oleandrin: structure
oleandrin : A steroid saponin that consists of oleandrigenin having a 2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl residue attached to the oxygen function at position 3.
ID Source | ID |
---|---|
PubMed CID | 11541511 |
CHEMBL ID | 4285883 |
CHEBI ID | 59030 |
SCHEMBL ID | 25049 |
MeSH ID | M0075525 |
Synonym |
---|
(3beta,5beta,16beta)-16-acetoxy-3-[(2,6-dideoxy-3-o-methyl-alpha-l-arabino-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide |
oleandrina |
CHEBI:59030 , |
465-16-7 |
oleandrin |
neriol |
neriolin |
corrigen |
foliandrin |
folinerin |
neriostene |
oleandrine |
einecs 207-361-5 |
oleandrina [spanish] |
(3beta,16beta)-16-(acetyloxy)-3-((2,6-dideoxy-3-o-methyl-l-arabino-hexopyranosyl)oxy)-14-hydroxy card-20(22)-enolide |
hsdb 3518 |
16beta-acetoxy-3beta-(2,6-dideoxy-3-o-methyl-l-arabino-hexopyranosyloxy)-14-hydroxycard-20(22)-enolide |
nsc 692219 |
card-20(22)-enolide, 16-(acetyloxy)-3-((2,6-dideoxy-3-o-methyl-alpha-l-arabino-hexopyranosyl)oxy)-14-hydroxy-, (3-beta,5-beta,16-beta)- |
card-20(22)-enolide, 16-(acetyloxy)-3-((2,6-dideoxy-3-o-methyl-alpha-l-arabino-hexopyranosyl)oxy)-14-hydroxy-, (3beta,5beta,16beta)- |
16beta-(acetyloxy)-3beta-((2,6-dideoxy-3-o-methyl-l-arabino-hexopyranosyl)oxy)-14-hydroxycard-20-(22)-enolide |
nsc-692219 |
ii95udu7i4 , |
unii-ii95udu7i4 |
C19987 |
oleandrin [who-dd] |
card-20(22)-enolide, 16-(acetyloxy)-3-((2,6-dideoxy-3-o-methyl-.alpha.-l-arabino-hexopyranosyl)oxy)-14-hydroxy-, (3.beta.,5.beta.,16.beta.)- |
oleandrin [mi] |
anvirzel |
S6918 |
SCHEMBL25049 |
(3 beta,16 beta)-16-(acetyloxy)-3-((2,6-dideoxy-3-o-methyl-l-arabino-hexopyranosyl)oxy)-14-hydroxy card-20(22)-enolide |
HY-13719 |
CS-5505 |
AKOS032430539 |
oleandrigenin oleandroside |
folinevin |
dtxcid401474666 |
(3beta,5beta,16beta)-16-acetoxy-3-((2,6-dideoxy-3-o-methyl-alpha-l-arabino-hexopyranosyl)oxy)-14-hydroxycard-20(22)-enolide |
(3beta,5beta,16beta)-16-(acetyloxy)-3- |
oleandrin, >=98% (hplc) |
pbi-05204 |
pbi 05204 |
1315607-79-4 |
DB12843 |
[(3s,5r,8r,9s,10s,13r,14s,16s,17r)-14-hydroxy-3-[(2r,4s,5s,6s)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-17-(5-oxo-2h-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate |
[(3s,8r,9s,10s,13r,14s,16s,17r)-14-hydroxy-3-[(4s,5s,6s)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-17-(5-oxo-2h-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate |
Q411532 |
DTXSID40861950 , |
CHEMBL4285883 |
MS-30375 |
bdbm50465465 |
oleandrin (pbi-05204) |
pbi-05204 (mixture of botanical compounds) |
gtpl12618 |
pbi05204 |
Oleandrin is a monomeric compound extracted from leaves and seeds of Nerium oleander.
Excerpt | Reference | Relevance |
---|---|---|
"Oleandrin is a cardiac glycoside obtained from of N." | ( Glycoside oleandrin downregulates toll-like receptor pathway genes and associated miRNAs in human melanoma cells. Dodurga, Y; Elmas, L; Eroğlu Güneş, C; Kurar, E; Seçer Çelik, F; Seçme, M, 2022) | 1.85 |
"Oleandrin is a monomeric compound extracted from leaves and seeds of Nerium oleander. " | ( Oleandrin induces DNA damage responses in cancer cells by suppressing the expression of Rad51. Bao, Z; Chen, Z; Feng, H; Li, W; Liang, Y; Shen, H; Tian, B; Wang, X; Ying, S, 2016) | 3.32 |
Oleandrin treatment resulted in selective inhibition of human cancer cell growth but not rodent cell proliferation. Treatment also induced the phosphorylation of PERK and eIF2α.
Excerpt | Reference | Relevance |
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"Nerium oleander (No), is a toxic plant." | ( Cytotoxic effects of leaf, stem and root extracts of Nerium oleander on leukemia cell lines and role of the p-glycoprotein in this effect. Akgün-Dar, K; Atasever, B; Carin, M; Kiliçaslan-Ayna, T; Kuruca, SE; Meriçli, F; Seyhan, VG; Turan, N, 2006) | 0.33 |
" Grade ≥ 3 treatment-emergent adverse events occurred in 63." | ( A Phase II, Single-Arm, Open-Label, Bayesian Adaptive Efficacy and Safety Study of PBI-05204 in Patients with Stage IV Metastatic Pancreatic Adenocarcinoma. Berlin, J; Borazanci, EH; Cardin, DB; Newman, RA; Picozzi, VJ; Rosemury, A; Roth, MT; Steinbach, M; Wadlow, RC, 2020) | 0.56 |
Excerpt | Reference | Relevance |
---|---|---|
" Oleandrin was rapidly absorbed after oral dosing (Cmax at 20 min) although the elimination half-life was longer (2." | ( Murine pharmacokinetics and metabolism of oleandrin, a cytotoxic component of Nerium oleander. Felix, E; Ho, DH; Johansen, M; Madden, TL; Newman, RA; Ni, D, ) | 1.31 |
Excerpt | Reference | Relevance |
---|---|---|
" Selected cardiac glycosides were tested in combination with four clinically relevant cytotoxic drugs (5-fluorouracil, oxaliplatin, cisplatin, irinotecan)." | ( Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs. Bohlin, L; Felth, J; Fryknäs, M; Gullbo, J; Lindskog, M; Rickardson, L; Rosén, J; Wickström, M, 2009) | 0.35 |
"In the majority of the cell lines tested, lower concentrations of Anvirzel™ induced a synergistic effect when combined with low concentrations of Cisplatin after an incubation period of 48 to 72 h." | ( Anvirzel™ in combination with cisplatin in breast, colon, lung, prostate, melanoma and pancreatic cancer cell lines. Apostolou, P; Chatziioannou, M; Ioannou, E; Knocke, DR; Komiotis, D; Nester, J; Papasotiriou, I; Toloudi, M, 2013) | 0.39 |
Excerpt | Reference | Relevance |
---|---|---|
"h/ml), respectively, resulting in an oral bioavailability of approximately 30%." | ( Murine pharmacokinetics and metabolism of oleandrin, a cytotoxic component of Nerium oleander. Felix, E; Ho, DH; Johansen, M; Madden, TL; Newman, RA; Ni, D, ) | 0.4 |
Oleandrin, ouabain, and digoxin in the used dosage do not present therapeutic potential for the treatment of congestive heart failure.
Excerpt | Relevance | Reference |
---|---|---|
" Oleandrin was rapidly absorbed after oral dosing (Cmax at 20 min) although the elimination half-life was longer (2." | ( Murine pharmacokinetics and metabolism of oleandrin, a cytotoxic component of Nerium oleander. Felix, E; Ho, DH; Johansen, M; Madden, TL; Newman, RA; Ni, D, ) | 1.31 |
" It is concluded that the glycosides oleandrin, ouabain, and digoxin in the used dosage do not present therapeutic potential for the treatment of congestive heart failure caused by doxorubicin." | ( Comparative Therapeutic Potential of Cardioactive Glycosides in Doxorubicin Model of Heart Failure. Botelho, AFM; Canta, GN; da Cruz, JPO; da Silva Ferreira, R; Fernandes, PBU; Lempek, MR; Mantovani, MM; Melo, MM; Silva, FLA; Veado, JCC, 2022) | 0.99 |
Class | Description |
---|---|
cardenolide glycoside | Any member of the class of cardenolides with glycosyl residues attached to position 3. |
14beta-hydroxy steroid | A 14-hydroxy steroid in which the hydroxy group has a beta-configuration. |
steroid ester | |
steroid saponin | Any saponin derived from a hydroxysteroid. |
[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 | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Neurogenic locus notch homolog protein 1 | Mus musculus (house mouse) | IC50 (µMol) | 0.1200 | 0.1200 | 0.1200 | 0.1200 | AID1410576 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Process | via Protein(s) | Taxonomy |
---|---|---|
Golgi membrane | Neurogenic locus notch homolog protein 1 | Mus musculus (house mouse) |
extracellular region | Neurogenic locus notch homolog protein 1 | Mus musculus (house mouse) |
nucleoplasm | Neurogenic locus notch homolog protein 1 | Mus musculus (house mouse) |
endoplasmic reticulum membrane | Neurogenic locus notch homolog protein 1 | Mus musculus (house mouse) |
cytosol | Neurogenic locus notch homolog protein 1 | Mus musculus (house mouse) |
plasma membrane | Neurogenic locus notch homolog protein 1 | Mus musculus (house mouse) |
endosome membrane | Neurogenic locus notch homolog protein 1 | Mus musculus (house mouse) |
[Information is prepared from geneontology information from the June-17-2024 release] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1570107 | Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay | |||
AID1570125 | Inhibition of porcine kidney Na+/K+-ATPase at 50 uM preincubated for 2 mins followed by ATP addition and measured after 6 mins by bagin-sky assay relative to Olean-drigenin | |||
AID1410589 | Inhibition of doxycycline-induced recombinant mouse N-terminal FLAG-tagged Notch1 (1704 to 2531 residues) activation expressed in human LS174T cells assessed as reduction in NCID expression after 12 hrs by Western blot analysis | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1410584 | Cytotoxicity against human HPBALL cells after 72 hrs by alamar blue dye based fluorescence assay | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1410590 | Inhibition of doxycycline-induced recombinant mouse N-terminal FLAG-tagged Notch1 (1704 to 2531 residues) activation expressed in human LS174T cells assessed as reduction in NCID expression at 0.5 uM after 12 hrs in presence of proteasome inhibitor MG132 | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1410577 | Effect on Notch1 mRNA expression in human HPBALL cells at 0.1 to 0.5 uM measured after 12 hrs | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1410579 | Down regulation of Notch1 expression in human HPBALL cells at 0.5 uM after 12 hrs by Western blot analysis | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1410585 | Down regulation of Notch1 expression in human HPBALL cells at 0.5 uM after 12 hrs in presence of proteasome inhibitor MG132 by Western blot analysis | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1410578 | Inhibition of Notch1 in human HPBALL cells assessed as reduction in NICD expression at 0.5 uM after 12 hrs in presence of proteasome inhibitor MG132 by Western blot analysis | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1410576 | Inhibition of recombinant mouse N-terminal FLAG-tagged Notch1 (1704 to 2531 residues) expressed in human LS174T cells assessed as reduction in doxycycline-induced NICD expression after 12 hrs by Bright-Glo luciferase reporter gene assay | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1410582 | Inhibition of Notch1 in human HPBALL cells assessed as reduction in NICD expression after 72 hrs by Western blot analysis | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1410580 | Inhibition of Notch1 in human HPBALL cells assessed as reduction in HES1 expression after 72 hrs by Western blot analysis | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1740504 | Cytotoxicity against human BJ cells assessed as reduction in cell viability incubated for 72 hrs by resazurin assay | |||
AID1570110 | Antiproliferative activity against human Hep3B cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay | |||
AID1410588 | Inhibition of doxycycline-induced Notch1 (1704 to 2531 residues) expression in human LS174T cells after 12 hrs by Western blot analysis | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1410587 | Inhibition of doxycycline-induced recombinant mouse N-terminal FLAG-tagged Notch1 (1704 to 2531 residues) activation expressed in human LS174T cells assessed as reduction in Hes5 level at 0.05 to 0.3 uM after 12 hrs by Western blot analysis | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1740503 | Cytotoxicity against human HeLa cells assessed as reduction in cell viability incubated for 72 hrs by resazurin assay | |||
AID1410581 | Inhibition of Notch1 in human HPBALL cells assessed as reduction in NICD expression at 0.5 uM after 12 hrs by Western blot analysis | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1740501 | Cytotoxicity against human CEM cells assessed as reduction in cell viability incubated for 72 hrs by resazurin assay | |||
AID1570112 | Inhibition 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 | |||
AID1740502 | Cytotoxicity against human MCF7 cells assessed as reduction in cell viability incubated for 72 hrs by resazurin assay | |||
AID1410583 | Cytotoxicity against HEK293 cells after 72 hrs by fluorescence assay | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1740505 | Inhibition 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%) | |||
AID1570109 | Antiproliferative activity against human A2780 cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay | |||
AID1570111 | Cytotoxicity against human BJ cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay | |||
AID1410586 | Inhibition of doxycycline-induced recombinant mouse N-terminal FLAG-tagged Notch1 (1704 to 2531 residues) activation expressed in human LS174T cells assessed as reduction in Hes1 level at 0.05 to 0.3 uM after 12 hrs by Western blot analysis | 2018 | Journal of natural products, 05-25, Volume: 81, Issue:5 | The Notch Inhibitors Isolated from Nerium indicum. |
AID1570106 | Antiproliferative activity against human CEM cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay | |||
AID1570108 | Antiproliferative activity against human HeLa cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay | |||
AID1159550 | Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening | 2015 | Nature cell biology, Nov, Volume: 17, Issue:11 | 6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 7 (6.80) | 18.7374 |
1990's | 12 (11.65) | 18.2507 |
2000's | 35 (33.98) | 29.6817 |
2010's | 30 (29.13) | 24.3611 |
2020's | 19 (18.45) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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 strong demand-to-supply ratio for research on this compound.
| This Compound (48.53) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 3 (2.80%) | 5.53% |
Reviews | 5 (4.67%) | 6.00% |
Case Studies | 17 (15.89%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 82 (76.64%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |