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Compound Detail

CHEMBL393417

DEGUELIN
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COc1cc2c(cc1OC)[C@@H]1C(=O)c3ccc4c(c3O[C@@H]1CO2)C=CC(C)(C)O4
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL393417
Name DEGUELIN
Phase Preclinical
Structure Type MOL
InChI Key ORDAZKGHSNRHTD-UXHICEINSA-N
9
Targets
17
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

394.4
MW (Da)
4.01
ALogP
6
HBA
0
HBD
63.2
PSA (Ų)
0.77
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C23H22O6
MW 394.42
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness 2.26

Activity Summary

IC50 17 meas. best 7.97

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 7.97 6.7967 10.6 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.96 5.6875 110.0 4
L5178Y
CHEMBL614720
 IC50 6.7 6.7 200.0 1
Human orthopneumovirus
CHEMBL613127
 IC50 6.4 6.4 400.0 1
Heat shock protein HSP 90-alpha
CHEMBL3880
 IC50 5.79 5.79 1630.0 1
NCI-H1299
CHEMBL612255
 IC50 5.25 5.25 5670.0 1
U-937
CHEMBL612794
 IC50 5.24 4.8067 5800.0 3
A549
CHEMBL392
 IC50 5.22 5.22 6050.0 1
MCF7
CHEMBL387
 IC50 5.09 5.09 8170.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 10.6 nM 7.97 Inhibition of complex 1 in bovine heart mitochondrial membranes in presence of N... 32459967
NON-PROTEIN TARGET IC50 = 110.0 nM 6.96 Cytotoxicity against human H1299 cells after 3 days by MTS assay 23186287
L5178Y IC50 = 200.0 nM 6.7 Cytotoxicity against mouse L5178Y cells by MTT assay 28075580
Unchecked IC50 = 220.0 nM 6.66 Inhibition of TNF-alpha-induced NF-kappaB activation in human HeLa cells by SEAP... 18841906
Human orthopneumovirus IC50 = 400.0 nM 6.4 Antiviral activity against Human respiratory syncytial virus infected in human H... 38579352
NON-PROTEIN TARGET IC50 = 1200.0 nM 5.92 Growth inhibition of Nf1 defective and Trp53 defective mouse K5001 cells after 2... 26467198
Heat shock protein HSP 90-alpha IC50 = 1630.0 nM 5.79 Inhibition of FITC-geldanamycin binding to recombinant human full-length C-termi... 30784881
Unchecked IC50 = 1750.0 nM 5.76 Inhibition of LPS-induced NF-kappaB activation in mouse RAW264.7 cells by SEAP r... 18841906
NCI-H1299 IC50 = 5670.0 nM 5.25 Antiproliferative activity against human NCI-H1299 cells after 72 hrs by MTT ass... 30784881
U-937 IC50 = 5800.0 nM 5.24 Antiproliferative activity against human U937 cells after 72 hrs by WST-8 assay 17158054
A549 IC50 = 6050.0 nM 5.22 Antiproliferative activity against human A549 cells after 72 hrs by MTT assay 30784881
MCF7 IC50 = 8170.0 nM 5.09 Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay 30784881
NON-PROTEIN TARGET IC50 = 10590.0 nM 4.97 Cytotoxicity against human MCF7 cells assessed as cell growth inhibition after 2... 27376493
NON-PROTEIN TARGET IC50 = 12600.0 nM 4.9 Growth inhibition of Nf1 defective and Trp53 defective mouse KR158 cells after 2... 26467198
U-937 IC50 = 16000.0 nM 4.8 Antiproliferative activity against human U937 cells after 48 hrs by WST-8 assay 17158054
U-937 IC50 = 42000.0 nM 4.38 Antiproliferative activity against human U937 cells after 24 hrs by WST-8 assay 17158054

Literature References

PubMed DOI Target Context # Activities
17158054 10.1016/j.bmc.2006.09.024 HT-1080 30
22970736 10.1021/jf3032217 Callosobruchus maculatus 6
27584977 10.1021/acs.jnatprod.6b00444 NON-PROTEIN TARGET 6
26467198 10.1021/acs.jnatprod.5b00753 Unchecked 5
30784881 10.1016/j.ejmech.2019.02.014 NCI-H1299 4
17158054 10.1016/j.bmc.2006.09.024 HL-60 4
17158054 10.1016/j.bmc.2006.09.024 U-937 3
26467198 10.1021/acs.jnatprod.5b00753 NON-PROTEIN TARGET 3
23186287 10.1021/jm301488q Danio rerio 3
30827868 10.1016/j.bmc.2019.02.040 Heat shock protein HSP90 2
26457742 10.1016/j.ejmech.2015.09.033 Hypoxia-inducible factor 1-alpha 2
26467198 10.1021/acs.jnatprod.5b00753 RAC-alpha serine/threonine-protein kinase 2
30910460 10.1016/j.bmcl.2019.03.024 Cholinesterase 2
27745993 10.1016/j.bmc.2016.09.067 Heat shock protein HSP90 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
18841906 10.1021/np800383q Unchecked 2
30910460 10.1016/j.bmcl.2019.03.024 Acetylcholinesterase 2
27745993 10.1016/j.bmc.2016.09.067 NON-PROTEIN TARGET 2
38579352 10.1021/acs.jnatprod.3c01288 HEp-2 2
11975515 10.1021/np010126p Helicobacter pylori 1

Data from ChEMBL 36 via Core Engine