Compound: ouabain
SMILES: O=C1OCC(=C1)[C@@H]2[C@@]3([C@@](O)([C@H]4[C@@H]([C@@]5([C@@](O)(C[C@@H](O[C@@H]6O[C@H]([C@H](O)[C@H]([C@H]6O)O)C)C[C@H]5O)CC4)CO)[C@@H](C3)O)CC2)C
InChIKey: LPMXVESGRSUGHW-HBYQJFLCSA-N
Synonyms: ouabain, Ouabaine, Astrobain, Gratibain, Gratus strophanthin, Uabanin, Purostrophan, Acocantherin, Ouabagenin L-rhamnoside, Oubain, Ouabain anhydrous, Strophoperm, Quabain, 630-60-4, Strophalen, Uabaina, Ouabagenin-L-rhamnosid, Strophantin-g, Rectobaina, Solufantina, Strophosan, G-Strophicor, Strophanthin G, DTXSID0043765, NSC-25485, CHEBI:472805, 5ACL011P69, DTXCID8023765, Card-20(22)-enolide, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-1,5,11,14,19-pentahydroxy-, (1beta,3beta,5beta,11alpha)-, 3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-1,5,11alpha,14,19-pentahydroxycard-20(22)-enolide, 3-(alpha-L-rhamnopyranosyloxy)-1beta,5beta,11alpha,14,19-pentahydroxy-5beta-card-20(22)-enolide, G Strophanthin, 3-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one, 4-[(1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one, NSC-757425, Ouabaine arnaud, 3-((1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-17-yl)-2H-furan-5-one, 4-((1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)tetracyclo(8.7.0.0^(2,7).0^(11,15))heptadecan-14-yl)-2,5-dihydrofuran-2-one, RefChem:928329, (1beta,3beta,5beta,11alpha)-3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-1,5,11,14,19-pentahydroxycard-20(22)-enolide, 211-139-3, 4-((1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)tetracyclo(8.7.0.02,7.011,15)heptadecan-14-yl)-2,5-dihydrofuran-2-one, Acocantherin octahydrate, G-Strophanthin, Acocantherine, Kombetin, Strodival, Cardiac glycoside, MLS000069786, CHEMBL222863, SMR000058492, Strophanthin-G, Card-20(22)-enolide, 3-[(6-deoxy-.alpha.-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxy-, (1.beta.,3.beta.,5.beta.,11.alpha.)-, OBN, Ouabain, Octahydrate, G-STROPHANTHIN [JAN], Ouabain - anhydrous, CAS-630-60-4, Ouabagenin-L-rhamnosid [German], SR-01000076047, CCRIS 965, UNII-5ACL011P69, HSDB 3519, 1ibg, NCGC00163473-01, 3-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one, CARD-20(22)-ENOLIDE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-1,5,11,14,19-PENTAHYDROXY-, (1.BETA.,3.BETA.,5.BETA.,11.ALPHA.)-, EINECS 211-139-3, NSC 25485, BRN 0101712, 3a3y, Opera_ID_395, OUABAIN [MI], 4-[5-((6S,2R,3R,4R,5R)-3,4,5-trihydroxy-6-methyl(2H-3,4,5,6-tetrahydropyran-2- yloxy))(1S,5S,7S,11S,2R,3R,10R,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxym ethyl)-15-methyltetracyclo[8.7.0.0<2,7>.0<, OUABAIN [MART.], Prestwick0_000471, Prestwick1_000471, Prestwick2_000471, Prestwick3_000471, OUABAIN [WHO-DD], Epitope ID:161502, O 3125, G-STROPHANTHIN [MI], Lopac0_000943, SCHEMBL15433, BSPBio_000602, 5-18-05-00625 (Beilstein Handbook Reference), SPBio_002541, OUABAIN [EP MONOGRAPH], BPBio1_000664, cid_439501, GTPL4826, OUABAIN ANHYDROUS [HSDB], REGID_for_CID_439501, 3n23, HMS2089J19, HMS2235A07, HMS3262N08, Tox21_110024, Tox21_112057, Tox21_301547, Tox21_500943, BDBM50286739, EBC-27354, HB1140, AKOS024285581, Tox21_112057_1, CCG-205024, CCG-208243, DB01092, LP00943, MO34347, SDCCGSBI-0050917.P002, 3-(6-Deoxy-alpha-L-mannopyranosyloxy)-1,5,11a,14,19-pentahydroxycard-20(22)-enolide, SMP1_000142, NCGC00013319-01, NCGC00015769-02, NCGC00015769-13, NCGC00015769-17, NCGC00015769-30, NCGC00015769-32, NCGC00017394-02, NCGC00017394-07, NCGC00017394-11, NCGC00255970-01, NCGC00261628-01, NCGC00263656-01, 3beta-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-1beta,5,11alpha,14,19-pentahydroxy-5beta-card-20(22)-enolide, 4-[(1R,3aS,3bR,5aS,7S,9R,9aR,9bS,10R,11aR)-3a,5a,9,10-tetrahydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2,5-dihydrofuran-2-one, ST085767, EU-0100943, NS00003260, C01443, 11,15>]heptadec-14-yl]-5-hydrofuran- 2-one, EN300-19631221, Q285911, SR-01000721848, SR-01000076047-1, SR-01000076047-5, SR-01000721848-2, SR-01000721848-4, BRD-K35708212-331-03-1, (1.BETA.,3.BETA.,5.BETA.,11.ALPHA.)-3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-1,5,11,14,19-PENTAHYDROXYCARD-20(22)-ENOLIDE, (1alpha,3beta,5beta,11alpha,17alpha)-3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxycard-20(22)-enolide, 3-[(6-Deoxy-.alpha.-L-mannopyranosyl)oxy]-1,5,11.alpha.,14,19-pentahydroxycard-20(22)-enolide, 4-((1R,3S,5S,8R,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-2H-pyran-2-yloxy)-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one, 4-((1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one, 4-((1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-2H-pyran-2-yloxy)-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one, 4-[(1R,3S,5S,10R,11R,13R,14S,17R)-1,5,11,14-Tetrahydroxy-10-hydroxymethyl-13-methyl-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one, 4-[(R)-1,5,11,14-Tetrahydroxy-10-hydroxymethyl-13-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one, 4-[1,5,11,14-Tetrahydroxy-10-hydroxymethyl-13-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one, 4-[1,5,11,14-Tetrahydroxy-10-hydroxymethyl-13-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one(Ouabain), Ouabain4-[1,5,11,14-Tetrahydroxy-10-hydroxymethyl-13-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one
Theoretical properties:
molecular_formula: C29H44O12
molecular_weight: 584.7 g/mol
exact_mass: 584.28327683 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 8
hydrogen_bond_acceptor_count: 12
rotatable_bond_count: 4
heavy_atom_count: 41
topological_polar_surface_area: 207 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from water
color: Crystals from water
melting_point: 392 °F (EPA, 1998)
Descriptions:
{"pubchem": "Ouabain is a steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na+/K+-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus. It has a role as an anti-arrhythmia drug, a cardiotonic drug, an EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor, an ion transport inhibitor, an EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor, a plant metabolite, an EC 2.3.3.1 [citrate (Si)-synthase] inhibitor and an EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor. It is an 11alpha-hydroxy steroid, a steroid hormone, an alpha-L-rhamnoside, a 14beta-hydroxy steroid, a cardenolide glycoside and a 5beta-hydroxy steroid. It is a conjugate acid of an ouabain(1-).", "chebi": "A steroid hormone that is a multi-hydroxylated \u03b1-<small>L</small>-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na<small><sup>+</small></sup>/K<small><sup>+</small></sup>-ATPase (sodium pump). It has been isolated naturally from <em>Strophanthus gratus </em>.", "chembl": "OUABAIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase -1.0.", "wikipedia": "Ouabain  or  (from Somali waabaayo, \"arrow poison\" through French ouaba\u00efo) also known as g-strophanthin, is a plant derived toxic substance that was traditionally used as an arrow poison in eastern Africa for both hunting and warfare. Ouabain is a cardiac glycoside and, in lower doses, can be used medically to treat hypotension and some arrhythmias. It acts by inhibiting the Na/K-ATPase, also known as the sodium\u2013potassium ion pump. However, adaptations to the alpha-subunit of the Na+/K+-ATPase via amino acid substitutions, have been observed in certain species, namely some herbivore insect species, that have resulted in toxin resistance.\nIt is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities."}