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Compound Detail

CHEMBL441687

GLYCYRRHIZIN
🧪 Phase II
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🧪 Phase II
CC1(C)[C@@H](O[C@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL441687
Name GLYCYRRHIZIN
Phase Phase II
Structure Type MOL
InChI Key LPLVUJXQOOQHMX-QWBHMCJMSA-N

Known Names

.beta.-glycyrrhizin 18.beta.-glycyrrhizic acid E958 Glycyron Glycyrrhizate Glycyrrhizic acid Glycyrrhizin Glycyrrhizinate NSC-167409 NSC-234419 Potenlini
21
Targets
52
Activities
4
Assay Types
0
PK Parameters
20
Publications
11
Known Names
4
Indications

Molecular Properties

822.9
MW (Da)
2.25
ALogP
13
HBA
8
HBD
267.0
PSA (Ų)
0.17
QED
3
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Oligosaccharide
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C42H62O16
MW 822.94
Aromatic Rings 0
Heavy Atoms 58
NP-Likeness 2.52

Indications

Prostatic Neoplasms, Castration-Resistant Renal Insufficiency, Chronic Osteoarthritis Periapical Periodontitis

ATC Classification

A05BA08
glycyrrhizic acid
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: BILE AND LIVER THERAPY

Activity Summary

IC50 32 meas. best 9.4
EC50 11 meas. best 9.0
Ki 5 meas. best 6.08
Kd 4 meas. best 4.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
11-beta-hydroxysteroid dehydrogenase type 2
CHEMBL3746
 IC50 9.4 9.1833 0.4 3
11-beta-hydroxysteroid dehydrogenase type 2
CHEMBL3746
 EC50 9.0 9.0 1.0 1
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL3910
 IC50 8.52 7.9925 3.0 4
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL4235
 IC50 8.22 7.9833 6.0 3
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL3910
 EC50 8.1 8.1 8.0 1
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL4235
 EC50 8.0 8.0 10.0 1
ATP-binding cassette sub-family C member 2
CHEMBL2073676
 Ki 6.08 5.9 840.0 2
SARS-CoV-2
CHEMBL4303835
 EC50 5.58 4.96 2600.0 2
Solute carrier organic anion transporter family member 1B2
CHEMBL1781861
 Ki 5.21 5.21 6100.0 1
dengue virus type 2
CHEMBL613966
 IC50 5.09 5.09 8100.0 1
Unchecked
CHEMBL612545
 IC50 5.07 4.6114 8500.0 7
ADMET
CHEMBL612558
 IC50 5.03 5.03 9300.0 1
Beta-glucuronidase
CHEMBL3217380
 IC50 4.92 4.92 12150.0 1
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
 Ki 4.9 4.9 12500.0 1
MDCK
CHEMBL614068
 EC50 4.82 4.82 15200.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
 Ki 4.8 4.8 15900.0 1
RAW264.7
CHEMBL612557
 IC50 4.68 4.68 20700.0 1
Human gammaherpesvirus 4
CHEMBL613124
 EC50 4.52 4.52 30000.0 1
Influenza A virus
CHEMBL613740
 IC50 4.4 4.4 39600.0 1
Huh-7
CHEMBL614039
 IC50 4.18 4.18 65700.0 1
A549
CHEMBL392
 IC50 4.09 4.09 80300.0 1
Hepatocyte
CHEMBL3140324
 IC50 4.08 4.08 82400.0 1
High mobility group protein B1
CHEMBL2311236
 Kd 4.06 4.06 87000.0 1
Beta-glucuronidase
CHEMBL4814
 IC50 4.01 4.01 97210.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 0.4 nM 9.4 Inhibition of human 11beta-HSD2 expressed in HEK293 cells assessed as conversion... 22360639
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 0.7 nM 9.15 Inhibition of human 11beta-HSD2 expressed in human HEK293 cells assessed as conv... 22148241
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 1.0 nM 9.0 Inhibition of human microsomal 11beta-HSD2 expressed in HEK293 cells assessed as... 19564108
11-beta-hydroxysteroid dehydrogenase type 2 EC50 = 1.0 nM 9.0 Inhibition of human 11beta-HSD2 expressed in HEK293 cells assessed as [3H]cortis... 22440625
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 3.0 nM 8.52 Inhibition of mouse 11beta-HSD1 expressed in HEK293 cells assessed as conversion... 22360639
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 6.0 nM 8.22 Inhibition of human 11beta-HSD1 expressed in HEK293 cells assessed as conversion... 22360639
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 8.0 nM 8.1 Inhibition of mouse microsomal 11beta-HSD1 expressed in HEK293 cells assessed as... 19564108
11-beta-hydroxysteroid dehydrogenase 1 EC50 = 8.0 nM 8.1 Inhibition of mouse 11beta-HSD1 expressed in HEK293 cells assessed as [3H]cortis... 22440625
11-beta-hydroxysteroid dehydrogenase 1 EC50 = 10.0 nM 8.0 Inhibition of human 11beta-HSD1 expressed in HEK293 cells assessed as [3H]cortis... 22440625
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 10.0 nM 8.0 Inhibition of human microsomal 11beta-HSD1 expressed in HEK293 cells assessed as... 19564108
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 15.0 nM 7.82 Inhibition of mouse liver microsome 11betaHSD1 expressed in HEK293 cells assesse... 19574056
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 18.6 nM 7.73 Inhibition of human 11beta-HSD1 expressed in human HEK293 cells assessed as conv... 22148241
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 29.5 nM 7.53 Inhibition of mouse 11beta-HSD1 expressed in human HEK293 cells assessed as conv... 22148241
ATP-binding cassette sub-family C member 2 Ki = 840.0 nM 6.08 TP_TRANSPORTER: inhibition of DNP-SG uptake in bile canalicular membrane vesicle... 15618649
ATP-binding cassette sub-family C member 2 Ki = 1910.0 nM 5.72 TP_TRANSPORTER: inhibition of SN-38 uptake in bile canalicular membrane vesicles... 15618649
SARS-CoV-2 EC50 = 2600.0 nM 5.58 Antiviral activity against luciferase independent SARS CoV-2 spike-pseudotyped l... 38864383
Solute carrier organic anion transporter family member 1B2 Ki = 6100.0 nM 5.21 TP_TRANSPORTER: inhibition of E1S uptake in Xenopus laevis oocytes 12963436
dengue virus type 2 IC50 = 8100.0 nM 5.09 Antiviral activity against DENV2 16681 infected in African green monkey Vero E6 ... 31519375
Unchecked IC50 = 8500.0 nM 5.07 Inhibition of hyaluronidase (unknown origin) using hyaluronic acid as substrate ... 28202328
Unchecked IC50 = 8500.0 nM 5.07 Inhibition of bovine testis hyaluronidase using hyaluronic acid as substrate pre... 27165854

Literature References

PubMed DOI Target Context # Activities
30288224 10.1039/C8MD00288F Mus musculus 38
11325227 10.1021/np000393f Hepatocyte 10
27165854 10.1016/j.bmcl.2016.04.082 Unchecked 7
37542990 10.1016/j.ejmech.2023.115696 Mus musculus 7
29224994 10.1016/j.bmc.2017.11.046 Mus musculus 7
6677713 10.1021/np50030a003 Hepatocyte 6
16441065 10.1021/np058080d Unchecked 6
19131254 10.1016/j.bmc.2008.11.077 Mus musculus 6
17685651 10.1021/np068075p Unchecked 5
31519375 10.1016/j.bmcl.2019.126645 dengue virus type 2 5
19131254 10.1016/j.bmc.2008.11.077 Unchecked 5
23454223 10.1016/j.bmc.2013.01.061 ECV-304 5
38864383 10.1021/acs.jmedchem.4c00597 SARS-CoV-2 4
24084294 10.1016/j.bmc.2013.09.008 ECV-304 4
19131254 10.1016/j.bmc.2008.11.077 Raji 4
17663539 10.1021/jm070295s SARS-CoV 4
38864383 10.1021/acs.jmedchem.4c00597 No relevant target 3
31814955 10.1039/C9MD00345B Mus musculus 3
29353722 10.1016/j.ejmech.2018.01.011 Hepatocyte 3
38864383 10.1021/acs.jmedchem.4c00597 Unchecked 3

Data from ChEMBL 36 via Core Engine