Natural Product (NP) Details

General Information of the NP (ID: NP4435)
Name
Glycyrrhizin
Synonyms
Glycyrrhizic acid; glycyrrhizin; Glycyrrhizinic acid; 1405-86-3; Glycyrrhetinic acid glycoside; glyzyrrhizin; Glizigen; Glycyron; 18-beta-Glycyrrhizic acid; Liquorice; UNII-6FO62043WK; CHEBI:15939; C42H62O16; CHEMBL441687; NSC 2800; beta-Glycyrrhizin; 6FO62043WK; Rizinsan K2 A2 (free acid); NSC-167409; NSC-234419; DSSTox_CID_27006; DSSTox_RID_82047; DSSTox_GSID_47006; Glycyrrhitin; Dermacrin; Glycyram; (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid; 30-hydroxy-11,30-dioxoolean-12-en-3beta-yl (2-O-beta-D-glucopyranosyluronic acid)-alpha-D-glucopyranosiduronic acid; 18beta-Glycyrrhizic acid; Neo-Umor; CAS-1405-86-3; HSDB 496; alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-; EINECS 215-785-7; NSC 167409; NSC 234419; BRN 0077922; CCRIS 8444; MFCD00065194; NCGC00183128-01; (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxy-tetrahydropyran-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid; Glycyrrhizin, 93%; ammonium-glycyrrhizinate; Glycyrrhizic acid, 2K; beta-Glycyrrhizinic acid; 132215-36-2; Glycyrrhizia uralensis Fisch; SCHEMBL17684; 20beta-Carboxy-11-oxo-30-norolean-12-en-3beta-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid; 4-18-00-05156 (Beilstein Handbook Reference); alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-beta-D-glucopyranuron osyl-; BIDD:ER0363; GTPL4688; DTXSID8047006; Glycyrrhizin (Glycyrrhizic Acid); HY-N0184; Tox21_111520; Tox21_113426; Tox21_303493; BDBM50185127; HMDB:0029843; s2302; ZINC96015174; AKOS015893086; AKOS015969345; CCG-270511; CS-7695; DB13751; GM-1292; NCGC00257455-01; NCGC00386162-01; NCGC00386162-02; (3beta,20beta)-20-Carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-beta-1- 7-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid; (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid; alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-beta-1- 7-glucopyranuronosyl-; AS-13001; E958; G0150; N1792; J10040; AB01566834_01; 405G863; Q418705; Q-201172; BRD-K83486494-318-01-5; Glycyrrhizic acid, United States Pharmacopeia (USP) Reference Standard; xy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid; Glycyrrhizic Acid, Pharmaceutical Secondary Standard; Certified Reference Material; (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carbo; (2S,3S,4S,5R,6S)-6-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid; (3.beta.,20.beta.)-20-Carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-.beta.-1- 7-glucopyranuronosyl-.alpha.-D-glucopyranosiduronic acid
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Species Origin Glycyrrhiza glabra ...     Click to Show/Hide
Glycyrrhiza glabra
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Glycyrrhiza
Species: Glycyrrhiza glabra
Disease Influenza [ICD-11: 1E30] Phase 3 [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -6.305
 
MDCK Permeability
 -5.096
 
PAMPA
 +++
 
HIA
 - - -
 
Distribution
VDss
 -0.507
 
PPB
 85.9%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 +++
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 - - -
 
Excretion
CLplasma
 -0.252
 
T1/2
 5.531
Toxicity
DILI
 +++
 
Rat Oral Acute Toxicity
 - - -
 
FDAMDD
 - -
 
Respiratory
 - -
 
Human Hepatotoxicity
 +
 
Ototoxicity
 +++
 
Drug-induced Nephrotoxicity
 +++
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 - -
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C42H62O16
PubChem CID
14982
Canonical SMILES
CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)C(=O)O)O)O)OC5C(C(C(C(O5)C(=O)O)O)O)O)C)C(=O)C=C6C3(CCC7(C6CC(CC7)(C)C(=O)O)C)C)C)C
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
InChIKey
LPLVUJXQOOQHMX-QWBHMCJMSA-N
CAS Number
CAS 1405-86-3
ChEBI ID
CHEBI:15939
Herb ID
HBIN028191
SymMap ID
SMIT00219
TCMSP ID
MOL004932
TTD Drug ID
D0T8QB
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Methotrexate      Leukaemia     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 Methotrexate and compound glycyrrhizin can be an effective alternative therapy in the treatment of erythrodermic psoriasis with BP.
    β. A List of Drug(s) Whose Resistance can be Reversed by This NP
          lamivudine      Hepatitis virus infection     Click to Show/Hide the Molecular Data of This Drug
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression ABCC2  Molecule Info 
Pathway MAP
Up-regulation Expression ABCC3  Molecule Info 
Pathway MAP
Up-regulation Expression ABCC4  Molecule Info 
Pathway MAP
Up-regulation Expression ABCC5  Molecule Info 
Pathway MAP
                    In-vitro Model Huh-7 CVCL_0336 Adult hepatocellular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 The combination of glycyrrhizin and lamivudine inhibit the cisplatin efflux from the HCC cells, acting as modulators to reverse cisplatin resistance.
Target and Pathway
Target(s) Corticosteroid 11-beta-dehydrogenase 1 (HSD11B1)  Molecule Info  [4]
KEGG Pathway Steroid hormone biosynthesis Click to Show/Hide
2 Metabolism of xenobiotics by cytochrome P450
3 Metabolic pathways
4 Chemical carcinogenesis
NetPath Pathway IL1 Signaling Pathway Click to Show/Hide
2 FSH Signaling Pathway
Pathwhiz Pathway Steroidogenesis Click to Show/Hide
Reactome Glucocorticoid biosynthesis Click to Show/Hide
WikiPathways Prostaglandin Synthesis and Regulation Click to Show/Hide
2 Metabolism of steroid hormones and vitamin D
3 Glucocorticoid & Mineralcorticoid Metabolism
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4688).
Reference 2 Erythrodermic psoriasis with bullous pemphigoid: combination treatment with methotrexate and compound glycyrrhizin. Diagn Pathol. 2014 May 29;9:102.
Reference 3 The combination of glycyrrhizin and lamivudine can reverse the cisplatin resistance in hepatocellular carcinoma cells through inhibition of multidrug resistance-associated proteins. Int J Oncol. 2007 Dec;31(6):1465-72.
Reference 4 Discovery of novel dual functional agent as PPARgamma agonist and 11beta-HSD1 inhibitor for the treatment of diabetes. Bioorg Med Chem. 2009 Aug 1;17(15):5722-32.
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