Natural Product (NP) Details

General Information of the NP (ID: NP4582)
Name
Glycyrrhetinic acid
Synonyms
enoxolone; 471-53-4; Glycyrrhetic acid; GLYCYRRHETINIC ACID; Uralenic acid; 18-beta-Glycyrrhetinic acid; 18beta-Glycyrrhetinic acid; Rhetinic Acid; Glycyrrhetin; Biosone; Arthrodont; alpha-Glycyrrhetinic acid; 3beta-Hydroxy-11-oxoolean-12-en-30-oic acid; UNII-P540XA09DR; 18beta-Glycyrrhetic acid; MFCD00003706; 3-Glycyrrhetinic acid; MLS000028748; CHEMBL230006; P540XA09DR; Enoxolone (Glycyrrhetinic acid); (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid; (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid; CHEBI:30853; Jintan; Glycyrrhetinate; NSC-35347; NCGC00017244-03; SMR000058239; DSSTox_CID_669; NSC 35347; Glycyrrhetinic acid (JAN); Glycyrrhetinic acid [JAN]; DSSTox_RID_75722; DSSTox_GSID_20669; Enoxolonum; Enoxolona; (3beta,5beta,14beta)-3-Hydroxy-11-Oxoolean-12-En-29-Oic Acid; Enoxolonum [INN-Latin]; 18-beta-Glycyrrhetinic acid, 98+%; Enoxolona [INN-Spanish]; 18-beta-Glycyrrhetic acid; Enoxolone [INN:BAN:DCF]; (5S,8S,15S,18S,1R,2R,10R,14R,20R)-18-hydroxy-1,2,5,8,15,19,19-heptamethyl-13-o xopentacyclo[12.8.0.0<2,11>.0<5,10>.0<15,20>]docos-11-ene-8-carboxylic acid; CAS-471-53-4; CCRIS 3962; SR-01000721867; 1449-05-4; EINECS 207-444-6; BRN 2229654; Enoloxone; NSC-35350; Hidermart (TN); 3-beta-Hydroxy-11-oxoolean-12-en-30-oic acid; Enoxolone (INN); NCGC00181115-01; glycyrrhetinic acids; CBW; (3beta)-3-hydroxy-11-oxoolean-12-en-30-oic acid; Enoxolone (Glycyrrhetin); Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3beta,20beta)-; Opera_ID_1048; SCHEMBL18540; 18 beta-Glycyrrhetintic Acid; 4-10-00-03775 (Beilstein Handbook Reference); MLS001146949; MLS002207101; Enoxolone, Glycyrrhetinic acid; Olean-12-en-30-oic acid, 3-beta-hydroxy-11-oxo-; BX-1; DTXSID9020669; GTPL11264; STX-352; CHEBI: 30853; (3beta,20beta)-3-Hydroxy-11-oxo-olean-12-en-29-oic acid; 18beta-Glycyrrhetinic acid, 97%; HMS2233P23; HY-N0180; Tox21_110804; Tox21_112726; Tox21_200799; BDBM50233538; s2296; SBB006496; ZINC19203131; AKOS015960428; AKOS016036757; HMDB: 0011628; AC-1925; AC-8906; CCG-208506; CS-W020624; DB13089; GM-1658; KS-1262; LMPR0106150014; MCULE-4676598997; Enoxolone 100 microg/mL in Acetonitrile; NCGC00017244-04; NCGC00017244-06; NCGC00142473-03; NCGC00258353-01; 107420-91-7; ST056310; G0149; 3beta-hydroxy-11-oxoolean-12-en-29-oic acid; C02283; D00156; S00284; Enoxolone (synonym: 18ss--Glycyrrhetinic acid); 130100-EP2269977A2; 130100-EP2295411A1; 471G534; A827163; (3?)-3-Hydroxy-11-oxoolean-12-en-30-oic acid; 18beta-Glycyrrhetinic acid, purum, >=97.0% (T); Q-201057; Q5948038; SR-01000721867-3; SR-01000721867-4; SR-01000721867-5; SR-01000721867-6; BRD-K96137854-001-17-1; 3ss-Hydroxy-11-oxo-18ss,20ss-olean-12-en-29-oic acid; Enoxolone, European Pharmacopoeia (EP) Reference Standard; Olean-12-en-30-oic acid, 3beta-hydroxy-11-oxo- (8CI); 3??-Hydroxy-11-oxo-18??,20??-olean-12-en-29-oic acid; 3beta-Hydroxy-11-oxo-18beta,20beta-olean-12-en-29-oic acid; (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-2,4a,6a,6b,9,9,12a-heptamethyl-10-oxidanyl-13-oxidanylidene-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid; Enoxolone; 18beta-Glycyrrhetinic acid; 3?-Hydroxy-11-oxo-18?,20?-olean-12-en-29-oic 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 Prostate cancer [ICD-11: 2C82] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C30H46O4
PubChem CID
10114
Canonical SMILES
CC1(C2CCC3(C(C2(CCC1O)C)C(=O)C=C4C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C
InChI
1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1
InChIKey
MPDGHEJMBKOTSU-YKLVYJNSSA-N
CAS Number
CAS 471-53-4
ChEBI ID
CHEBI:30853
Herb ID
HBIN028184
SymMap ID
SMIT01696
TTD Drug ID
D0X2OD
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Doxorubicin      Solid tumour/cancer     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
                    In-vitro Model Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
                    In-vivo Model Nude mice were subcutaneously inoculated with HepG2 cells at a density of 5 * 106 cells/mouse.
                    Experimental
                    Result(s)		 DOX/PEG-Fmoc-GA containing micelles facilitated the efficient cleavage of GA in tumor tissues/cells, leading to a higher level of synergistic antitumor activity with DOX in vitro and in vivo.
Target and Pathway
Target(s) PTPN1 messenger RNA (PTPN1)  Molecule Info  [3]
KEGG Pathway Adherens junction Click to Show/Hide
2 Insulin signaling pathway
NetPath Pathway FSH Signaling Pathway Click to Show/Hide
Panther Pathway Cadherin signaling pathway Click to Show/Hide
Pathway Interaction Database Insulin Pathway Click to Show/Hide
2 Signaling events mediated by Hepatocyte Growth Factor Receptor (c-Met)
3 Signaling events mediated by PTP1B
4 Calcineurin-regulated NFAT-dependent transcription in lymphocytes
5 Signaling events mediated by TCPTP
6 IGF1 pathway
7 EGF receptor (ErbB1) signaling pathway
8 Posttranslational regulation of adherens junction stability and dissassembly
9 PDGFR-beta signaling pathway
10 N-cadherin signaling events
Reactome Integrin alphaIIb beta3 signaling Click to Show/Hide
2 Regulation of IFNG signaling
3 Regulation of IFNA signaling
4 Growth hormone receptor signaling
WikiPathways Insulin Signaling Click to Show/Hide
2 Growth hormone receptor signaling
3 Leptin signaling pathway
4 Interferon gamma signaling
5 Interferon alpha/beta signaling
6 Integrin alphaIIb beta3 signaling
References
Reference 1 18Alpha-glycyrrhetinic acid targets prostate cancer cells by down-regulating inflammation-related genes. Int J Oncol. 2011 Sep;39(3):635-40.
Reference 2 Glycyrrhetinic acid-conjugated polymeric prodrug micelles co-delivered with doxorubicin as combination therapy treatment for liver cancer. Colloids Surf B Biointerfaces. 2019 Mar 1;175:106-115.
Reference 3 Protein tyrosine phosphatase 1B inhibitory activity of triterpenes isolated from Astilbe koreana. Bioorg Med Chem Lett. 2006 Jun 15;16(12):3273-6.
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