18?-Glycyrrhetic acid

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H46O4
Molecular Weight	470.6838
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]3(C)[C@@H]2C(=O)C=C4[C@H]5C[C@](C)(CC[C@]5(C)CC[C@@]34C)C(O)=O

InChI

InChIKey=MPDGHEJMBKOTSU-PMTKVOBESA-N

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-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C30H46O4
Molecular Weight	470.6838
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27376261
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19429429 | https://www.ncbi.nlm.nih.gov/pubmed/27520483

18alpha-Glycyrrhetinic acid (18-GA), a derivative of enoxolone, is used to inhibit gap junctions and furthermore, it has anti-proliferative properties against various cancer types by affecting the cell cycle proteins. 18alpha-Glycyrrhetinic acid, is a non-selective inhibitor of 11beta-hydroxysteroid dehydrogenases isozymes and results in increased whole body insulin sensitivity and decreased glucose production.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
11-beta-hydroxysteroid dehydrogenase 1 6 Target ID: CHEMBL2391 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19429429	Inhibitor 8504		779.0 nM [IC50]
11-beta-hydroxysteroid dehydrogenase 2 3 Target ID: CHEMBL2908 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19429429	Inhibitor 8504		257.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Leukemia 72 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27376261	Primary		Basic research	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
103.89 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18452416	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		ENOXOLONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1396.97 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18452416	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		ENOXOLONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
9.46 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18452416	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		ENOXOLONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
1500 mg single, oral Highest studied dose Dose: 1500 mg Route: oral Route: single Dose: 1500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8126129	healthy, 29 years Health Status: healthy Age Group: 29 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/8126129	Sources: https://pubmed.ncbi.nlm.nih.gov/8126129

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 MRP1 116 UGT1A3 89	CYP2C19 1119 CYP1A2 1197 CYP2E1 729 P-gp 2052 MRP1 113 UGT1A1 479 UGT1A3 470 UGT2B4 278 UGT2B7 456 UGT1A4 399 UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A9 423 UGT1A10 331 UGT2B15 236 UGT2B17 237

Drug as perpetrator

Target	Modality	Activity
MRP1 232	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/	likely
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/	likely
UGT1A3 99	inhibitor 4027 Sources: https://static-content.springer.com/esm/art%3A10.1038%2Fsrep09627/MediaObjects/41598_2015_BFsrep09627_MOESM1_ESM.pdf Page: 8.0	yes [IC50 6.12 uM]

Drug as victim

Target	Modality	Activity
MRP1 113	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/ Page: 6.0	likely
CYP3A4 1946	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.2012.01516.x Page: 1.0	major
UGT1A3 470	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	major
CYP2C19 1119	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.2012.01516.x Page: 1.0	minor
CYP2C9 1193	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.2012.01516.x Page: 1.0	minor
CYP1A2 1197	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.2012.01516.x Page: 1.0	no
CYP2D6 1388	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.2012.01516.x Page: 1.0	no
CYP2E1 729	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.2012.01516.x Page: 1.0	no
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/ Page: 6.0	no
UGT1A10 331	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT1A4 399	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT1A6 343	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT1A7 249	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT1A8 323	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT1A9 423	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT2B15 236	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT2B17 237	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT1A1 479	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	yes
UGT2B4 278	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	yes
UGT2B7 456	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	yes

Sourcing

Vendor/Aggregator	ID	URL
abcr GmbH	AB136427	http://www.abcr.com/shop/en/AB136427
Achemtek	0104-020457	http://www.achemtek.com/471-53-4
Acorn PharmaTech	ACN-036282	http://www.acornpharmatech.com/
Acros Organics	AC120150050	https://www.fishersci.com/shop/products/18-glycyrrhetinic-acid-98-acros-organics/AC120150050
Acros Organics	AC120150250	https://www.fishersci.com/shop/products/18-glycyrrhetinic-acid-98-acros-organics/AC120150250
AEchem Scientific Corp., USA	AE1-006547	http://www.aechemsc.com/info_products/AE1-006547.php
Aurora Fine Chemicals LLC	A13.139.522	http://online.aurorafinechemicals.com/info?ID=A13.139.522
AvaChem Scientific	1106	http://www.avachem.com/productSearch.asp?1106
Avantor Inc	101179-654	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101179-654
Avantor Inc	200015-658	https://us.vwr.com/store/product/18599070/18-beta-glycyrrhetinic-acid-98
Avantor Inc	700006-634	https://us.vwr.com/store/product/21572407/glycyrrhetic-acid-98
Avantor Inc	700006-636	https://us.vwr.com/store/product/21572407/glycyrrhetic-acid-98
BioSynth	Q-201057	https://www.biosynth.com/en/products/chemical-intermediates/advanced-intermediates/products/Q-201057.html
Boerchem	BC201656	http://www.boerchem.com/?product_33783.html
Chem Scene	CS-W020624	http://www.chemscene.com/471-53-4.html
ChemFaces	CFN99152	http://www.chemfaces.com/natural/Glycyrrhetinic-acid-CFN99152.html
ChemMol	30100980	http://www.chemmol.com/chemmol/30100980.html
ChemMol	30114287	http://www.chemmol.com/chemmol/30114287.html
ChemMol	44000914	http://www.chemmol.com/chemmol/44000914.html
ChemMol	99088065	http://www.chemmol.com/chemmol/99088065.html
Chemspace	CSSB00020617985	https://chem-space.com/CSSB00020617985
China MainChem Co., Ltd	471-53-4	https://www.mainchem.com/product/china-enoxolone-cas-471-53-4-glycyrrhetinic-acid-supplier/
DC Chemicals	DCG-032	http://www.dcchemicals.com//product_show-18_beta_Glycyrrhetintic_Acid.html
eNovation Chemicals	D676398	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676398
eNovation Chemicals	D765568	https://www.enovationchem.com/ProductDetails.asp?ProductID=D765568
Glentham Life Sciences	GP8041	http://www.glentham.com/products/product/GP8041/
Hairui	HR135798	http://www.hairuichem.com/en/product/471-53-4.html
Herbest Bio-Tech	HH231694	http://www.bjherbest.com/analytical-standard/saponins/18-beta-glycyrrhetinic-acid-471-53-4.html
Lab Network	LN00839314	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00839314
LGC Standards	DRE-A13167700AL-100	https://www.lgcstandards.com/US/en/p/DRE-A13167700AL-100
LGC Standards	DRE-C13167700	https://www.lgcstandards.com/US/en/p/DRE-C13167700
LGC Standards	MM3399.00	https://www.lgcstandards.com/US/en/p/MM3399.00
mcule	MCULE-4676598997	https://mcule.com/MCULE-4676598997/
MedChem Express	HY-N0180	https://www.medchemexpress.com/18_beta_-Glycyrrhetinic_acid.html
MuseChem	R048750	https://www.musechem.com/product/R048750.html
Oakwood	103973	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=194966&ExtHyperLink=1
OChem	3435	http://www.ocheminc.com/index.php?act=psearch&pid=471G534
R&D Chemicals	43	http://www.rdchemicals.com/chemicals.php?mode=details&mol_id=7860
Sigma-Aldrich	50510_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/50510?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	E0180500_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/e0180500?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	G10105_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/g10105?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S527188	http://www.smolecule.com/products/s527188
TCI (Tokyo Chemical Industry)	G0149	http://www.tcichemicals.com/eshop/en/us/commodity/G0149/index.html
THE BioTek	bt-267335	https://www.thebiotek.com/product/inhibitors/bt-267335
VladaChem	VL277837-1G	https://www.vladachem.com/product.php?products=471-53-4
Yuhao Chemical	JZ1453	http://www.chemyuhao.com/471-53-4.html

PubMed

Title	Date	PubMed
18α-Glycyrrhetinic acid lethality for neuroblastoma cells via de-regulating the Beclin-1/Bcl-2 complex and inducing apoptosis.	2016-10-01	27520483

Patents

Sample Use Guides

In Vivo Use Guide

Male Sprague-Dawley rats were randomly divided into four groups: control, liver fibrosis, 12.5 mg/kg 18alpha-Glycyrrhetinic acid and 25 mg/kg 18alpha-Glycyrrhetinic acid group. In liver fibrosis group, animals were intraperitoneally treated with normal saline (NS). In 12.5 mg/kg 18alpha-Glycyrrhetinic acid group and 25 mg/kg 18alpha-Glycyrrhetinic acid group, animals were intraperitoneally treated with 18alpha-Glycyrrhetinic acid at 25 and 12.5 mg/kg, respectively, once daily for 8 weeks.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Human SH-SY5Y, SK-N-MC and SK-N-SH neuroblastoma cells were treated with 18-Glycyrrhetinic acid (30 mkM) for 24 h. The cells were incubated with 5 lM acridine orange (AO) for 20 min in the dark and dye fluorescence intensity was determined by flow cytometry.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 15:45:01 GMT 2025` Edited by `admin` on `Wed Apr 02 15:45:01 GMT 2025`
Record UNII	X6NYL2CP2E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

18-Isoglycyrrhetinic acid

Preferred Name

English

18?-Glycyrrhetic acid

Common Name

English

18?-Olean-12-en-30-oic acid, 3?-hydroxy-11-oxo-

Systematic Name

English

(3?,18?,20?)-3-Hydroxy-11-oxoolean-12-en-29-oic acid

Systematic Name

English

18?-Glycyrrhetinic acid

Common Name

English

Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3?,18?,20?)-

Systematic Name

English

?-Glycyrrhetinic acid

Common Name

English

3?-hydroxy-11-oxo-18?-olean-12-en-30-oic acid (18?-glycyrrhetinic acid),

Systematic Name

English

ENOXOLONE IMPURITY A [EP IMPURITY]

Common Name

English

Code System Code Type Description

CAS

1449-05-4

Created by admin on Wed Apr 02 15:45:01 GMT 2025 , Edited by admin on Wed Apr 02 15:45:01 GMT 2025

PRIMARY

FDA UNII

X6NYL2CP2E

Created by admin on Wed Apr 02 15:45:01 GMT 2025 , Edited by admin on Wed Apr 02 15:45:01 GMT 2025

PRIMARY

PUBCHEM

73398

Created by admin on Wed Apr 02 15:45:01 GMT 2025 , Edited by admin on Wed Apr 02 15:45:01 GMT 2025

PRIMARY

EPA CompTox

DTXSID20872408

Created by admin on Wed Apr 02 15:45:01 GMT 2025 , Edited by admin on Wed Apr 02 15:45:01 GMT 2025

PRIMARY

Related Record Type Details


					P540XA09DR

ENOXOLONE

PARENT -> IMPURITY

Amount:

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27376261Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19429429 | https://www.ncbi.nlm.nih.gov/pubmed/27520483

Originator

Approval Year

Targets

Conditions

Approved Use

Cmax

AUC

T1/2

Doses

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27376261
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19429429 | https://www.ncbi.nlm.nih.gov/pubmed/27520483

C_max

T_1/2

Drug as perpetrator