prostaglandin G/H synthase 2 IC50 = 6000.0 nM 5.22 Inhibition of human recombinant COX2 assessed as reduction in PGE2 formation pre... 28322565
Unchecked Ki = 7800.0 nM 5.11 Mixed-type of inhibition of SARS coronavirus papain-like protease (1541 to 1855 ... 23623680
CCRF-CEM EC50 = 11600.0 nM 4.94 Cytotoxicity against human CEM cells assessed as viable cells after 72 hrs by ca... 20192247
Unchecked IC50 = 14400.0 nM 4.84 Inhibition of SARS coronavirus papain-like protease (1541 to 1855 amino acids) e... 23623680
Molecular identity unknown IC50 = 14600.0 nM 4.84 Inhibition of hedgehog signaling pathway in human HaCaT cells assessed as GLI1-m... 26178912
Butyrylcholinesterase IC50 = 20600.0 nM 4.69 Inhibition of equine BChE assessed as butyrylthiocholine iodide hydrolysis after... 22445674
Butyrylcholinesterase Ki = 22200.0 nM 4.65 Mixed type inhibition of equine BChE using butyrylthiocholine iodide as substrat... 22445674
A2780cisR IC50 = 24500.0 nM 4.61 Antiproliferative activity against drug-sensitive human A2780 cells 17326683
NON-PROTEIN TARGET IC50 = 29900.0 nM 4.52 Cytotoxicity against Hh signaling abnormally activated human PANC1 cells after 2... 26178912
Acetylcholinesterase IC50 = 91500.0 nM 4.04 Inhibition of human erythrocyte AChE assessed as acetylthiocholine iodide hydrol... 22445674

Literature References

PubMed DOI Target Context # Activities
22445674 10.1016/j.bmc.2012.02.044 Acetylcholinesterase 4
17625893 10.1021/np070063w ADMET 3
23623680 10.1016/j.bmc.2013.03.027 Unchecked 3
22445674 10.1016/j.bmc.2012.02.044 Butyrylcholinesterase 2
26178912 10.1016/j.bmc.2015.06.058 Molecular identity unknown 2
25735399 10.1021/acs.jnatprod.5b00005 THP-1 2
28322565 10.1021/acs.jnatprod.6b01011 Prostaglandin G/H synthase 2 2
18293924 10.1021/np070446u Staphylococcus epidermidis 1
17326683 10.1021/np060484y A2780cisR 1
20192247 10.1021/np900681y HeLa 1
20192247 10.1021/np900681y U-266 1
17625893 10.1021/np070063w Radical scavenging activity 1
20192247 10.1021/np900681y MCF7 1
15787448 10.1021/np049639x A2780 1
38295689 10.1016/j.ejmech.2023.116117 Tumour suppressor p53/oncoprotein Mdm2 1
18293924 10.1021/np070446u Staphylococcus aureus 1
18293924 10.1021/np070446u Listeria monocytogenes 1
18293924 10.1021/np070446u Bacillus subtilis 1
18293924 10.1021/np070446u Bacillus cereus 1
18293924 10.1021/np070446u Salmonella enteritidis 1

Data from ChEMBL 36 via Core Engine