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Compound Detail

CHEMBL273019

BERGENIN
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COc1c(O)cc2c(c1O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1OC2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL273019
Name BERGENIN
Phase Preclinical
Structure Type MOL
InChI Key YWJXCIXBAKGUKZ-HJJNZUOJSA-N

Known Names

Bergenin Bergeninum NSC-661749 NSC-757796 Yanbaicaisu
8
Targets
14
Activities
1
Assay Types
0
PK Parameters
20
Publications
5
Known Names

Molecular Properties

328.3
MW (Da)
-1.20
ALogP
9
HBA
5
HBD
145.9
PSA (Ų)
0.42
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -erg-

Extended Properties

Molecular Formula C14H16O9
MW 328.27
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness 2.63

Activity Summary

IC50 14 meas. best 9.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
No relevant target
CHEMBL2362975
 IC50 9.27 9.27 0.5 1
Interleukin-6
CHEMBL1795129
 IC50 6.68 6.68 208.0 1
THP-1
CHEMBL614245
 IC50 6.68 5.22 208.0 3
Tumor necrosis factor
CHEMBL1825
 IC50 4.9 4.9 12500.0 1
Unchecked
CHEMBL612545
 IC50 4.66 4.66 21700.0 1
SGC-7901
CHEMBL614909
 IC50 4.63 4.63 23560.0 1
HepG2
CHEMBL395
 IC50 4.46 4.46 34560.0 1
A549
CHEMBL392
 IC50 4.11 4.11 77280.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
No relevant target IC50 = 0.54 nM 9.27 Antiglycation activity assessed as inhibition of Schiff-base formation 21752643
THP-1 IC50 = 208.0 nM 6.68 Inhibition of LPS-induced IL6 production in human THP1 cells after 24 hrs 25111439
Interleukin-6 IC50 = 208.0 nM 6.68 Inhibition of IL6 (unknown origin) 28843845
THP-1 IC50 = 12500.0 nM 4.9 Inhibition of LPS-induced TNFalpha production in human THP1 cells after 24 hrs 25111439
Tumor necrosis factor IC50 = 12500.0 nM 4.9 Inhibition of TNFalpha (unknown origin) 28843845
Unchecked IC50 = 21700.0 nM 4.66 Inhibition of Sporosarcina pasteurii urease using urea as substrate after 15 min -
SGC-7901 IC50 = 23560.0 nM 4.63 Antiproliferative activity against human SGC7901 cells incubated for 48 to 72 hr... 28395218
HepG2 IC50 = 34560.0 nM 4.46 Antiproliferative activity against human HepG2 cells incubated for 48 to 72 hrs ... 28395218
A549 IC50 = 77280.0 nM 4.11 Antiproliferative activity against human A549 cells incubated for 48 to 72 hrs b... 28395218
THP-1 IC50 = 84000.0 nM 4.08 Cytotoxicity against human THP1 cells after 48 hrs by MTT assay 25111439

Literature References

PubMed DOI Target Context # Activities
21939182 10.1021/np200232s Mus musculus 46
25111439 10.1021/jm500901e Mus musculus 20
28843845 10.1016/j.bmc.2017.08.011 No relevant target 13
8786362 10.1021/np960074h Unchecked 8
25111439 10.1021/jm500901e THP-1 8
9722485 10.1021/np980107o Unchecked 6
27374242 10.1016/j.bmcl.2016.06.054 RAW264.7 6
21752643 10.1016/j.bmcl.2011.04.131 No relevant target 5
17997321 10.1016/j.bmc.2007.10.072 BGC-823 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
34825192 10.1039/D1MD00210D Unchecked 3
- 10.1007/s00044-011-9762-6 Unchecked 2
24268551 10.1016/j.bmcl.2013.10.066 Tyrosinase 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
21752643 10.1016/j.bmcl.2011.04.131 Albumin 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
9722485 10.1021/np980107o No relevant target 2
21474216 10.1016/j.ejmech.2011.03.025 Klebsiella pneumoniae 1
21474216 10.1016/j.ejmech.2011.03.025 Escherichia coli 1
36940609 10.1016/j.bmc.2023.117239 Chikungunya virus 1

Data from ChEMBL 36 via Core Engine