Page last updated: 2024-11-12

riccardin c

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Description

riccardin C: isolated from liverworts; functions as a liver X receptor (LXR)alpha agonist and an LXRbeta antagonist; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10070992
CHEMBL ID411317
SCHEMBL ID22704770
MeSH IDM0492124

Synonyms (14)

Synonym
riccardin c
14-oxapentacyclo[20.2.2.2^{10,13}.1^{15,19}.0^{2,7}]nonacosa-1(25),2(7),3,5,10,12,15,17,19(27),22(26),23,28-dodecaene-5,16,24-triol
bdbm23839
CHEMBL411317
riccardi c
Q7322888
SCHEMBL22704770
1,2,13,14-tetrahydro-3,6:15,18-dietheno-8,12-metheno-12h-7-benzoxacycloeicosin-9,17,21-triol
3,6:15,18-dietheno-8,12-metheno-12h-7-benzoxacycloeicosin-9,17,21-triol, 1,2,13,14-tetrahydro-
r9th5vm6bd ,
84575-08-6
DTXSID101030291
14-oxapentacyclo[20.2.2.210,13.115,19.02,7]nonacosa-1(24),2(7),3,5,10(29),11,13(28),15,17,19(27),22,25-dodecaene-5,16,24-triol
14-oxapentacyclo[20.2.2.2{10,13}.1{15,19}.0{2,7}]nonacosa-1(24),2,4,6,10,12,15(27),16,18,22,25,28-dodecaene-5,16,24-triol
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Alpha-glucosidase MAL32Saccharomyces cerevisiae S288CIC50 (µMol)8.25004.80007.10009.9000AID1798364
Oxysterols receptor LXR-betaHomo sapiens (human)IC50 (µMol)7.70000.00790.92859.9000AID1798364; AID328048
Oxysterols receptor LXR-alphaHomo sapiens (human)IC50 (µMol)6.57500.00901.06049.9000AID1798364; AID1798365; AID328047
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (43)

Processvia Protein(s)Taxonomy
hormone-mediated signaling pathwayOxysterols receptor LXR-betaHomo sapiens (human)
negative regulation of macrophage derived foam cell differentiationOxysterols receptor LXR-betaHomo sapiens (human)
positive regulation of triglyceride biosynthetic processOxysterols receptor LXR-betaHomo sapiens (human)
positive regulation of cholesterol effluxOxysterols receptor LXR-betaHomo sapiens (human)
positive regulation of lipid storageOxysterols receptor LXR-betaHomo sapiens (human)
negative regulation of cholesterol storageOxysterols receptor LXR-betaHomo sapiens (human)
intracellular receptor signaling pathwayOxysterols receptor LXR-betaHomo sapiens (human)
negative regulation of lipid transportOxysterols receptor LXR-betaHomo sapiens (human)
positive regulation of cholesterol transportOxysterols receptor LXR-betaHomo sapiens (human)
phosphatidylcholine acyl-chain remodelingOxysterols receptor LXR-betaHomo sapiens (human)
cholesterol homeostasisOxysterols receptor LXR-betaHomo sapiens (human)
mRNA transcription by RNA polymerase IIOxysterols receptor LXR-betaHomo sapiens (human)
positive regulation of fatty acid biosynthetic processOxysterols receptor LXR-betaHomo sapiens (human)
negative regulation of proteolysisOxysterols receptor LXR-betaHomo sapiens (human)
negative regulation of DNA-templated transcriptionOxysterols receptor LXR-betaHomo sapiens (human)
positive regulation of DNA-templated transcriptionOxysterols receptor LXR-betaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIOxysterols receptor LXR-betaHomo sapiens (human)
negative regulation of pinocytosisOxysterols receptor LXR-betaHomo sapiens (human)
positive regulation of lipoprotein lipase activityOxysterols receptor LXR-betaHomo sapiens (human)
positive regulation of protein metabolic processOxysterols receptor LXR-betaHomo sapiens (human)
negative regulation of type II interferon-mediated signaling pathwayOxysterols receptor LXR-betaHomo sapiens (human)
positive regulation of high-density lipoprotein particle assemblyOxysterols receptor LXR-betaHomo sapiens (human)
positive regulation of pancreatic juice secretionOxysterols receptor LXR-betaHomo sapiens (human)
positive regulation of secretion of lysosomal enzymesOxysterols receptor LXR-betaHomo sapiens (human)
negative regulation of cold-induced thermogenesisOxysterols receptor LXR-betaHomo sapiens (human)
positive regulation of miRNA transcriptionOxysterols receptor LXR-betaHomo sapiens (human)
negative regulation of response to endoplasmic reticulum stressOxysterols receptor LXR-betaHomo sapiens (human)
cell differentiationOxysterols receptor LXR-betaHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIOxysterols receptor LXR-betaHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIOxysterols receptor LXR-alphaHomo sapiens (human)
hormone-mediated signaling pathwayOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of macrophage derived foam cell differentiationOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of triglyceride biosynthetic processOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of cholesterol effluxOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of cholesterol storageOxysterols receptor LXR-alphaHomo sapiens (human)
intracellular receptor signaling pathwayOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of lipid transportOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of cholesterol transportOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of transporter activityOxysterols receptor LXR-alphaHomo sapiens (human)
response to progesteroneOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of toll-like receptor 4 signaling pathwayOxysterols receptor LXR-alphaHomo sapiens (human)
phosphatidylcholine acyl-chain remodelingOxysterols receptor LXR-alphaHomo sapiens (human)
cholesterol homeostasisOxysterols receptor LXR-alphaHomo sapiens (human)
regulation of circadian rhythmOxysterols receptor LXR-alphaHomo sapiens (human)
mRNA transcription by RNA polymerase IIOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of macrophage activationOxysterols receptor LXR-alphaHomo sapiens (human)
apoptotic cell clearanceOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of fatty acid biosynthetic processOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of proteolysisOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of DNA-templated transcriptionOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of lipid biosynthetic processOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of pinocytosisOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of inflammatory responseOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of lipoprotein lipase activityOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of protein metabolic processOxysterols receptor LXR-alphaHomo sapiens (human)
lipid homeostasisOxysterols receptor LXR-alphaHomo sapiens (human)
sterol homeostasisOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of type II interferon-mediated signaling pathwayOxysterols receptor LXR-alphaHomo sapiens (human)
triglyceride homeostasisOxysterols receptor LXR-alphaHomo sapiens (human)
cellular response to lipopolysaccharideOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of pancreatic juice secretionOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of secretion of lysosomal enzymesOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of cold-induced thermogenesisOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of response to endoplasmic reticulum stressOxysterols receptor LXR-alphaHomo sapiens (human)
cell differentiationOxysterols receptor LXR-alphaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingOxysterols receptor LXR-betaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificOxysterols receptor LXR-betaHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificOxysterols receptor LXR-betaHomo sapiens (human)
DNA bindingOxysterols receptor LXR-betaHomo sapiens (human)
protein bindingOxysterols receptor LXR-betaHomo sapiens (human)
zinc ion bindingOxysterols receptor LXR-betaHomo sapiens (human)
chromatin DNA bindingOxysterols receptor LXR-betaHomo sapiens (human)
apolipoprotein A-I receptor bindingOxysterols receptor LXR-betaHomo sapiens (human)
nuclear retinoid X receptor bindingOxysterols receptor LXR-betaHomo sapiens (human)
ATPase bindingOxysterols receptor LXR-betaHomo sapiens (human)
nuclear receptor activityOxysterols receptor LXR-betaHomo sapiens (human)
transcription cis-regulatory region bindingOxysterols receptor LXR-alphaHomo sapiens (human)
transcription cis-regulatory region bindingOxysterols receptor LXR-alphaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificOxysterols receptor LXR-alphaHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificOxysterols receptor LXR-alphaHomo sapiens (human)
DNA bindingOxysterols receptor LXR-alphaHomo sapiens (human)
nuclear receptor activityOxysterols receptor LXR-alphaHomo sapiens (human)
protein bindingOxysterols receptor LXR-alphaHomo sapiens (human)
zinc ion bindingOxysterols receptor LXR-alphaHomo sapiens (human)
cholesterol bindingOxysterols receptor LXR-alphaHomo sapiens (human)
chromatin DNA bindingOxysterols receptor LXR-alphaHomo sapiens (human)
sterol response element bindingOxysterols receptor LXR-alphaHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingOxysterols receptor LXR-alphaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
nucleusOxysterols receptor LXR-betaHomo sapiens (human)
nucleoplasmOxysterols receptor LXR-betaHomo sapiens (human)
cytoplasmOxysterols receptor LXR-betaHomo sapiens (human)
cytosolOxysterols receptor LXR-betaHomo sapiens (human)
RNA polymerase II transcription regulator complexOxysterols receptor LXR-betaHomo sapiens (human)
chromatinOxysterols receptor LXR-betaHomo sapiens (human)
nucleusOxysterols receptor LXR-betaHomo sapiens (human)
nucleusOxysterols receptor LXR-alphaHomo sapiens (human)
nucleoplasmOxysterols receptor LXR-alphaHomo sapiens (human)
cytoplasmOxysterols receptor LXR-alphaHomo sapiens (human)
cytosolOxysterols receptor LXR-alphaHomo sapiens (human)
RNA polymerase II transcription regulator complexOxysterols receptor LXR-alphaHomo sapiens (human)
chromatinOxysterols receptor LXR-alphaHomo sapiens (human)
receptor complexOxysterols receptor LXR-alphaHomo sapiens (human)
nucleusOxysterols receptor LXR-alphaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (27)

Assay IDTitleYearJournalArticle
AID1798365Reporter Gene Assay from Article 10.1016/j.bmc.2008.02.078: \\Co-existence of alpha-glucosidase-inhibitory and liver X receptor-regulatory activities and their separation by structural development.\\2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Co-existence of alpha-glucosidase-inhibitory and liver X receptor-regulatory activities and their separation by structural development.
AID1798364alpha-Glucosidase Inhibition Assay from Article 10.1016/j.bmc.2008.02.078: \\Co-existence of alpha-glucosidase-inhibitory and liver X receptor-regulatory activities and their separation by structural development.\\2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Co-existence of alpha-glucosidase-inhibitory and liver X receptor-regulatory activities and their separation by structural development.
AID328047Antagonist activity at human recombinant LXRalpha expressed in HEK293 cells by luciferase reporter gene assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Co-existence of alpha-glucosidase-inhibitory and liver X receptor-regulatory activities and their separation by structural development.
AID602901Vasorelaxant activity in Wistar rat endothelium-denuded aortic rings assessed as inhibition of phenylephrine-induced contractions at 10 to 100 uM after 10 to 60 mins2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Vasorelaxant effects of macrocyclic bis(bibenzyls) from liverworts.
AID1625243Cytotoxic activity against human A549 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay2019Journal of natural products, 04-26, Volume: 82, Issue:4
Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata.
AID1059059Antibacterial activity against 2-phenoxyphenol and trichlosan-resistant Staphylococcus aureus clinical isolate N315 by liquid microdilution method2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Structure-anti-MRSA activity relationship of macrocyclic bis(bibenzyl) derivatives.
AID602898Vasorelaxant activity in Wistar rat endothelium-intact aortic rings assessed as inhibition of phenylephrine-induced contractions after 10 to 60 mins2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Vasorelaxant effects of macrocyclic bis(bibenzyls) from liverworts.
AID328049Agonist activity at LXR2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Co-existence of alpha-glucosidase-inhibitory and liver X receptor-regulatory activities and their separation by structural development.
AID328046Inhibition of Saccharomyces sp. alpha-glucosidase2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Co-existence of alpha-glucosidase-inhibitory and liver X receptor-regulatory activities and their separation by structural development.
AID1625245Cytotoxic activity against human MRC5 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay2019Journal of natural products, 04-26, Volume: 82, Issue:4
Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata.
AID1059061Antibacterial activity against methicillin-resistant Staphylococcus aureus clinical isolate OM584 by liquid microdilution method2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Structure-anti-MRSA activity relationship of macrocyclic bis(bibenzyl) derivatives.
AID1059060Antibacterial activity against methicillin-resistant Staphylococcus aureus clinical isolate N315 by liquid microdilution method2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Structure-anti-MRSA activity relationship of macrocyclic bis(bibenzyl) derivatives.
AID1059058Antibacterial activity against methicillin-resistant Staphylococcus aureus at 4 times MIC by cell survival assay2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Structure-anti-MRSA activity relationship of macrocyclic bis(bibenzyl) derivatives.
AID1296789Antimicrobial activity against methicillin-resistant Staphylococcus aureus OM481 clinical isolate after 18 to 20 hrs by liquid microdilution method2016Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9
Minimum structural requirements for cell membrane leakage-mediated anti-MRSA activity of macrocyclic bis(bibenzyl)s.
AID602900Vasorelaxant activity in Wistar rat endothelium-intact aortic rings assessed as inhibition of phenylephrine-induced contractions at 10 to 100 uM after 10 to 60 mins2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Vasorelaxant effects of macrocyclic bis(bibenzyls) from liverworts.
AID371665Activation of full length LXRbeta expressed in african green monkey COS7 cells co-transfected with RXRalpha assessed as increase in LXR-response element driven luciferase reporter gene transactivation after 24 hrs2009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Synthesis of riccardin C and its seven analogues. Part 1: The role of their phenolic hydroxy groups as LXRalpha agonists.
AID371664Agonist activity at full length LXRalpha expressed in african green monkey COS7 cells co-transfected with RXRalpha assessed as increase in LXR-response element driven luciferase reporter gene transactivation after 24 hrs2009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Synthesis of riccardin C and its seven analogues. Part 1: The role of their phenolic hydroxy groups as LXRalpha agonists.
AID717874Antibacterial activity against methicillin-resistant Staphylococcus aureus OM481 by two-fold liquid microdilution method2012Bioorganic & medicinal chemistry letters, Dec-15, Volume: 22, Issue:24
Riccardin C derivatives as anti-MRSA agents: structure-activity relationship of a series of hydroxylated bis(bibenzyl)s.
AID404052Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells pretreated 1 hr before LPS challenge after 24 hrs by Griess reagent method2005Journal of natural products, Dec, Volume: 68, Issue:12
Bis(bibenzyls) from liverworts inhibit lipopolysaccharide-induced inducible NOS in RAW 264.7 cells: a study of structure-activity relationships and molecular mechanism.
AID371663Agonist activity at full length LXRalpha expressed in african green monkey COS7 cells co-transfected with RXRalpha assessed as increase in LXR-response element driven luciferase reporter gene transactivation at 30 mmol/L after 24 hrs relative to control2009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Synthesis of riccardin C and its seven analogues. Part 1: The role of their phenolic hydroxy groups as LXRalpha agonists.
AID717875Antibacterial activity against methicillin-resistant Staphylococcus aureus OM584 by two-fold liquid microdilution method2012Bioorganic & medicinal chemistry letters, Dec-15, Volume: 22, Issue:24
Riccardin C derivatives as anti-MRSA agents: structure-activity relationship of a series of hydroxylated bis(bibenzyl)s.
AID1059062Antibacterial activity against methicillin-resistant Staphylococcus aureus clinical isolate OM481 by liquid microdilution method2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Structure-anti-MRSA activity relationship of macrocyclic bis(bibenzyl) derivatives.
AID1296790Antimicrobial activity against 2-phenoxyphenol/methicillin-resistant Staphylococcus aureus after 18 to 20 hrs by liquid microdilution method2016Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9
Minimum structural requirements for cell membrane leakage-mediated anti-MRSA activity of macrocyclic bis(bibenzyl)s.
AID1296788Antimicrobial activity against methicillin-resistant Staphylococcus aureus N315 after 18 to 20 hrs by liquid microdilution method2016Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9
Minimum structural requirements for cell membrane leakage-mediated anti-MRSA activity of macrocyclic bis(bibenzyl)s.
AID328048Antagonist activity at human recombinant LXRbeta expressed in HEK293 cells by luciferase reporter gene assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Co-existence of alpha-glucosidase-inhibitory and liver X receptor-regulatory activities and their separation by structural development.
AID602897Vasorelaxant activity in Wistar rat endothelium-intact aortic rings assessed as inhibition of phenylephrine-induced contractions at 30 uM after 10 to 30 mins2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Vasorelaxant effects of macrocyclic bis(bibenzyls) from liverworts.
AID602899Vasorelaxant activity in Wistar rat endothelium-intact aortic rings assessed as inhibition of phenylephrine-induced contractions at 10 to 100 uM2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Vasorelaxant effects of macrocyclic bis(bibenzyls) from liverworts.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (19)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (26.32)29.6817
2010's13 (68.42)24.3611
2020's1 (5.26)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.76

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 Index11.76 (24.57)
Research Supply Index3.00 (2.92)
Research Growth Index4.76 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.76)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (15.79%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other16 (84.21%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]