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Compound Detail

CHEMBL487017

APIGETRIN
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O=c1cc(-c2ccc(O)cc2)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 CHEMBL487017
Name APIGETRIN
Phase Preclinical
Structure Type MOL
InChI Key KMOUJOKENFFTPU-QNDFHXLGSA-N
15
Targets
22
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

432.4
MW (Da)
0.05
ALogP
10
HBA
6
HBD
170.1
PSA (Ų)
0.33
QED
1
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 C21H20O10
MW 432.38
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness 1.93

Activity Summary

IC50 14 meas. best 5.31
EC50 5 meas. best 4.91
Kd 2 meas. best 7.12
Ki 1 meas. best 4.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Kd 7.12 7.12 76.2 1
Tumor necrosis factor
CHEMBL1825
 Kd 6.7 6.7 200.0 1
Leishmania donovani
CHEMBL367
 IC50 5.31 5.31 4860.0 1
Solute carrier organic anion transporter family member 2B1
CHEMBL1743124
 IC50 4.98 4.98 10471.3 2
H9c2
CHEMBL614576
 EC50 4.91 4.91 12300.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 4.88 4.88 13090.0 1
Radical scavenging activity
CHEMBL613712
 EC50 4.69 4.69 20370.0 1
Sialidase
CHEMBL5189
 IC50 4.41 4.41 39300.0 1
Neuraminidase
CHEMBL6135
 IC50 4.33 4.33 46900.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 4.28 4.28 52500.0 1
RAW264.7
CHEMBL612557
 IC50 4.27 4.27 53700.0 1
Neuraminidase
CHEMBL6135
 Ki 4.27 4.27 53800.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 4.21 4.21 61000.0 1
Trypanosoma cruzi
CHEMBL368
 IC50 4.16 4.16 69380.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.05 4.05 88400.0 1
HepG2
CHEMBL395
 IC50 4.04 4.04 90600.0 1
Dihydroorotate dehydrogenase (fumarate)
CHEMBL4295843
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Kd = 76.2 nM 7.12 Binding affinity to Bcl-xL (unknown origin) 24974349
Tumor necrosis factor Kd = 200.0 nM 6.7 Binding affinity to TNF-alpha (unknown origin) 24974349
Leishmania donovani IC50 = 4860.0 nM 5.31 Antileishmanial activity against Leishmania donovani MHOM/ET/67/L82 amastigotes ... 30145372
Solute carrier organic anion transporter family member 2B1 IC50 = 10500.0 nM 4.98 Inhibition of human OATP2B1 expressed in Flp-In-CHO cells assessed as inhibition... 37252098
Solute carrier organic anion transporter family member 2B1 IC50 = 10471.29 nM 4.98 Inhibition of human OATP2B1 expressed in Flp-In-CHO cells assessed as inhibition... 37252098
H9c2 EC50 = 12300.0 nM 4.91 Cytoprotective activity against doxorubicin-induced cytotoxicity in rat H9c2 cel... 20932762
NON-PROTEIN TARGET EC50 = 13090.0 nM 4.88 Antioxidant activity assessed as ABTS radical scavenging activity 20932762
Radical scavenging activity EC50 = 20370.0 nM 4.69 Antioxidant activity of the compound assessed as DPPH radical scavenging activit... 20932762
Sialidase IC50 = 39300.0 nM 4.41 Inhibition of Clostridium perfringens neuraminidase 19729316
Neuraminidase IC50 = 46900.0 nM 4.33 Noncompetitive inhibition of recombinant influenza A virus rvH1N1 A/Bervig_Missi... 19729316
Trypanosoma brucei rhodesiense IC50 = 52500.0 nM 4.28 Antitrypanosomal activity against Trypanosoma brucei rhodesiense STIB 900 trypom... 30145372
RAW264.7 IC50 = 53700.0 nM 4.27 Inhibition of LPS induced NO production in mouse RAW264.7 cells measured after 2... 33667099
Neuraminidase Ki = 53800.0 nM 4.27 Noncompetitive inhibition of recombinant influenza A virus rvH1N1 A/Bervig_Missi... 19729316
Human immunodeficiency virus 1 EC50 = 61000.0 nM 4.21 Antiviral activity against HIV1 3B infected in human H9 cells assessed as inhibi... 8158164
Trypanosoma cruzi IC50 = 69380.0 nM 4.16 Antitrypanosomal activity against Trypanosoma cruzi Tulahuen C2C4 trypomastigote... 30145372
NON-PROTEIN TARGET IC50 = 88400.0 nM 4.05 Antioxidant activity assessed as inhibition of AAPH-induced hemolysis in rat RBC... 12828473
HepG2 IC50 = 90600.0 nM 4.04 Anticancer activity against human HepG2 cells assessed as cell viability after 2... 24974349
Dihydroorotate dehydrogenase (fumarate) IC50 = 100000.0 nM 4.0 Inhibition of recombinant oligo-histidine-tagged Leishmania major DHODH expresse... 30145372

Literature References

PubMed DOI Target Context # Activities
19943620 10.1021/np9006298 MCF7 5
19943620 10.1021/np9006298 T47D 4
37252098 10.1039/d3md00078h Solute carrier organic anion transporter family member 2B1 4
37099836 10.1016/j.ejmech.2023.115391 HepG2 3
30145372 10.1016/j.ejmech.2018.08.033 Dihydroorotate dehydrogenase (fumarate) 3
25497988 10.1016/j.bmcl.2014.11.054 RAW264.7 3
20932762 10.1016/j.bmcl.2010.09.086 NON-PROTEIN TARGET 2
- 10.1016/0960-894X(94)80015-4 H9 2
21354800 10.1016/j.bmc.2010.12.043 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
19944611 10.1016/j.bmc.2009.11.015 No relevant target 2
22901896 10.1016/j.bmcl.2012.07.089 Pyricularia grisea 2
19729316 10.1016/j.bmc.2009.08.036 Neuraminidase 2
33667099 10.1021/acs.jnatprod.0c01121 RAW264.7 2
22901896 10.1016/j.bmcl.2012.07.089 Thielaviopsis paradoxa 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
7775983 10.1021/np50117a005 Unchecked 2
22901896 10.1016/j.bmcl.2012.07.089 Alternaria mali 2
22901896 10.1016/j.bmcl.2012.07.089 Athelia rolfsii 2
28248102 10.1021/acs.jnatprod.6b01026 SH-SY5Y 2
37099836 10.1016/j.ejmech.2023.115391 Pancreatic triacylglycerol lipase 2

Data from ChEMBL 36 via Core Engine