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Details

Stereochemistry ABSOLUTE
Molecular Formula C42H62O16
Molecular Weight 822.9321
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLYCYRRHIZIN

SMILES

C[C@]12CC[C@@](C)(C[C@H]1C3=CC(=O)[C@@H]4[C@@]5(C)CC[C@H](O[C@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O[C@@H]7O[C@@H]([C@@H](O)[C@H](O)[C@H]7O)C(O)=O)C(O)=O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC2)C(O)=O

InChI

InChIKey=LPLVUJXQOOQHMX-QWBHMCJMSA-N
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

HIDE SMILES / InChI
Molecular Formula C42H62O16
Molecular Weight 822.9321
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 19 / 19
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://en.wikipedia.org/wiki/Enoxolone

Glycyrrhizic Acid is specific compound isolated from licorice plants. Ammonium Glycyrrhizate (also known as GLYCYRRHIZIN, AMMONIATED) is a salt, was investigated to be a safe and is used as ingredient in the formulation of makeup, fragrance, hair care, skin care, shaving, personal hygiene and suntan products.

Approval Year

1921
1468
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
846
Peroxisome proliferator-activated receptor gamma coactivator 1-alpha
17
Target ID: Q9UBK2|||Q3LIG1
Gene ID: 10891.0
Gene Symbol: PPARGC1A
Target Organism: Homo sapiens (Human)
Activator
1447
Alanine aminotransferase 1
17
Target ID: P24298
Gene ID: 2875.0
Gene Symbol: GPT
Target Organism: Homo sapiens (Human)
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Palliative
Approved
8583
Stronger Neo-Minophagen C

Approved Use

Chronic Hepatitis C

Launch Date

1948
Preventing
Basic research
MASO65D (Xclair®)

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Palliative
Not Provided
511
Unknown

Approved Use

Unknown
Palliative
Phase I
438
Unknown

Approved Use

Unknown
Palliative
Not Provided
511
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Subjects with essential hypertension are more sensitive to the inhibition of 11 beta-HSD by liquorice.
2003-02
Biological activities of synthetic saponins and cardiac glycosides.
2003-01
Photoliberating inositol-1,4,5-trisphosphate triggers ATP release that is blocked by the connexin mimetic peptide gap 26.
2003-01
Blockade of brain stem gap junctions increases phrenic burst frequency and reduces phrenic burst synchronization in adult rat.
2003-01
Smooth muscle membrane potential modulates endothelium-dependent relaxation of rat basilar artery via myo-endothelial gap junctions.
2002-12-15
Short-term cortisol infusion in the brachial artery, with and without inhibiting 11 beta-hydroxysteroid dehydrogenase, does not alter forearm vascular resistance in normotensive and hypertensive subjects.
2002-12
Expression of 11beta-hydroxysteroid dehydrogenase type 1 in adipose tissue is not increased in human obesity.
2002-12
Inhibitors of gap junctions attenuate myogenic tone in cerebral arteries.
2002-12
Acute intrarenal administration of cortisol has no effect on renal blood flow in hypertensive individuals.
2002-11
Bone morphogenetic protein-2 modulation of chondrogenic differentiation in vitro involves gap junction-mediated intercellular communication.
2002-11
Foetal lung maturation in 11beta-hydroxysteroid dehydrogenase type 1 knockout mice.
2002-10
11beta-hydroxysteroid dehydrogenase type 1: a new regulator of fetal lung maturation.
2002-10
Modulation of renal calcium handling by 11 beta-hydroxysteroid dehydrogenase type 2.
2002-10
[Rhabdomyolysis due to licorice ingestion].
2002-09
Inhibition of 3 alpha/beta,20 beta-hydroxysteroid dehydrogenase by dexamethasone, glycyrrhetinic acid and spironolactone is attenuated by deletion of 12 carboxyl-terminal residues.
2002-09
Hepatoprotective effects of 18beta-glycyrrhetinic acid on carbon tetrachloride-induced liver injury: inhibition of cytochrome P450 2E1 expression.
2002-09
Cell coupling and Cx43 expression in embryonic mouse neural progenitor cells.
2002-08-15
[Rhabdomyolysis and arterial hypertension caused by apparent excess of mineralocorticoids: a case report].
2002-08-02
UDP-glucuronic acid:soyasapogenol glucuronosyltransferase involved in saponin biosynthesis in germinating soybean seeds.
2002-08
The role of gap junctions in mediating endothelium-dependent responses to bradykinin in myometrial small arteries isolated from pregnant women.
2002-08
Coordination of mesangial cell contraction by gap junction--mediated intercellular Ca(2+) wave.
2002-08
A puzzling cause of hypokalaemia.
2002-07-20
Critical role of gap junctions in endothelium-dependent hyperpolarization in rat mesenteric arteries.
2002-07
Annexin 1 (lipocortin 1) mimics inhibitory effects of glucocorticoids on testosterone secretion and enhances effects of interleukin-1beta.
2002-06
IL-1beta-induced production of metalloproteinases by synovial cells depends on gap junction conductance.
2002-06
Metabolism of constituents in Huangqin-Tang, a prescription in traditional Chinese medicine, by human intestinal flora.
2002-05
Endothelin 1 type a receptor antagonism prevents vascular dysfunction and hypertension induced by 11beta-hydroxysteroid dehydrogenase inhibition: role of nitric oxide.
2002-04-30
Molecular pharmacophore determination of lipid lowering drugs with the receptor mapping method.
2002-04
Glycyrrhizic acid suppresses type 2 11 beta-hydroxysteroid dehydrogenase expression in vivo.
2002-04
Retinoids inhibit squamous cell carcinoma growth and intercellular communication.
2002-04
Kinetics and mechanism of intercellular ice propagation in a micropatterned tissue construct.
2002-04
Primary afferent fibers establish dye-coupled connections in the frog central nervous system.
2002-03-30
Gap junction intercellular communication propagates cell death in cancerous cells.
2002-03-27
[Licorice--not just candy].
2002-03-20
[Effects of glycyrrhetic acid on transmitter secretion].
2002-03
Induction of inducible nitric oxide synthase expression by 18beta-glycyrrhetinic acid in macrophages.
2002-02-27
11 Beta-hydroxysteroid dehydrogenase type 1 from human liver: dimerization and enzyme cooperativity support its postulated role as glucocorticoid reductase.
2002-02-19
[Effects of glycyrrhetinic acid and IFN-alpha on HSCs collagen metabolism in rat fibrotic liver of varying stages].
2002-02
Blocked gap junctional coupling increases glutamate-induced neurotoxicity in neuron-astrocyte co-cultures.
2002-02
Effect of glycyrrhetinic acid on 11 beta-hydroxysteroid dehydrogenase activity in normotensive and hypertensive subjects.
2002-02
Hydrogen peroxide is an endothelium-derived hyperpolarizing factor in human mesenteric arteries.
2002-01-25
[Quantitative determinations of glycyrrhizic acid, glycyrrhetinic acid, morphine and sodium benzoate in compound liquorice tablets by capillary zone electrophoresis].
2002-01
Influence of honey on the gastrointestinal metabolism and disposition of glycyrrhizin and glycyrrhetic acid in rabbits.
2002-01
Stimulation of the BK(Ca) channel in cultured smooth muscle cells of human trachea by magnolol.
2002-01
An unexpected case of primary pulmonary hypertension of the neonate (PPHN). Potential role of topical administration of enoxolone.
2002
The isolated rat spinal cord as an in vitro model to study the pharmacologic control of myoclonic-like activity.
2002
Enzyme-linked immunosorbent assay for glycyrrhizin using anti-glycyrrhizin monoclonal antibody and an eastern blotting technique for glucuronides of glycyrrhetic acid.
2001-12-15
Effects of glycyrrhetinic acid on collagen metabolism of hepatic stellate cells at different stages of liver fibrosis in rats.
2001-02
[Simultaneous measurements of electrical coupling and action potential transfer in pairs of ventricular cardiomyocytes].
2001
[The assessment of safety of enoxaparin administration during percutaneous transluminal coronary angioplasty after ticlopidine pretreatment. Application of low molecular weigh heparins in prevention of coronary micro-embolization].
2001
Patents

Patents

CN105237609A
16
EP0409005A2
16
EP0472858A2
16
EP2628487A1
16
JP06298668
16
JP2000063254A
16
JP2000143518A
26
JP2000247885A
20
JP2000290199A
28
JP2000512663A
47
JP2001039853A
16
JP2003335651A
17
JP2005220084A
17
JP2007022923A
16
JP2008115109A
16
JP2008222682A
16
JPH0296533A
16
JPH03123465A
16
JPH0315397A
16
JPH03161423A
16
JPH0399023A
26
JPH04207200A
16
JPH0436215A
16
JPH06199648A
16
JPH06279265A
16
JPH07118140A
16
JPH07291857A
16
JPH0748595A
16
JPH09110675A
20
JPH10316555A
16
JPH11139951A
16
JPH11199426A
16
JPS06183145A
16
JPS06251604A
16
JPS06335515A
16
JPS59227812A
20
JPS60260540A
16
JPS61155315A
16
JPS63135351A
16
US20080161377
16
US20110015143
16
US20130143830
16
US20150147357
16
US3164581
16
US5186945
16
US5372744
16
WO2009115455A1
16

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Disodium Glycyrrhizate was not carcinogenic in mice in a drinking water study at exposure levels up to 12.2 mg/kg day(-1) for 96 weeks.
Unknown
Route of Administration: Topical
In Vitro Use Guide
Curator's Comment: The suppressor cell activity of T6S cells was clearly counteracted by glycyrrhizin mononuclear cells (GR-MNC) in vitro in a mixed lymphocyte-tumor cell reaction. The type of cells responsible for anti-suppressor cells in GR-MNC was shown to be a CD4+ CD28+ TCR alpha/beta + Vicia villosa lectin-adherent T cell. These results suggest that GR may reverse the increased susceptibility of thermally injured mice to herpes simplex virus type 1 (HSV) infection through the induction of CD4+ contrasuppressor T cells.
Glycyrrhetinic acid (ENOXOLONE) could inhibit CYP3A4 activity competitively, with a Ki value of 1.57 μM in human liver microsomes.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:15:53 GMT 2025
Edited
by admin
on Mon Mar 31 18:15:53 GMT 2025
Record UNII
6FO62043WK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GLYCYRRHIZIN
HSDB   II   JAN  
Common Name English
GLYCYRRHIZIC ACID
INCI   MART.   MI   USP-RS   WHO-DD  
INCI  
Preferred Name English
Glycyrrhizic acid [WHO-DD]
Common Name English
GLYCYRRHIZIC ACID (GLYCYRRHIZIN) (CONSTITUENT OF LICORICE) [DSC]
Common Name English
GLYCYRRHIZIC ACID [USP-RS]
Common Name English
GLYCYRRHIZIN [JAN]
Common Name English
GLYCYRRHIZIC ACID [MART.]
Common Name English
GLYCYRRHIZIC ACID [MI]
Common Name English
GLYCYRRHIZIN [II]
Common Name English
GLYCYRRHIZINIC ACID
Common Name English
GLYCYRRHIZATE
Common Name English
POTENLINI
Common Name English
GLYCYRRHIZINATE
Common Name English
NSC-167409
Code English
18.BETA.-GLYCYRRHIZIC ACID
Common Name English
.BETA.-GLYCYRRHIZIN
Common Name English
(3.BETA.,20.BETA.)-20-CARBOXY-11-OXO-30-NOROLEAN-12-EN-3-YL 2-O-.BETA.-D-GLUCOPYRANURONOSYL-.ALPHA.-D-GLUCOPYRANOSIDURONIC ACID
Common Name English
NSC-234419
Code English
GLYCYRRHIZIN [HSDB]
Common Name English
GLYCYRON
Common Name English
Classification Tree Code System Code
DSLD 3011 (Number of products:14)
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
WHO-ATC A05BA08
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
WHO-VATC QA05BA08
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
Code System Code Type Description
SMS_ID
100000078200
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
RXCUI
26143
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY RxNorm
EU FOOD ADDITIVES
GLYCYRRHIZIN
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
RXCUI
1370586
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
ALTERNATIVE
EVMPD
SUB14004MIG
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
DAILYMED
6FO62043WK
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
ECHA (EC/EINECS)
215-785-7
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
FDA UNII
6FO62043WK
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
EPA CompTox
DTXSID8047006
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
NSC
167409
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
RXCUI
1359426
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
ALTERNATIVE
CHEBI
29807
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
WIKIPEDIA
GLYCYRRHIZIN
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
HSDB
496
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
DRUG CENTRAL
1325
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
RS_ITEM_NUM
1295888
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
CAS
1405-86-3
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
DRUG BANK
DB13751
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
ChEMBL
CHEMBL441687
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
NSC
234419
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
MERCK INDEX
m5811
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C1117
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
PUBCHEM
14982
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
MESH
D019695
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
CHEBI
15939
Created by admin on Mon Mar 31 18:15:53 GMT 2025 , Edited by admin on Mon Mar 31 18:15:53 GMT 2025
PRIMARY
Related Record Type Details
GLYCYRRHIZA URALENSIS ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
GLYCYRRHIZA INFLATA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
2.49% of dry weight of contents.
Structure of MAGNESIUM GLYCYRRHIZINATE
SALT/SOLVATE -> PARENT
Structure of TRISODIUM GLYCYRRHIZATE
SALT/SOLVATE -> PARENT
LICORICE
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
Structure of AMMONIUM GLYCYRRHIZATE
SALT/SOLVATE -> PARENT
Structure of MONOSODIUM GLYCYRRHIZINATE
SALT/SOLVATE -> PARENT
Structure of ISOGLYCYRRHIZINIC ACID
DERIVATIVE -> PARENT
Structure of TRIPOTASSIUM GLYCYRRHIZINATE
SALT/SOLVATE -> PARENT
Structure of AMMONIUM GLYCYRRHIZINATE TRIHYDRATE
SALT/SOLVATE -> PARENT
GLYCYRRHIZA URALENSIS ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
3.27% of dry weight of contents.
Structure of GLYCYRRHIZINATE DIPOTASSIUM
SALT/SOLVATE -> PARENT
LICORICE ROOT EXTRACT
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of AMMONIUM GLYCYRRHIZATE PENTAHYDRATE
SALT/SOLVATE -> PARENT
GLYCYRRHIZA GLABRA (LICORICE) ROOT POWDER
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (HPLC)
GLYCYRRHIZA URALENSIS ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
The compound did not show significant cytotoxicity against uninfected MDCK cells at 100 uM, but showed inhibitory activity against the H1N1 virus at 100 uM. The compound was also evaluated for anti-HIV activity.
GLYCYRRHIZA URALENSIS (LICORICE) ROOT EXTRACT
PARENT -> CONSTITUENT ALWAYS PRESENT
GLYCYRRHIZA LEPIDOTA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of ENOXOLONE
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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