GLYCYRRHIZIN

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Synonyms
Status
Molecule Category UNKNOWN
UNII 6FO62043WK
EPA CompTox DTXSID8047006

Structure

InChI Key LPLVUJXQOOQHMX-QWBHMCJMSA-N
Smiles 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
InChI
InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C42H62O16
Molecular Weight 822.94
AlogP 2.25
Hydrogen Bond Acceptor 13.0
Hydrogen Bond Donor 8.0
Number of Rotational Bond 7.0
Polar Surface Area 267.04
Molecular species ACID
Aromatic Rings 0.0
Heavy Atoms 58.0
Assay Description Organism Bioactivity Reference
Inhibition of TPA-induced Epstein-Barr virus early antigen in Raji cells at 1000 mol ratio/TPA relative to control Human herpesvirus 4 27.4 %
Inhibition of TPA-induced Epstein-Barr virus early antigen in Raji cells at 500 mol ratio/TPA relative to control Human herpesvirus 4 63.3 %
Inhibition of TPA-induced Epstein-Barr virus early antigen in Raji cells at 100 mol ratio/TPA relative to control Human herpesvirus 4 83.3 %
Inhibition of TPA-induced Epstein-Barr virus early antigen in Raji cells at 10 mol ratio/TPA relative to control Human herpesvirus 4 100.0 %
Hepatoprotective activity in mouse hepatocytes assessed inhibition of D-galactosamine/TNFalpha-induced cell death at 100 uM administered before 30 mins of TNFalpha challenge measured after 18 hrs Mus musculus 11.1 %
Hepatoprotective activity in mouse hepatocytes assessed inhibition of D-galactosamine/TNFalpha-induced cell death at 200 uM administered before 30 mins of TNFalpha challenge measured after 18 hrs Mus musculus 20.3 %
Hepatoprotective activity in mouse hepatocytes assessed inhibition of D-galactosamine/TNFalpha-induced cell death at 50 uM administered before 30 mins of TNFalpha challenge measured after 18 hrs Mus musculus 11.0 %
Inhibition of TPA-induced EBV-early antigen activation in human Raji cells Human herpesvirus 4 572.0 molar ratio
Inhibition of mouse liver microsome 11betaHSD1 expressed in HEK293 cells assessed as conversion of [3H]cortisone into [3H]cortisol by scintillation proximity assay Mus musculus 15.0 nM
Inhibition of human microsomal 11beta-HSD1 expressed in HEK293 cells assessed as conversion of [3H]cortisone to [3H]cortisol by scintillation proximity assay Homo sapiens 10.0 nM
Inhibition of mouse microsomal 11beta-HSD1 expressed in HEK293 cells assessed as conversion of [3H]cortisone to [3H]cortisol by scintillation proximity assay Mus musculus 8.0 nM
Inhibition of human microsomal 11beta-HSD2 expressed in HEK293 cells assessed as conversion of [3H]cortisone to [3H]cortisol by scintillation proximity assay Homo sapiens 1.0 nM
Inhibition of human recombinant 11beta-HSD1 expressed in HEK293 cells assessed as conversion of [1,2-3H]cortisone to cortisol at 1 uM after 10 mins by scintillation counting Homo sapiens 63.2 %
Inhibition of human recombinant 11beta-HSD2 expressed in HEK293 cells assessed as oxidation of [1,2,6,7-3H]cortisol to cortisone at 1 uM after 10 mins by scintillation counting Homo sapiens 28.1 %
Inhibition of human 11beta-HSD1 expressed in human HEK293 cells assessed as conversion of [3H]cortisone to [3H]cortisol by scintillation proximity assay Homo sapiens 18.6 nM
Inhibition of mouse 11beta-HSD1 expressed in human HEK293 cells assessed as conversion of [3H]cortisone to [3H]cortisol by scintillation proximity assay Mus musculus 29.5 nM
Inhibition of human 11beta-HSD2 expressed in human HEK293 cells assessed as conversion of [3H]cortisone to [3H]cortisol by scintillation proximity assay Homo sapiens 0.7 nM
Inhibition of human 11beta-HSD1 expressed in HEK293 cells assessed as [3H]cortisol production after 60 mins by SPA Homo sapiens 10.0 nM
Inhibition of mouse 11beta-HSD1 expressed in HEK293 cells assessed as [3H]cortisol production after 60 mins by SPA Mus musculus 8.0 nM
Inhibition of human 11beta-HSD2 expressed in HEK293 cells assessed as [3H]cortisol production after 60 mins by SPA Homo sapiens 1.0 nM
Inhibition of human 11beta-HSD1 expressed in HEK293 cells assessed as conversion of [3H]cortisone into [3H]cortisol by scintillation proximity assay Homo sapiens 6.0 nM
Inhibition of mouse 11beta-HSD1 expressed in HEK293 cells assessed as conversion of [3H]cortisone into [3H]cortisol by scintillation proximity assay Mus musculus 3.0 nM
Inhibition of human 11beta-HSD2 expressed in HEK293 cells assessed as conversion of [3H]cortisone into [3H]cortisol by scintillation proximity assay Homo sapiens 0.4 nM
TP_TRANSPORTER: inhibition of DNP-SG uptake in bile canalicular membrane vesicles from SD rat Rattus norvegicus 840.0 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 65.8 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 90.9 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 28.7 %
Inhibition of recombinant human CYP1A1 expressed in yeast microsomal membranes at 10 uM by fluorescence assay relative to control Homo sapiens 39.0 %
Inhibition of human CYP1B1 expressed in yeast microsomal membranes at 10 uM using 7-ethoxyresorufin as substrate by fluorescence assay relative to control Homo sapiens 10.5 %
Antiinflammatory activity against TPA-induced ear edema in BALB/c mouse assessed as inhibition of ear edema at 50 mg/kg, po administered 6 mins prior to TPA challenge and treated twice in 4 hrs and measured after 6 hrs post administration relative to control Mus musculus -5.41 %
Antiinflammatory activity against TPA-induced ear edema in BALB/c mouse assessed as inhibition of ear edema at 100 mg/kg, po administered 6 mins prior to TPA challenge and treated twice in 4 hrs and measured after 6 hrs post administration relative to control Mus musculus -10.81 %
Antiviral activity against DENV2 16681 infected in African green monkey Vero E6 cells assessed as inhibitory rate of NS4B positive cells at 10 uM measured after 96 hrs incubation by DAPI staining based immunofluorescence method Dengue virus 2 70.5 %

Related Entries

Cross References

Resources Reference
ChEBI 15939
ChEMBL CHEMBL441687
DrugBank DB13751
DrugCentral 1325
FDA SRS 6FO62043WK
Guide to Pharmacology 4688
PubChem 14982
SureChEMBL SCHEMBL17684
ZINC ZINC000096015174
CONTENTS