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Compound Detail

CHEMBL233930

ASTRAGALIN
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O=c1c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(-c2ccc(O)cc2)oc2cc(O)cc(O)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL233930
Name ASTRAGALIN
Phase Preclinical
Structure Type MOL
InChI Key JPUKWEQWGBDDQB-QSOFNFLRSA-N
16
Targets
27
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)
0.28
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 2.07

Activity Summary

IC50 19 meas. best 5.51
Ki 5 meas. best 8.31
EC50 3 meas. best 4.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 12
CHEMBL3242
 Ki 8.31 8.31 4.9 1
Carbonic anhydrase 2
CHEMBL205
 Ki 6.78 6.78 168.0 1
Carbonic anhydrase 7
CHEMBL2326
 Ki 6.37 6.37 423.7 1
U-87 MG
CHEMBL614247
 IC50 5.51 5.51 3120.0 1
SW-620
CHEMBL612262
 IC50 5.34 5.34 4600.0 1
Aldo-keto reductase family 1 member B1
CHEMBL2622
 IC50 5.29 5.29 5090.0 1
Carbonic anhydrase 4
CHEMBL3729
 Ki 5.25 5.25 5591.2 1
Trypanosoma cruzi
CHEMBL368
 IC50 4.8 4.8 15700.0 1
HCT-15
CHEMBL612263
 IC50 4.63 4.63 23500.0 1
BV-2
CHEMBL614781
 IC50 4.63 4.37 23500.0 2
Sialidase
CHEMBL5189
 IC50 4.53 4.53 29400.0 1
Neuraminidase
CHEMBL6135
 Ki 4.48 4.48 33000.0 1
RAW264.7
CHEMBL612557
 IC50 4.43 4.295 37100.0 4
Neuraminidase
CHEMBL6135
 IC50 4.42 4.42 38400.0 1
U-251
CHEMBL615022
 IC50 4.42 4.42 37600.0 1
Influenza A virus
CHEMBL613740
 EC50 4.4 4.305 40000.0 2
Aldo-keto reductase family 1 member B1
CHEMBL1900
 IC50 4.22 4.22 60500.0 1
Neuraminidase
CHEMBL6135
 EC50 4.14 4.14 72800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 12 Ki = 4.9 nM 8.31 Inhibition of human recombinant carbonic anhydrase 12 preincubated for 15 mins a... 26498393
Carbonic anhydrase 2 Ki = 168.0 nM 6.78 Inhibition of human recombinant carbonic anhydrase 2 preincubated for 15 mins at... 26498393
Carbonic anhydrase 7 Ki = 423.7 nM 6.37 Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins at... 26498393
U-87 MG IC50 = 3120.0 nM 5.51 Antiproliferative activity against human U87MG cells after 72 hrs by sulforhodam... 25981689
SW-620 IC50 = 4600.0 nM 5.34 Antiproliferative activity against human SW620 cells after 72 hrs by sulforhodam... 25981689
Aldo-keto reductase family 1 member B1 IC50 = 5090.0 nM 5.29 Inhibition of rat lens aldose reductase 18298080
Carbonic anhydrase 4 Ki = 5591.2 nM 5.25 Inhibition of human recombinant carbonic anhydrase 4 preincubated for 15 mins at... 26498393
Trypanosoma cruzi IC50 = 15700.0 nM 4.8 Antitrypanosomal activity against epimastigote form of Trypanosoma cruzi assesse... 21466157
HCT-15 IC50 = 23500.0 nM 4.63 Antiproliferative activity against human HCT15 cells after 72 hrs by sulforhodam... 25981689
BV-2 IC50 = 23500.0 nM 4.63 Antiinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induc... 28165740
Sialidase IC50 = 29400.0 nM 4.53 Inhibition of Clostridium perfringens neuraminidase 19729316
Neuraminidase Ki = 33000.0 nM 4.48 Noncompetitive inhibition of recombinant influenza A virus rvH1N1 A/Bervig_Missi... 19729316
RAW264.7 IC50 = 37100.0 nM 4.43 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 24679441
Neuraminidase IC50 = 38400.0 nM 4.42 Noncompetitive inhibition of recombinant influenza A virus rvH1N1 A/Bervig_Missi... 19729316
U-251 IC50 = 37600.0 nM 4.42 Antiproliferative activity against human U251 cells after 72 hrs by sulforhodami... 25981689
Influenza A virus EC50 = 40000.0 nM 4.4 Antiviral activity against influenza A virus H1N1 A/PR/8/34 infected in MDCK cel... 19729316
RAW264.7 IC50 = 40600.0 nM 4.39 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 24679441
Aldo-keto reductase family 1 member B1 IC50 = 60500.0 nM 4.22 Inhibition of human recombinant aldose reductase using D-glyceraldehyde as subst... 22261024
Influenza A virus EC50 = 61900.0 nM 4.21 Antiviral activity against influenza A virus H9N2 A/Chicken/Korea/MS96/96 infect... 19729316
RAW264.7 IC50 = 64000.0 nM 4.19 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 21353543

Literature References

PubMed DOI Target Context # Activities
17400451 10.1016/j.bmcl.2007.03.051 Mus musculus 11
21466157 10.1021/np1008043 Trypanosoma cruzi 11
3430165 10.1021/np50052a017 Angiotensin-converting enzyme 8
24679441 10.1016/j.bmcl.2014.03.014 RAW264.7 7
28479197 10.1016/j.bmcl.2017.04.076 Thoracic aorta 7
21353543 10.1016/j.bmcl.2011.01.066 RAW264.7 5
21493073 10.1016/j.bmc.2011.03.040 3T3-L1 4
28479197 10.1016/j.bmcl.2017.04.076 Unchecked 3
15104496 10.1021/np030470h Human respirovirus 3 2
- 10.1016/0960-894X(94)80015-4 H9 2
34403725 10.1016/j.bmcl.2021.128326 3T3-L1 2
15104496 10.1021/np030470h Influenza A virus 2
19729316 10.1016/j.bmc.2009.08.036 Unchecked 2
7320737 10.1021/np50017a003 P388 2
19729316 10.1016/j.bmc.2009.08.036 Neuraminidase 2
23149227 10.1016/j.bmcl.2012.10.043 BV-2 2
28165740 10.1021/acs.jnatprod.6b00981 C6 2
24679441 10.1016/j.bmcl.2014.03.014 Bifunctional epoxide hydrolase 2 2
24900249 10.1021/ml100171x L6 2
25935644 10.1016/j.bmcl.2015.04.045 Pancreatic triacylglycerol lipase 2

Data from ChEMBL 36 via Core Engine