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Compound Detail

CHEMBL447565

ALPHA-HEDERIN
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C[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@H]3CC[C@@]4(C)[C@@H](CC[C@]5(C)[C@@H]4CC=C4[C@@H]6CC(C)(C)CC[C@]6(C(=O)O)CC[C@]45C)[C@]3(C)CO)OC[C@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL447565
Name ALPHA-HEDERIN
Phase Preclinical
Structure Type MOL
InChI Key KEOITPILCOILGM-LLJOFIFVSA-N
14
Targets
24
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

751.0
MW (Da)
3.52
ALogP
11
HBA
7
HBD
195.6
PSA (Ų)
0.15
QED
3
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 C41H66O12
MW 750.97
Aromatic Rings 0
Heavy Atoms 53
NP-Likeness 2.99

Activity Summary

IC50 22 meas. best 5.96
EC50 2 meas. best 6.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trachea
CHEMBL4296542
 EC50 6.0 6.0 1000.0 1
RAW264.7
CHEMBL612557
 IC50 5.96 5.96 1100.0 1
No relevant target
CHEMBL2362975
 EC50 5.4 5.4 4000.0 1
Unchecked
CHEMBL612545
 IC50 5.26 5.26 5500.0 1
SMMC-7721
CHEMBL613831
 IC50 4.97 4.97 10800.0 1
ADMET
CHEMBL612558
 IC50 4.94 4.6933 11500.0 3
HL-60
CHEMBL383
 IC50 4.93 4.93 11780.0 1
A549
CHEMBL392
 IC50 4.91 4.69 12290.0 4
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.88 4.82 13200.0 2
HepG2
CHEMBL395
 IC50 4.79 4.79 16340.0 1
L02
CHEMBL4296457
 IC50 4.68 4.68 20980.0 1
HeLa
CHEMBL399
 IC50 4.67 4.67 21180.0 1
ECV-304
CHEMBL614035
 IC50 4.54 4.5 29000.0 4
DLD-1
CHEMBL614285
 IC50 4.42 4.32 38000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trachea EC50 = 1000.0 nM 6.0 Inhibition of carbachol-induced contraction of Sprague-Dawley rat tracheal rings... 24761833
RAW264.7 IC50 = 1100.0 nM 5.96 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 31301930
No relevant target EC50 = 4000.0 nM 5.4 Reduction in surface tension in 0.1 M PBS after 10 mins by Wilhelmy plate method... 22503361
Unchecked IC50 = 5500.0 nM 5.26 Inhibition of TNF-alpha-induced NFkappaB activation in human HepG2 cells after 1... 21870831
SMMC-7721 IC50 = 10800.0 nM 4.97 Cytotoxicity against human SMMC7721 cells assessed as inhibition of cell growth ... 25958248
ADMET IC50 = 11500.0 nM 4.94 Cytotoxicity against human HL7702 cells assessed as inhibition of cell growth af... 25958248
HL-60 IC50 = 11780.0 nM 4.93 Cytotoxicity against human HL60 cells assessed as cell viability after 72 hrs by... 23992864
A549 IC50 = 12290.0 nM 4.91 Cytotoxicity against human A549 cells assessed as cell viability after 72 hrs by... 23992864
NON-PROTEIN TARGET IC50 = 13200.0 nM 4.88 Cytotoxicity against human Bel7402 cells assessed as inhibition of cell growth a... 25958248
A549 IC50 = 15300.0 nM 4.82 Cytotoxicity against human A549 cells assessed as inhibition of cell growth afte... 25958248
HepG2 IC50 = 16340.0 nM 4.79 Cytotoxicity against human HepG2 cells assessed as cell viability after 72 hrs b... 23992864
NON-PROTEIN TARGET IC50 = 17340.0 nM 4.76 Cytotoxicity against human U87MG cells assessed as cell viability after 72 hrs b... 23992864
L02 IC50 = 20980.0 nM 4.68 Cytotoxicity against human L02 cells by MTT assay 33964439
HeLa IC50 = 21180.0 nM 4.67 Cytotoxicity against human HeLa cells assessed as cell viability after 72 hrs by... 23992864
ADMET IC50 = 24000.0 nM 4.62 Cell membrane permeabilization in human WS1 cells assessed as drug level causing... 19200744
A549 IC50 = 28000.0 nM 4.55 Cell membrane permeabilization in human A549 cells assessed as drug level causin... 19200744
ECV-304 IC50 = 29000.0 nM 4.54 Membranolytic activity in human ECV304 cells assessed as leakage of intracellula... 22503361
ECV-304 IC50 = 29000.0 nM 4.54 Membrane toxicity against human ECV304 cells after 2 hrs by LDH release assay 24084294
ADMET IC50 = 30000.0 nM 4.52 Cytotoxicity against human WS1 cells after 48 hrs by resazurin reduction test 19200744
A549 IC50 = 33000.0 nM 4.48 Cytotoxicity against human A549 cells after 48 hrs by resazurin reduction test 19200744

Literature References

PubMed DOI Target Context # Activities
33964439 10.1016/j.bmcl.2021.128080 L02 17
24084294 10.1016/j.bmc.2013.09.008 ECV-304 4
31301930 10.1016/j.bmcl.2019.07.010 RAW264.7 3
25958248 10.1016/j.bmcl.2015.04.049 ADMET 3
19200744 10.1016/j.bmc.2009.01.022 ADMET 3
21870831 10.1021/np200382s Unchecked 3
22503361 10.1016/j.bmc.2012.03.032 No relevant target 2
33479679 10.1039/d0md00123f Leishmania mexicana 2
22503361 10.1016/j.bmc.2012.03.032 ECV-304 2
19200744 10.1016/j.bmc.2009.01.022 DLD-1 2
19200744 10.1016/j.bmc.2009.01.022 A549 2
33964439 10.1016/j.bmcl.2021.128080 No relevant target 2
21870831 10.1021/np200382s HepG2 1
11170676 10.1021/np0003589 Candida albicans 1
23992864 10.1016/j.bmcl.2013.08.006 NON-PROTEIN TARGET 1
23992864 10.1016/j.bmcl.2013.08.006 HeLa 1
23992864 10.1016/j.bmcl.2013.08.006 A549 1
23992864 10.1016/j.bmcl.2013.08.006 HL-60 1
24761833 10.1021/np4008969 Trachea 1
10514313 10.1021/np9901837 HL-60 1

Data from ChEMBL 36 via Core Engine