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Compound Detail

CHEMBL378188

BILOBETIN
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COc1ccc(-c2cc(=O)c3c(O)cc(O)cc3o2)cc1-c1c(O)cc(O)c2c(=O)cc(-c3ccc(O)cc3)oc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL378188
Name BILOBETIN
Phase Preclinical
Structure Type MOL
InChI Key IWEIJEPIYMAGTH-UHFFFAOYSA-N
7
Targets
8
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

552.5
MW (Da)
5.44
ALogP
10
HBA
5
HBD
170.8
PSA (Ų)
0.19
QED
2
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C31H20O10
MW 552.49
Aromatic Rings 6
Heavy Atoms 41
NP-Likeness 1.13

Activity Summary

IC50 7 meas. best 6.44
Ki 1 meas. best 4.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 6.44 6.44 360.0 1
Beta-secretase 1
CHEMBL4822
 IC50 5.7 5.7 2020.0 1
Leishmania donovani
CHEMBL367
 IC50 5.57 5.57 2700.0 1
Amyloid-beta precursor protein
CHEMBL2487
 IC50 5.33 5.33 4700.0 1
Matrix metalloproteinase-9
CHEMBL321
 IC50 4.99 4.99 10330.0 1
MCF7
CHEMBL387
 IC50 4.58 4.58 26500.0 1
Replicase polyprotein 1ab
CHEMBL5118
 IC50 4.14 4.14 72300.0 1
Replicase polyprotein 1ab
CHEMBL5118
 Ki 4.09 4.09 80400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 360.0 nM 6.44 Inhibition of PDE in Sprague-Dawley rat epididymal adipose tissue assessed as [1... 9834158
Beta-secretase 1 IC50 = 2020.0 nM 5.7 Inhibition of BACE1 after 60 mins by FRET assay 20598535
Leishmania donovani IC50 = 2700.0 nM 5.57 Antimicrobial activity against axenically grown Leishmania donovani amastigotes 22989363
Amyloid-beta precursor protein IC50 = 4700.0 nM 5.33 Inhibition of human amyloid beta (1 to 40) assessed as reduction in aggregation ... 31138471
Matrix metalloproteinase-9 IC50 = 10330.0 nM 4.99 Inhibition of recombinant human MMP9 preincubated for 30 mins followed by McaPro... 29921475
MCF7 IC50 = 26500.0 nM 4.58 Cytotoxicity against human MCF7 cells measured after 24 hrs by MTT assay 34875389
Replicase polyprotein 1ab IC50 = 72300.0 nM 4.14 Inhibition of SARS coronavirus 3C-like protease after 60 mins by FRET assay 20934345
Replicase polyprotein 1ab Ki = 80400.0 nM 4.09 Non-competitive inhibition of SARS coronavirus 3C-like protease by Dixon plot an... 20934345

Literature References

PubMed DOI Target Context # Activities
36700552 10.1021/acs.jnatprod.2c00959 HCT-116 27
36700552 10.1021/acs.jnatprod.2c00959 Unchecked 13
16574412 10.1016/j.bmcl.2006.03.018 Osteoblast 4
36700552 10.1021/acs.jnatprod.2c00959 Cellular tumor antigen p53 2
9834158 10.1021/np970569m Unchecked 2
20934345 10.1016/j.bmc.2010.09.035 Replicase polyprotein 1ab 2
29921475 10.1016/j.bmcl.2018.06.024 T-24 1
36700552 10.1021/acs.jnatprod.2c00959 LoVo 1
36700552 10.1021/acs.jnatprod.2c00959 RKO 1
34875389 10.1016/j.bmcl.2021.128486 MCF7 1
31138471 10.1016/j.bmcl.2019.05.020 Amyloid-beta precursor protein 1
29921475 10.1016/j.bmcl.2018.06.024 Matrix metalloproteinase-9 1
29921475 10.1016/j.bmcl.2018.06.024 Stromelysin-1 1
29921475 10.1016/j.bmcl.2018.06.024 72 kDa type IV collagenase 1
29921475 10.1016/j.bmcl.2018.06.024 A549 1
29921475 10.1016/j.bmcl.2018.06.024 HepG2 1
29921475 10.1016/j.bmcl.2018.06.024 MGC-803 1
26004578 10.1016/j.bmcl.2015.04.106 NON-PROTEIN TARGET 1
22989363 10.1021/jm301172v Leishmania donovani 1
20598535 10.1016/j.bmcl.2010.06.021 Beta-secretase 1 1

Data from ChEMBL 36 via Core Engine