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OLEANDRIN

CAS No.:
465-16-7
Catalog Number:
AG00DBB2
Molecular Formula:
C32H48O9
Molecular Weight:
576.7181
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
2mg
99%
1 week
United States
$357
- +
5mg
99%
1 week
United States
$523
- +
10mg
99%
1 week
United States
$857
- +
25mg
99%
1 week
United States
$1473
- +
Product Description
Catalog Number:
AG00DBB2
Chemical Name:
OLEANDRIN
CAS Number:
465-16-7
Molecular Formula:
C32H48O9
Molecular Weight:
576.7181
MDL Number:
MFCD26960889
IUPAC Name:
[(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
InChI:
InChI=1S/C32H48O9/c1-17-29(35)24(37-5)14-27(39-17)41-21-8-10-30(3)20(13-21)6-7-23-22(30)9-11-31(4)28(19-12-26(34)38-16-19)25(40-18(2)33)15-32(23,31)36/h12,17,20-25,27-29,35-36H,6-11,13-16H2,1-5H3/t17-,20+,21-,22-,23+,24-,25-,27-,28-,29-,30-,31+,32-/m0/s1
InChI Key:
JLPDBLFIVFSOCC-XYXFTTADSA-N
SMILES:
CO[C@H]1C[C@H](O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]2[C@@H]3CC[C@]3([C@]2(O)C[C@@H]([C@@H]3C2=CC(=O)OC2)OC(=O)C)C)C)O[C@H]([C@@H]1O)C
EC Number:
207-361-5
UNII:
II95UDU7I4
Properties
Complexity:
1080  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
13  
Defined Bond Stereocenter Count:
0
Exact Mass:
576.33g/mol
Formal Charge:
0
Heavy Atom Count:
41  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
576.727g/mol
Monoisotopic Mass:
576.33g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
121A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.4  
Literature
Title Journal
Identification of anti-viral activity of the cardenolides, Na(+)/K(+)-ATPase inhibitors, against porcine transmissible gastroenteritis virus. Toxicology and applied pharmacology 20171001
Short-term exposure to oleandrin enhances responses to IL-8 by increasing cell surface IL-8 receptors. British journal of pharmacology 20140701
Flavonoid and cardenolide glycosides and a pentacyclic triterpene from the leaves of Nerium oleander and evaluation of cytotoxicity. Phytochemistry 20120501
[A non-fatal Nerium oleander self-poisoning: case report and discussion]. Annales de cardiologie et d'angeiologie 20120401
Unexpected double lethal oleander poisoning. The American journal of forensic medicine and pathology 20120301
'The Lower Threshold' phenomenon in tumor cells toward endogenous digitalis-like compounds: Responsible for tumorigenesis? Journal of carcinogenesis 20120101
Autophagic cell death is induced by acetone and ethyl acetate extracts from Eupatorium odoratum in vitro: effects on MCF-7 and vero cell lines. TheScientificWorldJournal 20120101
Radiation, inflammation, and immune responses in cancer. Frontiers in oncology 20120101
In vitro and in vivo neuroprotective activity of the cardiac glycoside oleandrin from Nerium oleander in brain slice-based stroke models. Journal of neurochemistry 20111101
Ex vivo activity of cardiac glycosides in acute leukaemia. PloS one 20110101
Rapid detection of oleander poisoning by Dimension Vista digoxin assay (Flex Reagent Cartridge). Journal of clinical laboratory analysis 20110101
β-Elemene-induced autophagy protects human gastric cancer cells from undergoing apoptosis. BMC cancer 20110101
Concurrent proinflammatory and apoptotic activity of a Helicobacter pylori protein (HP986) points to its role in chronic persistence. PloS one 20110101
Detoxification of Nerium indicum roots based on Indian system of medicine: phytochemical and toxicity evaluations. Acta poloniae pharmaceutica 20110101
Influence of fungal elicitation on glycyrrhizin production in transformed cell cultures of Abrus precatorius Linn. Pharmacognosy magazine 20110101
Targeting inflammatory pathways by triterpenoids for prevention and treatment of cancer. Toxins 20101001
A review of the natural history, toxinology, diagnosis and clinical management of Nerium oleander (common oleander) and Thevetia peruviana (yellow oleander) poisoning. Toxicon : official journal of the International Society on Toxinology 20100901
Na, K-ATPase: Ubiquitous Multifunctional Transmembrane Protein and its Relevance to Various Pathophysiological Conditions. Journal of clinical medicine research 20100201
Human tumor cell sensitivity to oleandrin is dependent on relative expression of Na+, K+ -ATPase subunitst. Journal of experimental therapeutics & oncology 20100101
Acute cardiac toxicity of nerium oleander/indicum poisoning (kaner) poisoning. Heart views : the official journal of the Gulf Heart Association 20100101
A case of non-fatal oleander poisoning. BMJ case reports 20100101
Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs. Journal of natural products 20091101
Oleander intoxication in New World camelids: 12 cases (1995-2006). Journal of the American Veterinary Medical Association 20090801
Oleandrin-mediated inhibition of human tumor cell proliferation: importance of Na,K-ATPase alpha subunits as drug targets. Molecular cancer therapeutics 20090801
In vitro study of the effectiveness of three commercial adsorbents for binding oleander toxins. Clinical toxicology (Philadelphia, Pa.) 20090301
Cancer is a preventable disease that requires major lifestyle changes. Pharmaceutical research 20080901
The inhibitory effect of quercitrin gallate on iNOS expression induced by lipopolysaccharide in Balb/c mice. Journal of veterinary science 20080901
A fatal case of oleandrin poisoning. Forensic science international 20080806
Nucleolus and c-Myc: potential targets of cardenolide-mediated antitumor activity. Molecular cancer therapeutics 20080501
Rapid detection of oleander poisoning by Digoxin III, a new Digoxin assay: impact on serum Digoxin measurement. American journal of clinical pathology 20080401
The prince and the pauper. A tale of anticancer targeted agents. Molecular cancer 20080101
Determinants of human and mouse melanoma cell sensitivities to oleandrin. Journal of experimental therapeutics & oncology 20080101
Autophagic cell death of human pancreatic tumor cells mediated by oleandrin, a lipid-soluble cardiac glycoside. Integrative cancer therapies 20071201
Stability of oleander extract and oleandrin in sera stored in plastic serum separator tubes. Annals of clinical biochemistry 20070901
Endogenous and exogenous cardiac glycosides: their roles in hypertension, salt metabolism, and cell growth. American journal of physiology. Cell physiology 20070801
Oleandrin produces changes in intracellular calcium levels in isolated cardiomyocytes: a real-time fluorescence imaging study comparing adult to neonatal cardiomyocytes. Journal of toxicology and environmental health. Part A 20070315
Oleandrin induces apoptosis in human, but not in murine cells: dephosphorylation of Akt, expression of FasL, and alteration of membrane fluidity. Molecular immunology 20070301
Cardiac glycoside induces cell death via FasL by activating calcineurin and NF-AT, but apoptosis initially proceeds through activation of caspases. Apoptosis : an international journal on programmed cell death 20070201
Topical administration of oleandrin could protect against gentamicin ototoxicity via inhibition of activator protein-1 and c-Jun N-terminal kinase. Medical hypotheses 20070101
Nerium oleander (Oleandrin). Journal of the Society for Integrative Oncology 20070101
Naturally occurring NF-kappaB inhibitors. Mini reviews in medicinal chemistry 20060801
Oleandrin-mediated expression of Fas potentiates apoptosis in tumor cells. Journal of clinical immunology 20060701
Cardiac glycosides initiate Apo2L/TRAIL-induced apoptosis in non-small cell lung cancer cells by up-regulation of death receptors 4 and 5. Cancer research 20060601
Cardiac glycoside inhibits IL-8-induced biological responses by downregulating IL-8 receptors through altering membrane fluidity. Journal of cellular physiology 20060401
The new enzyme-linked immunosorbent digoxin assay on the ADVIA Integrated Modular System is virtually free from oleander interference. Therapeutic drug monitoring 20060401
Oleandrin-mediated oxidative stress in human melanoma cells. Journal of experimental therapeutics & oncology 20060101
Unexpectedly dangerous escargot stew: oleandrin poisoning through the alimentary chain. Journal of analytical toxicology 20060101
Cytotoxic effects of leaf, stem and root extracts of Nerium oleander on leukemia cell lines and role of the p-glycoprotein in this effect. Journal of experimental therapeutics & oncology 20060101
A non-fatal oleander poisoning. International journal of legal medicine 20050701
Determination of oleandrin in tissues and biological fluids by liquid chromatography-electrospray tandem mass spectrometry. Journal of agricultural and food chemistry 20050601
Chemosensitization and radiosensitization of tumors by plant polyphenols. Antioxidants & redox signaling 20050101
Rapid detection of oleander poisoning using digoxin immunoassays: comparison of five assays. Therapeutic drug monitoring 20041201
A rare cause of complete heart block after transdermal botanical treatment for psoriasis. Pacing and clinical electrophysiology : PACE 20041201
Toxic and sub-lethal effects of oleandrin on biochemical parameters of fresh water air breathing murrel, Channa punctatus (Bloch.). Indian journal of experimental biology 20040401
Inhibition of 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion markers in CD-1 mouse skin by oleandrin. Toxicology and applied pharmacology 20040315
Oleandrin suppresses activation of nuclear transcription factor-kappa B and activator protein-1 and potentiates apoptosis induced by ceramide. Biochemical pharmacology 20031201
A rapid and sensitive LC/MS/MS assay for quantitative determination of digoxin in rat plasma. Journal of pharmaceutical and biomedical analysis 20030821
Toxic potential of oleander derived compost and vegetables grown with oleander soil amendments. Veterinary and human toxicology 20030801
Activated charcoal is effective but equilibrium dialysis is ineffective in removing oleander leaf extract and oleandrin from human serum: monitoring the effect by measuring apparent digoxin concentration. Therapeutic drug monitoring 20030601
Enhancement of radiotherapy by oleandrin is a caspase-3 dependent process. Cancer letters 20021128
Determination of bovine blood oleandrin by high-performance liquid chromatography and postcolumn derivatization. Journal of chromatographic science 20021001
Simultaneous determination of cardenolides by sonic spray ionization liquid chromatography-ion trap mass spectrometry--a fatal case of oleander poisoning. Journal of analytical toxicology 20020101
Murine pharmacokinetics and metabolism of oleandrin, a cytotoxic component of Nerium oleander. Journal of experimental therapeutics & oncology 20020101
Inhibition of export of fibroblast growth factor-2 (FGF-2) from the prostate cancer cell lines PC3 and DU145 by Anvirzel and its cardiac glycoside component, oleandrin. Biochemical pharmacology 20010815
Properties