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Compound Detail

CHEMBL1078442

BERGAMOTTIN
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CC(C)=CCC/C(C)=C/COc1c2ccoc2cc2oc(=O)ccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1078442
Name BERGAMOTTIN
Phase Preclinical
Structure Type MOL
InChI Key DBMJZOMNXBSRED-OQLLNIDSSA-N
9
Targets
14
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

338.4
MW (Da)
5.61
ALogP
4
HBA
0
HBD
52.6
PSA (Ų)
0.43
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 C21H22O4
MW 338.40
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness 1.75

Activity Summary

Ki 9 meas. best 6.16
IC50 5 meas. best 5.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-secretase 1
CHEMBL4822
 Ki 6.16 5.31 700.0 2
Cytochrome P450 2B1
CHEMBL3335
 Ki 5.62 5.62 2400.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.62 5.62 2420.0 1
Cytochrome P450 2B4
CHEMBL1743542
 Ki 5.55 5.55 2800.0 1
Cytochrome P450 2B6
CHEMBL4729
 Ki 5.28 5.28 5200.0 1
Cytochrome P450 3A4
CHEMBL340
 Ki 5.11 5.11 7700.0 1
SARS-CoV-2
CHEMBL4303835
 IC50 5.09 4.97 8150.0 2
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 5.02 5.02 9640.0 1
Cytochrome P450 3A5
CHEMBL3019
 Ki 4.7 4.7 20000.0 1
Beta-secretase 1
CHEMBL4822
 IC50 4.49 4.49 32200.0 1
Cytochrome P450 2E1
CHEMBL5281
 Ki 4.4 4.4 40000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-secretase 1 Ki = 700.0 nM 6.16 Inhibition of recombinant human BACE1 assessed as dissociation constant of enzym... 22222157
Cytochrome P450 3A4 IC50 = 2420.0 nM 5.62 Inhibition of CYP3A4 after 30 mins by fluorescence microplate reader assay 19689106
Cytochrome P450 2B1 Ki = 2400.0 nM 5.62 Mechanism based inhibition of rat cytochrome P450 2B1 16248836
Cytochrome P450 2B4 Ki = 2800.0 nM 5.55 Mechanism based inhibition of rabbit cytochrome P450 2B4 16248836
Cytochrome P450 2B6 Ki = 5200.0 nM 5.28 Mechanism based inhibition of human cytochrome P450 2B6 16248836
Cytochrome P450 3A4 Ki = 7700.0 nM 5.11 Mechanism based inhibition of human cytochrome P450 3A4 measured by testosterone... 16248836
SARS-CoV-2 IC50 = 8150.0 nM 5.09 Antiviral activity against SARS-CoV-2 B.1.1.7 infected in human Calu-3 cells ass... 37597436
Replicase polyprotein 1ab IC50 = 9640.0 nM 5.02 Inhibition of SARS-CoV-2 3CL protease by FRET assay 37597436
SARS-CoV-2 IC50 = 14160.0 nM 4.85 Antiviral activity against SARS-CoV-2 Omicron B.1.351 Beta infected in human 293... 37597436
Cytochrome P450 3A5 Ki = 20000.0 nM 4.7 Mechanism based inhibition of human cytochrome P450 3A5 16248836
Beta-secretase 1 IC50 = 32200.0 nM 4.49 Inhibition of recombinant human BACE1 using Rh-EVNLDAEFK as substrate after 60 m... 22222157
Beta-secretase 1 Ki = 34800.0 nM 4.46 Inhibition of recombinant human BACE1 assessed as dissociation constant of enzym... 22222157
Cytochrome P450 2E1 Ki = 40000.0 nM 4.4 Mechanism based inhibition of human cytochrome P450 2E1 measured in vivo 16248836

Literature References

PubMed DOI Target Context # Activities
30070833 10.1021/acs.jnatprod.8b00405 PANC-1 13
22222157 10.1016/j.bmc.2011.12.002 Beta-secretase 1 4
21393461 10.1124/dmd.111.038208 Cytochrome P450 3A4 4
30070833 10.1021/acs.jnatprod.8b00405 MIA PaCa-2 3
16248836 10.2174/138920005774330639 Cytochrome P450 2B6 3
30070833 10.1021/acs.jnatprod.8b00405 PSN1 3
16248836 10.2174/138920005774330639 Cytochrome P450 3A4 3
16248836 10.2174/138920005774330639 Cytochrome P450 3A5 3
29730190 10.1016/j.ejmech.2018.04.051 Melan-a 3
15640378 10.1124/dmd.104.002337 Solute carrier organic anion transporter family member 2B1 2
30070833 10.1021/acs.jnatprod.8b00405 RAC-alpha serine/threonine-protein kinase 2
37597436 10.1016/j.ejmech.2023.115726 SARS-CoV-2 2
15504753 10.1038/sj.bjp.0706008 ATP-dependent translocase ABCB1 2
16248836 10.2174/138920005774330639 Cytochrome P450 2B1 2
16248836 10.2174/138920005774330639 Cytochrome P450 2B4 2
16248836 10.2174/138920005774330639 Cytochrome P450 2E1 2
10583025 10.1046/j.1365-2125.1999.00052.x ATP-dependent translocase ABCB1 1
10903978 10.1038/sj.bjp.0703433 ATP-dependent translocase ABCB1 1
19689106 10.1021/np900266m Cytochrome P450 3A4 1
11823753 10.1067/mcp.2002.121152 Solute carrier organic anion transporter family member 1A5 1

Data from ChEMBL 36 via Core Engine