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Compound Detail

CHEMBL233929

GALUTEOLIN
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O=c1cc(-c2ccc(O)c(O)c2)oc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)cc(O)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL233929
Name GALUTEOLIN
Phase Preclinical
Structure Type MOL
InChI Key PEFNSGRTCBGNAN-QNDFHXLGSA-N
13
Targets
24
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

448.4
MW (Da)
-0.24
ALogP
11
HBA
7
HBD
190.3
PSA (Ų)
0.26
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 C21H20O11
MW 448.38
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness 1.97

Activity Summary

IC50 15 meas. best 5.21
EC50 6 meas. best 5.41
Kd 3 meas. best 8.01

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Kd 8.01 8.01 9.9 1
Interleukin-2
CHEMBL5880
 Kd 7.7 7.7 20.0 1
Tumor necrosis factor
CHEMBL1825
 Kd 6.1 6.1 790.0 1
Radical scavenging activity
CHEMBL613712
 EC50 5.41 5.41 3940.0 1
H9c2
CHEMBL614576
 EC50 5.3 5.3 5040.0 1
RAW264.7
CHEMBL612557
 IC50 5.21 4.7833 6100.0 3
Human immunodeficiency virus 1
CHEMBL378
 EC50 5.16 5.16 7000.0 1
HepG2
CHEMBL395
 IC50 4.68 4.68 20800.0 1
H9
CHEMBL614806
 IC50 4.6 4.6 25000.0 1
Unchecked
CHEMBL612545
 IC50 4.5 4.37 32000.0 2
Neuraminidase
CHEMBL6135
 IC50 4.32 4.2767 47400.0 3
Neuraminidase
CHEMBL3559643
 IC50 4.29 4.235 51200.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 4.25 4.25 56460.0 1
Xanthine dehydrogenase/oxidase
CHEMBL3649
 IC50 4.12 4.12 75900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Kd = 9.89 nM 8.01 Binding affinity to Bcl-xL (unknown origin) 24974349
Interleukin-2 Kd = 20.0 nM 7.7 Binding affinity to IL-2 (unknown origin) 24974349
Tumor necrosis factor Kd = 790.0 nM 6.1 Binding affinity to TNF-alpha (unknown origin) 24974349
Radical scavenging activity EC50 = 3940.0 nM 5.41 Antioxidant activity of the compound assessed as DPPH radical scavenging activit... 20932762
H9c2 EC50 = 5040.0 nM 5.3 Cytoprotective activity against doxorubicin-induced cytotoxicity in rat H9c2 cel... 20932762
RAW264.7 IC50 = 6100.0 nM 5.21 Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed a... 31747281
Human immunodeficiency virus 1 EC50 = 7000.0 nM 5.16 Antiviral activity against HIV1 3B infected in human H9 cells assessed as inhibi... 8158164
RAW264.7 IC50 = 8300.0 nM 5.08 Inhibition of NO production in LPS-stimulated mouse RAW264.7 cells pre-incubated... 25176187
HepG2 IC50 = 20800.0 nM 4.68 Anticancer activity against human HepG2 cells assessed as cell viability after 2... 24974349
H9 IC50 = 25000.0 nM 4.6 Cytotoxicity against human H9 cells after 3 days 8158164
Unchecked IC50 = 32000.0 nM 4.5 Inhibition of biotinylated 5-(4-((Z)-3-Carboxy-3-hydroxyacryloyl)-4-(4-chloroben... 32883638
Neuraminidase IC50 = 47400.0 nM 4.32 Inhibition of Influenza A PR/8/34 H1N1 virus neuraminidase activity by MUN-ANA s... 18640042
Neuraminidase IC50 = 51200.0 nM 4.29 Inhibition of influenza A virus (A/Perth/16/2009(H3N2)) neuraminidase using MUNA... 25096296
Neuraminidase IC50 = 52200.0 nM 4.28 Inhibition of Influenza A Jinan/15/90 H3N2 virus neuraminidase activity by MUN-A... 18640042
NON-PROTEIN TARGET EC50 = 56460.0 nM 4.25 Antioxidant activity assessed as ABTS radical scavenging activity 20932762
Unchecked IC50 = 57200.0 nM 4.24 Inhibition of influenza B virus (B/Brisbane/60/2008) neuraminidase using MUNANA ... 25096296
Neuraminidase IC50 = 58600.0 nM 4.23 Inhibition of Influenza A Jiangsu/10/2003 virus neuraminidase activity by MUN-AN... 18640042
Neuraminidase IC50 = 66600.0 nM 4.18 Inhibition of influenza A virus (A/California/07/2009(H1N1)) pdm09 neuraminidase... 25096296
Xanthine dehydrogenase/oxidase IC50 = 75900.0 nM 4.12 Inhibition of cow milk xanthine oxidase 3379415
RAW264.7 IC50 = 87500.0 nM 4.06 Inhibition of LPS induced NO production in mouse RAW264.7 cells measured after 2... 33667099

Literature References

PubMed DOI Target Context # Activities
3430163 10.1021/np50052a004 Hepatocyte 8
20932762 10.1016/j.bmcl.2010.09.086 H9c2 8
25987378 10.1016/j.bmcl.2015.04.052 Unchecked 6
28479197 10.1016/j.bmcl.2017.04.076 Thoracic aorta 5
25987378 10.1016/j.bmcl.2015.04.052 ADMET 5
25497988 10.1016/j.bmcl.2014.11.054 RAW264.7 4
9287421 10.1021/np970011e Platelet 4
18640042 10.1016/j.bmc.2008.06.049 Neuraminidase 3
28248102 10.1021/acs.jnatprod.6b01026 SH-SY5Y 3
28479197 10.1016/j.bmcl.2017.04.076 Unchecked 3
9287421 10.1021/np970011e Aorta 3
37099836 10.1016/j.ejmech.2023.115391 HepG2 3
20116898 10.1016/j.ejmech.2010.01.005 Neuraminidase 2
6677714 10.1021/np50030a007 Escherichia coli 2
3379415 10.1021/np50056a030 Xanthine dehydrogenase/oxidase 2
19944611 10.1016/j.bmc.2009.11.015 No relevant target 2
25987378 10.1016/j.bmcl.2015.04.052 Tyrosinase 2
7775983 10.1021/np50117a005 Unchecked 2
25096296 10.1016/j.bmcl.2014.07.010 Unchecked 2
18640042 10.1016/j.bmc.2008.06.049 MDCK 2

Data from ChEMBL 36 via Core Engine