Page last updated: 2024-12-11

oleandrigenin

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

Description

oleandrigenin: RN given refers to (3beta)-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

oleandrigenin : A steroid ester that is the 16-acetyl derivative of gitoxigenin. [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]

Cross-References

ID SourceID
PubMed CID9802865
CHEMBL ID374839
CHEBI ID63508
SCHEMBL ID4905625
MeSH IDM0052772

Synonyms (30)

Synonym
nsc 148790
einecs 207-359-4
card-20(22)-enolide, 16-(acetyloxy)-3,14-dihydroxy-, (3beta,5beta,16beta)-
5-beta-card-20(22)-enolide, 3-beta,14,16-beta-trihydroxy-, 16-acetate
16-acetylgitoxigenin
gitoxigenine 16-acetate
oleandrisenin
gitoxigenin 16-acetate
3beta,14,16beta-trihydroxy-5-betacard-20(22)-enolide 16-acetate
card-20(22)-enolide, 16-(acetyloxy)-3,14-dihydroxy-, (3-beta,5-beta,16-beta)-
oleandrigenin
465-15-6
nsc-148790
CHEMBL374839
chebi:63508 ,
gq25uyw4qv ,
unii-gq25uyw4qv
16beta-acetoxy-3beta,14-dihydroxy-5beta,14beta-card-20(22)-enolide
(3beta,5beta,16beta)-16-acetoxy-3,14-dihydroxycard-20(22)-enolide
16-o-acetylgitoxigenin
SCHEMBL4905625
(3.beta.,5.beta.,16.beta.)-16-(acetyloxy)-3,14-dihydroxycard-20(22)-enolide
card-20(22)-enolide, 16-(acetyloxy)-3,14-dihydroxy-, (3.beta.,5.beta.,16.beta.)-
5.beta.-card-20(22)-enolide, 3.beta.,14,16.beta.-trihydroxy-, 16-acetate
AKOS032437983
(3beta,5beta,16beta)-16-(acetyloxy)-3,14-dihydroxycard-20(22)-enolide
5beta-card-20(22)-enolide, 3beta,14,16beta-trihydroxy-, 16-acetate
3 alpha,14-dihydroxy-16 beta-acetoxy-5 beta,14 beta-card-20(22)-enolide
oleandrigenin (oleandrin)
Q27132662
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitorAn EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of Na(+)/K(+)-transporting ATPase (EC 3.6.3.9).
[role 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]

Drug Classes (3)

ClassDescription
14beta-hydroxy steroidA 14-hydroxy steroid in which the hydroxy group has a beta-configuration.
3beta-hydroxy steroidA 3-hydroxy steroid in which the 3-hydroxy substituent is in the beta-position.
steroid ester
[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]

Bioassays (30)

Assay IDTitleYearJournalArticle
AID292170Growth inhibition of human HepG2 cells2007Journal of natural products, Jul, Volume: 70, Issue:7
Bioactive cardenolides from the stems and twigs of Nerium oleander.
AID1740516Induction of apoptosis in human HeLa cells assessed as reduction in Rb phosphorylation at 1 to 10 uM incubated for 24 hrs by Western blotting analysis
AID1740504Cytotoxicity against human BJ cells assessed as reduction in cell viability incubated for 72 hrs by resazurin assay
AID1570110Antiproliferative activity against human Hep3B cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay
AID1740519Downregulation of p53 protein expression in human HeLa cells at 1 to 10 uM incubated for 24 hrs by Western blotting analysis
AID1740512Induction of apoptosis in human HeLa cells assessed as increase in caspase 7 fragmentation at 1 to 10 uM incubated for 24 hrs by Western blotting analysis
AID292165Inhibition of induction of ICAM1 expression in human A549 cells in presence of TNFalpha after 1 hr2007Journal of natural products, Jul, Volume: 70, Issue:7
Bioactive cardenolides from the stems and twigs of Nerium oleander.
AID292167Viability of human A549 cells by MTT assay after 24 hrs2007Journal of natural products, Jul, Volume: 70, Issue:7
Bioactive cardenolides from the stems and twigs of Nerium oleander.
AID1570107Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay
AID1740506Induction of cell cycle arrest in human HeLa cells assessed as decrease in accumulation of cells at G0/G1 phase at 1 to 10 uM incubated for 24 hrs by PI staining based flow cytometry analysis relative to control
AID1740505Inhibition of porcine kidney Na+/K+ ATPase at 50 uM assessed as enzyme residual activity using ATP as substrate incubated for 2 mins followed by substrate addition and measured after 6 mins (Rvb = 100 +/-3.16%)
AID1740501Cytotoxicity against human CEM cells assessed as reduction in cell viability incubated for 72 hrs by resazurin assay
AID292166Inhibition of induction of ICAM1 expression in human A549 cells in presence of IL1-alpha after 1 hr2007Journal of natural products, Jul, Volume: 70, Issue:7
Bioactive cardenolides from the stems and twigs of Nerium oleander.
AID1570112Inhibition of porcine kidney Na+/K+-ATPase assessed as residual activity at 50 uM preincubated for 2 mins followed by ATP addition and measured after 6 mins by bagin-sky assay relative to untreated control
AID1570106Antiproliferative activity against human CEM cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay
AID1740503Cytotoxicity against human HeLa cells assessed as reduction in cell viability incubated for 72 hrs by resazurin assay
AID1740510Induction of apoptosis in human HeLa cells assessed as fold increase in caspase 3/7 activity at 1 to 10 uM incubated for 24 hrs by fluorescence based assay relative to control
AID292172Reversal of multidrug resistance assessed as effect on calcein accumulation in MDR-human 2780 AD cells at 2.5 ug/ml relative to control2007Journal of natural products, Jul, Volume: 70, Issue:7
Bioactive cardenolides from the stems and twigs of Nerium oleander.
AID1570109Antiproliferative activity against human A2780 cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay
AID1740502Cytotoxicity against human MCF7 cells assessed as reduction in cell viability incubated for 72 hrs by resazurin assay
AID1740518Induction of apoptosis in human HeLa cells assessed as reduction in Rb level at 1 to 10 uM incubated for 24 hrs by Western blotting analysis
AID292173Reversal of multidrug resistance assessed as effect on calcein accumulation in MDR-human 2780 AD cells at 25 ug/ml relative to control2007Journal of natural products, Jul, Volume: 70, Issue:7
Bioactive cardenolides from the stems and twigs of Nerium oleander.
AID1570108Antiproliferative activity against human HeLa cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay
AID292171Reversal of multidrug resistance assessed as effect on calcein accumulation in MDR-human 2780 AD cells at 0.25 ug/ml relative to control2007Journal of natural products, Jul, Volume: 70, Issue:7
Bioactive cardenolides from the stems and twigs of Nerium oleander.
AID127479Binding affinity against murine monoclonal antibody (mAb)-40-502002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
Three-dimensional quantitative structure-activity relationship analysis of ligand binding to human sequence antidigoxin monoclonal antibodies using comparative molecular field analysis.
AID1740511Induction of apoptosis in human HeLa cells assessed as increase in PARP-1 cleavage at 10 uM incubated for 24 hrs by Western blotting analysis
AID292168Growth inhibition of human WI38 cells2007Journal of natural products, Jul, Volume: 70, Issue:7
Bioactive cardenolides from the stems and twigs of Nerium oleander.
AID292169Growth inhibition of human VA13 cells2007Journal of natural products, Jul, Volume: 70, Issue:7
Bioactive cardenolides from the stems and twigs of Nerium oleander.
AID146869In vitro inhibition of hog kidney Na+, K+, ATPase.1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Cardiac glycosides. 6. Gitoxigenin C16 acetates, formates, methoxycarbonates, and digitoxosides. Synthesis and Na+,K+-ATPase inhibitory activities.
AID1570111Cytotoxicity against human BJ cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (13.33)18.7374
1990's4 (26.67)18.2507
2000's4 (26.67)29.6817
2010's2 (13.33)24.3611
2020's3 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.55

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.55 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index5.08 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.55)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies3 (18.75%)4.05%
Observational0 (0.00%)0.25%
Other13 (81.25%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]