Compound: OLEANDRIN
SMILES: O=C1OCC(=C1)[C@@H]2[C@@]3([C@@](O)([C@H]4[C@@H]([C@@]5([C@@H](C[C@@H](O[C@@H]6O[C@H]([C@H](O)[C@H](C6)OC)C)CC5)CC4)C)CC3)C[C@@H]2OC(=O)C)C
InChIKey: JLPDBLFIVFSOCC-XYXFTTADSA-N
Synonyms: OLEANDRIN, 465-16-7, Foliandrin, Neriolin, Folinerin, Neriostene, Oleandrina, Oleandrine, Neriol, II95UDU7I4, NSC-692219, [(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, CHEBI:59030, Card-20(22)-enolide, 16-(acetyloxy)-3-((2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy)-14-hydroxy-, (3beta,5beta,16beta)-, DTXSID40861950, (3beta,5beta,16beta)-16-acetoxy-3-[(2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide, ((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, (3beta,5beta,16beta)-16-acetoxy-3-((2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy)-14-hydroxycard-20(22)-enolide, RefChem:44190, DTXCID401474666, (3 beta,16 beta)-16-(acetyloxy)-3-((2,6-dideoxy-3-O-methyl-L-arabino-hexopyranosyl)oxy)-14-hydroxy card-20(22)-enolide, (1S,2S,5S,7R,10R,11S,13S,14R,15R)-11-hydroxy-5-((5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy)-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo(8.7.0.02,7.011,15)heptadecan-13-yl acetate, 207-361-5, Corrigen, Anvirzel, C32H48O9, PBI 05204, PBI-05204, [(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, 1315607-79-4, Oleandrina [Spanish], UNII-II95UDU7I4, HSDB 3518, EINECS 207-361-5, Oleandrin (Standard), NSC 692219, OLEANDRIN [MI], enanthren-16-yl acetate, OLEANDRIN [WHO-DD], SCHEMBL25049, Oleandrin (PBI-05204), orb1301315, orb3140431, CHEMBL4285883, Oleandrin, >=98% (HPLC), GTPL12618, JLPDBLFIVFSOCC-XYXFTTADSA-N, GLXC-10398, PBI05204, BDBM50465465, HY-13719R, MSK162607, s6918, STL565781, AKOS032430539, CS-5505, DB12843, EBC-106021, MO26544, (1R,2S,3aS,3bR,5aR,7S,9aS,9bS,11aR)-3a-hydroxy-7-{[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-1-(5-oxo-2,5-dihydrofuran-3-yl)-hexadecahydro-1H-cyclopenta[a]phenanthren-2-yl acetate, 16beta-(Acetyloxy)-3beta-((2,6-dideoxy-3-O-methyl-L-arabino-hexopyranosyl)oxy)-14-hydroxycard-20-(22)-enolide, 16beta-Acetoxy-3beta-(2,6-dideoxy-3-O-methyl-L-arabino-hexopyranosyloxy)-14-hydroxycard-20(22)-enolide, DA-56415, HY-13719, MS-30375, PBI-05204 (mixture of botanical compounds), C19987, Q411532, BRD-K98006098-001-01-6, 5?\,20(22)-Cardenolide-3?, Corrigen, Foliandrin, Folinerin, Neriol, Neriolin, Neriostene, (3?,5?,16?)-16-(Acetyloxy)-3-[(2,6-dideoxy-3-O-methyl-?-L-arabino-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide, (3beta,16beta)-16-(Acetyloxy)-3-((2,6-dideoxy-3-O-methyl-L-arabino-hexopyranosyl)oxy)-14-hydroxy card-20(22)-enolide, (3beta,5beta,16beta)-16-(acetyloxy)-3-[(2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide, (3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-(((2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-10,13-dimethyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]ph, [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyl-tetrahydropyran-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, 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-, (3-beta,5-beta,16-beta)-
Theoretical properties:
molecular_formula: C32H48O9
molecular_weight: 576.7 g/mol
exact_mass: 576.32983310 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 6
heavy_atom_count: 41
topological_polar_surface_area: 121 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from ethanol
color: Crystals from ethanol
melting_point: 250 °C
solubility: Practically insoluble in water
Descriptions:
pubchem: Oleandrin is 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. It is a 14beta-hydroxy steroid, a cardenolide glycoside, a steroid ester and a steroid saponin. It is functionally related to an oleandrigenin.
chebi: A steroid saponin that consists of oleandrigenin having a 2,6-dideoxy-3-<em>O</em>-methyl-α-<small>L</small>-<i>arabino</i>-hexopyranosyl residue attached to the oxygen function at position 3.
chembl: OLEANDRIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 1.0.
wikipedia: Oleandrin is a cardiac glycoside found in the poisonous plant oleander (Nerium oleander L.). As a main phytochemical of oleander, oleandrin is associated with the toxicity of oleander sap, and has similar properties to digoxin. Oleandrin and other oleander chemicals are potentially toxic to the heart, liver, and kidneys.
Although oleander has been used in traditional medicine and as a dietary supplement, there is no clinical evidence that oleander and its constituents, including oleandrin, are safe or effective for any therapeutic purpose. Oleandrin is not approved by regulatory agencies as a prescription drug.