Page last updated: 2024-12-07

3-oxoglycyrrhetinic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

3-oxoglycyrrhetinic acid, also known as glycyrrhizic acid, is a triterpenoid compound found in licorice root. It has been studied for its various pharmacological effects, including anti-inflammatory, antiviral, and anti-cancer properties. The compound is known to inhibit the production of pro-inflammatory cytokines and modulate the immune response. It has also shown promise in treating viral infections, such as hepatitis C and HIV. Research on 3-oxoglycyrrhetinic acid is ongoing to explore its potential therapeutic applications and elucidate its mechanisms of action. It is a complex molecule with a unique structure that allows it to interact with various biological targets, making it a promising candidate for drug development.'

Cross-References

ID SourceID
PubMed CID111253
CHEMBL ID493512
CHEBI ID16404
SCHEMBL ID18348593

Synonyms (21)

Synonym
CHEBI:16404 ,
3-oxoglycyrrhetinic acid
3,11-dioxoolean-12-en-30-oic acid
C02943
3-oxo-18beta-glycyrrhetinic acid
CHEMBL493512 ,
LMPR0106150012
(2s,4as,6ar,6as,6br,8ar,12as,14br)-2,4a,6a,6b,9,9,12a-heptamethyl-10,13-dioxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-2-carboxylic acid
bdbm50329190
(2s,4as,6as,6br,8ar,12as,12br,14br)-2,4a,6a,6b,9,9,12a-heptamethyl-10,13-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid
3,11-dioxoolean-12-ene-30-oic acid
(18beta,20beta)-3,11-dioxo-olean-12-en-29-oic acid
AKOS016036179
7020-50-0
einecs 230-299-5
(20beta)-3,11-dioxoolean-12-en-29-oic acid
DTXSID70220470
SCHEMBL18348593
Q27101888
(+)-3-oxoglycyrrhetinic acid
(+)-10,13-dioxo-2alpha,4abeta,6aalpha,6bbeta,9,9,-12abeta-heptamethyl -1,2,3,4,4a,5,6,6a,6b,7,8,8aalpha,9,10,11,12,12a,12balpha,13,14bbeta -icosahydropicene-2beta-carboxylic acid

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"Human carboxylesterase 2 (hCE2), one of the major carboxylesterases in the human intestine and various tumour tissues, plays important roles in the oral bioavailability and treatment outcomes of ester- or amide-containing drugs or prodrugs, such as anticancer agents CPT-11 (irinotecan) and LY2334737 (gemcitabine)."( Design, synthesis, and structure-activity relationship study of glycyrrhetinic acid derivatives as potent and selective inhibitors against human carboxylesterase 2.
Ge, GB; Hao, DC; Hou, J; Jin, Q; Li, YG; Wang, P; Yang, L; Zhou, K; Zou, LW, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pentacyclic triterpenoid
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Corticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)IC50 (µMol)0.61900.00411.066710.0000AID526983
Corticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)IC50 (µMol)0.32900.00040.63676.4300AID526982
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
lung developmentCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
steroid catabolic processCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
response to hypoxiaCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
regulation of blood volume by renal aldosteroneCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
female pregnancyCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
response to xenobiotic stimulusCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
response to foodCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
response to insulinCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
cortisol metabolic processCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
response to glucocorticoidCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
glucocorticoid metabolic processCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein homodimerization activityCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
7-beta-hydroxysteroid dehydrogenase (NADP+) activityCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
NADP bindingCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
11-beta-hydroxysteroid dehydrogenase (NADP+) activityCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
cortisol dehydrogenase activityCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
steroid bindingCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
steroid bindingCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
NAD bindingCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
11-beta-hydroxysteroid dehydrogenase (NAD+) activityCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
membraneCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
endoplasmic reticulum membraneCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
intracellular membrane-bounded organelleCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
endoplasmic reticulum membraneCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
intracellular membrane-bounded organelleCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
intracellular membrane-bounded organelleCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (40)

Assay IDTitleYearJournalArticle
AID690623Cytotoxicity against human HT-29 cells after 96 hrs by SRB assay2011European journal of medicinal chemistry, Nov, Volume: 46, Issue:11
Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives.
AID690617Cytotoxicity against human 518A2 cells after 96 hrs by SRB assay2011European journal of medicinal chemistry, Nov, Volume: 46, Issue:11
Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives.
AID659367Selectivity index, ratio of CC50 for human HepG2(2.2.15) cells to IC50 for HBV by hepatitis B e-antigen release detection assay2012Bioorganic & medicinal chemistry letters, May-15, Volume: 22, Issue:10
Synthesis, biological evaluation and structure-activity relationships of glycyrrhetinic acid derivatives as novel anti-hepatitis B virus agents.
AID418487Inhibition of superoxide anion induced DNA damage of Escherichia coli pBR322 at 300 uM by gel electrophoresis2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
Synthesis, anti-inflammatory, and antioxidant activities of 18beta-glycyrrhetinic acid derivatives as chemical mediators and xanthine oxidase inhibitors.
AID659363Cytotoxicity against human HepG2(2.2.15) cells2012Bioorganic & medicinal chemistry letters, May-15, Volume: 22, Issue:10
Synthesis, biological evaluation and structure-activity relationships of glycyrrhetinic acid derivatives as novel anti-hepatitis B virus agents.
AID659368Antiviral activity against Hepatitis B virus infected in human HepG2(2.2.15) cells assessed as reduction in viral DNA replication2012Bioorganic & medicinal chemistry letters, May-15, Volume: 22, Issue:10
Synthesis, biological evaluation and structure-activity relationships of glycyrrhetinic acid derivatives as novel anti-hepatitis B virus agents.
AID526982Inhibition of human recombinant 11beta-HSD2 expressed in HEK293 cells assessed as conversion of [1,2,6,7-3H]-cortisol to cortisone by scintillation counting2010Bioorganic & medicinal chemistry, Nov-01, Volume: 18, Issue:21
Synthesis of novel 3-amino and 29-hydroxamic acid derivatives of glycyrrhetinic acid as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors.
AID1285099Inhibition of CE2 in human liver microsomes using fluorescein diacetate as substrate preincubated for 10 mins followed by substrate addition measured after 30 mins by LC-UV analysis2016European journal of medicinal chemistry, Apr-13, Volume: 112Design, synthesis, and structure-activity relationship study of glycyrrhetinic acid derivatives as potent and selective inhibitors against human carboxylesterase 2.
AID418480Inhibition of fMLP/cytochalasin B-stimulated super oxide anion generation in Sprague-Dawley rat neutrophils2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
Synthesis, anti-inflammatory, and antioxidant activities of 18beta-glycyrrhetinic acid derivatives as chemical mediators and xanthine oxidase inhibitors.
AID526979Inhibition of human recombinant 11beta-HSD1 expressed in HEK293 cells assessed as residual conversion of [1,2-3H]-cortisone to cortisol at 1 uM by scintillation counting2010Bioorganic & medicinal chemistry, Nov-01, Volume: 18, Issue:21
Synthesis of novel 3-amino and 29-hydroxamic acid derivatives of glycyrrhetinic acid as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors.
AID587114Inhibition of human 11beta-HSD2 expressed in HEK293 cells assessed as residual conversion of [1,2,6,7-[3H]cortisol to cortisone at 1000 nM after 10 mins by scintillation counting2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Synthesis of new glycyrrhetinic acid derived ring A azepanone, 29-urea and 29-hydroxamic acid derivatives as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors.
AID690621Cytotoxicity against human A431 cells after 96 hrs by SRB assay2011European journal of medicinal chemistry, Nov, Volume: 46, Issue:11
Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives.
AID526978Inhibition of human recombinant 11beta-HSD2 expressed in HEK293 cells assessed as residual conversion of [1,2,6,7-3H]-cortisol to cortisone at 1 uM by scintillation counting2010Bioorganic & medicinal chemistry, Nov-01, Volume: 18, Issue:21
Synthesis of novel 3-amino and 29-hydroxamic acid derivatives of glycyrrhetinic acid as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors.
AID526983Inhibition of human recombinant 11beta-HSD1 expressed in HEK293 cells assessed as conversion of [1,2-3H]-cortisone to cortisol by scintillation counting2010Bioorganic & medicinal chemistry, Nov-01, Volume: 18, Issue:21
Synthesis of novel 3-amino and 29-hydroxamic acid derivatives of glycyrrhetinic acid as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors.
AID659366Antiviral activity against Hepatitis B virus infected in human HepG2(2.2.15) cells assessed as reduction in hepatitis B e-antigen release2012Bioorganic & medicinal chemistry letters, May-15, Volume: 22, Issue:10
Synthesis, biological evaluation and structure-activity relationships of glycyrrhetinic acid derivatives as novel anti-hepatitis B virus agents.
AID456097Inhibition 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 counting2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Synthesis of glycyrrhetinic acid derivatives for the treatment of metabolic diseases.
AID690620Cytotoxicity against human A549 cells after 96 hrs by SRB assay2011European journal of medicinal chemistry, Nov, Volume: 46, Issue:11
Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives.
AID526984Selectivity ratio of IC50 for human recombinant 11beta-HSD2 to IC50 for human recombinant 11beta-HSD12010Bioorganic & medicinal chemistry, Nov-01, Volume: 18, Issue:21
Synthesis of novel 3-amino and 29-hydroxamic acid derivatives of glycyrrhetinic acid as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors.
AID690624Cytotoxicity against human Lipo cells after 96 hrs by SRB assay2011European journal of medicinal chemistry, Nov, Volume: 46, Issue:11
Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives.
AID418483Inhibition of LPS-induced nitric oxide generation in mouse RAW264.7 cells at 30 uM pretreated 1 hr before LPS challenge by Griess method2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
Synthesis, anti-inflammatory, and antioxidant activities of 18beta-glycyrrhetinic acid derivatives as chemical mediators and xanthine oxidase inhibitors.
AID380021Toxicity against rat neonatal brain microglia cells assessed as phorbol-12-myristate-13-acetate-stimulated LDH release2000Journal of natural products, May, Volume: 63, Issue:5
Bioactive 12-oleanene triterpene and secotriterpene acids from Maytenus undata.
AID418489Inhibition of xanthine oxidase2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
Synthesis, anti-inflammatory, and antioxidant activities of 18beta-glycyrrhetinic acid derivatives as chemical mediators and xanthine oxidase inhibitors.
AID608127Cytotoxicity against human NTUB1 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry, Jul-15, Volume: 19, Issue:14
18β-Glycyrrhetinic acid derivatives induced mitochondrial-mediated apoptosis through reactive oxygen species-mediated p53 activation in NTUB1 cells.
AID690619Cytotoxicity against human DLD1 cells after 96 hrs by SRB assay2011European journal of medicinal chemistry, Nov, Volume: 46, Issue:11
Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives.
AID418482Inhibition of LPS-induced nitric oxide generation in mouse RAW264.7 cells pretreated 1 hr before LPS challenge by Griess method2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
Synthesis, anti-inflammatory, and antioxidant activities of 18beta-glycyrrhetinic acid derivatives as chemical mediators and xanthine oxidase inhibitors.
AID659365Selectivity index, ratio of CC50 for human HepG2(2.2.15) cells to IC50 for HBV by hepatitis B surface antigen release detection assay2012Bioorganic & medicinal chemistry letters, May-15, Volume: 22, Issue:10
Synthesis, biological evaluation and structure-activity relationships of glycyrrhetinic acid derivatives as novel anti-hepatitis B virus agents.
AID456095Inhibition 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 counting2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Synthesis of glycyrrhetinic acid derivatives for the treatment of metabolic diseases.
AID418488Antioxidant activity assessed as DPPH radical scavenging activity2009Bioorganic & medicinal chemistry, Apr-01, Volume: 17, Issue:7
Synthesis, anti-inflammatory, and antioxidant activities of 18beta-glycyrrhetinic acid derivatives as chemical mediators and xanthine oxidase inhibitors.
AID690625Cytotoxicity against human MCF7 cells after 96 hrs by SRB assay2011European journal of medicinal chemistry, Nov, Volume: 46, Issue:11
Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives.
AID690616Cytotoxicity against human HCT8 cells after 96 hrs by SRB assay2011European journal of medicinal chemistry, Nov, Volume: 46, Issue:11
Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives.
AID380020Antiinflammatory activity in rat neonatal brain microglia cells assessed as effect on phorbol-12-myristate-13-acetate-stimulated thromboxane B2 release2000Journal of natural products, May, Volume: 63, Issue:5
Bioactive 12-oleanene triterpene and secotriterpene acids from Maytenus undata.
AID690626Cytotoxicity against human SW1736 cells after 96 hrs by SRB assay2011European journal of medicinal chemistry, Nov, Volume: 46, Issue:11
Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives.
AID587111Inhibition of human recombinant 11beta-HSD1 expressed in HEK293 cells assessed as residual conversion of [1,2-[3H]cortisone to cortisol at 1000 nM after 10 mins by scintillation counting2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Synthesis of new glycyrrhetinic acid derived ring A azepanone, 29-urea and 29-hydroxamic acid derivatives as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors.
AID1285100Inhibition of CE1 in human liver microsomes using 2-(2-Benzoyl-3-methoxyphenyl) benzothiazole as substrate preincubated for 10 mins followed by substrate addition measured after 30 mins by LC-UV analysis2016European journal of medicinal chemistry, Apr-13, Volume: 112Design, synthesis, and structure-activity relationship study of glycyrrhetinic acid derivatives as potent and selective inhibitors against human carboxylesterase 2.
AID690622Cytotoxicity against human A253 cells after 96 hrs by SRB assay2011European journal of medicinal chemistry, Nov, Volume: 46, Issue:11
Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives.
AID659364Antiviral activity against Hepatitis B virus infected in human HepG2(2.2.15) cells assessed as reduction in hepatitis B surface antigen release2012Bioorganic & medicinal chemistry letters, May-15, Volume: 22, Issue:10
Synthesis, biological evaluation and structure-activity relationships of glycyrrhetinic acid derivatives as novel anti-hepatitis B virus agents.
AID690618Cytotoxicity against human HCT116 cells after 96 hrs by SRB assay2011European journal of medicinal chemistry, Nov, Volume: 46, Issue:11
Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives.
AID1917383Cytotoxicity against human HDF cells assessed as reduction in cell viability at 10 uM incubated for 24 hrs by MTT assay2022Bioorganic & medicinal chemistry letters, 11-15, Volume: 76Photoprotective effect of 18β-glycyrrhetinic acid derivatives against ultra violet (UV)-B-Induced skin aging.
AID380019Antiinflammatory activity in rat neonatal brain microglia cells assessed as effect on phorbol-12-myristate-13-acetate-stimulated superoxide release2000Journal of natural products, May, Volume: 63, Issue:5
Bioactive 12-oleanene triterpene and secotriterpene acids from Maytenus undata.
AID659369Selectivity index, ratio of CC50 for human HepG2(2.2.15) cells to IC50 for HBV by viral DNA replication detection assay2012Bioorganic & medicinal chemistry letters, May-15, Volume: 22, Issue:10
Synthesis, biological evaluation and structure-activity relationships of glycyrrhetinic acid derivatives as novel anti-hepatitis B virus agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (20.00)29.6817
2010's7 (70.00)24.3611
2020's1 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.57

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.57 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.96 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.57)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]