Compound: digitoxin
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]7O[C@@H]([C@@H](O[C@@H]8O[C@@H]([C@@H](O)[C@H](C8)O)C)[C@H](C7)O)C)[C@H](C6)O)C)CC5)CC4)C)CC3)CC2)C
InChIKey: WDJUZGPOPHTGOT-XUDUSOBPSA-N
Synonyms: digitoxin, 71-63-6, Digitoxoside, Crystodigin, Carditoxin, Cristapurat, Digitophyllin, Digitoxinum, Unidigin, Cardigin, Digitoksin, Purpurid, Cardidigin, Glucodigin, Lanatoxin, Digitoxina, Digitoxine, Digicor, Digimerck, Digipural, Digitalin, crystalline, tradigal, Asthenthilo, Digitaline, Digitoksim, Digitossina, Digitrin, Mono-glycocard, Digisidin, Digilong, Myodigin, Tardigal, Digitoxigenin-tridigitoxosid, Purodigin, Ditaven, Tri-digitoxoside, Digitaline nativelle, Crystalline digitalin, E90NZP2L9U, Digitoxigenin tridigitoxoside, Digitaline cristallisee, DTXSID0022933, NSC-7529, DTXCID102933, 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one, CHEBI:28544, NSC7529, 3beta-[2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyloxy]-14-hydroxy-5beta-card-20(22)-enolide, Card-20(22)-enolide, 3-((O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14-hydroxy-, (3beta,5beta)-, Card-20(22)-enolide, 3-((O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14-hydroxy-, (3beta,5beta)-, Digitoxin Philo, AWD, Digitoxin, Didier, Digitoxin, 3-((3S,5R,8R,9S,10S,13R,14S,17R)-3-((2R,4S,5S,6R)-5-((2S,4S,5S,6R)-5-((2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl)oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-17-yl)-2H-furan-5-one, 3beta-(2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyloxy)-14-hydroxy-5beta-card-20(22)-enolide, 4-((3S,5R,8R,9S,10S,13R,14S,17R)-3-((2R,4S,5S,6R)-5-((2S,4S,5S,6R)-5-((2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl)oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-17-yl)-5H-furan-2-one, 4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-5H-furan-2-one, Nativelle digitaline, Nativelle, Digitaline, RefChem:5753, C01AA04, CP4071, (3beta,5beta)-3-((O-2,6-Dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14-hydroxycard-20(22)-enolide, 200-760-5, 4-((1S,2S,5S,7R,10R,11S,14R,15R)-5-(((2R,4S,5S,6R)-5-(((2S,4S,5S,6R)-5-(((2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl)oxy)-4-hydroxy-6-methyloxan-2-yl)oxy)-4-hydroxy-6-methyloxan-2-yl)oxy)-11-hydroxy-2,15-dimethyltetracyclo(8.7.0.02,7.011,15)heptadecan-14-yl)-2,5-dihydrofuran-2-one, Crystodigin (TN), DigitoXin, USP, Acedoxin, Coramedan, 1339-93-1, MLS000069787, Digitoxosidum, Carditalin, Digitoxin 100 microg/mL in Acetonitrile, SMR000058529, Monodigitoxoside, Mono-digitoxid, Digitossina [DCIT], NSC 7529, Mono-digitoxid [German], Digitoxine [INN-French], Digitoxinum [INN-Latin], MFCD00003686, Tri-digitoxoside [German], Digitoxina [INN-Spanish], CAS-71-63-6, 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one, Caswell No. 349, Digitoxigenin-tridigitoxosid [German], UNII-E90NZP2L9U, CCRIS 7116, HSDB 215, Digitoxin RS, Digitoxin CRS, Digitoxin [USP:INN:BAN:JAN], NCGC00159428-02, EINECS 200-760-5, Digitoxin (Standard), EPA Pesticide Chemical Code 097002, BRN 0076678, Digitoxin for LC assay, DIGITOXIN [INN], DIGITOXIN [JAN], DIGITOXIN [MI], DIGITOXIN [HSDB], DIGITOXIN [VANDF], DIGITOXINUM [HPUS], DIGITOXIN [USP-RS], DIGITOXIN [WHO-DD], DIGITOXIN [WHO-IP], Digitoxin (JAN/USP/INN), Digitoxin for LC assay CRS, SCHEMBL20940, CHEMBL254219, cid_441207, GTPL6782, MEGxp0_001901, orb1310748, DIGITOXIN [ORANGE BOOK], DIGITOXIN [EP MONOGRAPH], DIGITOXIN [USP IMPURITY], REGID_for_CID_441207, ACon0_000319, ACon1_000610, BDBM46356, HY-B1357R, DIGITOXIN [USP MONOGRAPH], DIGITOXINUM [WHO-IP LATIN], CARD-20(22)-ENOLIDE, 3-((O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-14-HYDROXY-, (3.BETA.,5.BETA.)-, Digoxin EP Impurity A (Digitoxin), HY-B1357, MSK11162, Tox21_111659, Tox21_302269, EBC-13579, LMST01120018, AKOS015915863, Digitoxin, >=92% (HPLC), powder, Tox21_111659_1, CCG-208538, CS-5502, DB01396, OD09336, SMP1_000096, DIGOXIN IMPURITY A [EP IMPURITY], NCGC00094652-06, NCGC00094652-07, NCGC00094652-09, NCGC00142623-02, NCGC00142623-03, NCGC00142623-04, NCGC00142623-05, NCGC00255265-01, 4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-7-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2,5-dihydrofuran-2-one, AS-75726, ST072187, SBI-0051348.P003, D0542, C06955, D00297, D89676, EN300-123649, Q423890, SR-01000721879-2, BRD-K63668566-001-01-7, A572A148-EC30-47D2-A32A-C9D8A93F8EFC, Digitoxin, British Pharmacopoeia (BP) Reference Standard, Z1552200029, Digitoxin, European Pharmacopoeia (EP) Reference Standard, Digitoxin, United States Pharmacopeia (USP) Reference Standard, (3.BETA.,5.BETA.)-3-((O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXAPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-14-HYDROXYCARD-20(22)-ENOLIDE, (3.BETA.,5.BETA.)-3-((O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-14-HYDROXYCARD-20(22)-ENOLIDE, (3b,5b)-3-[(O-2,6-Dideoxy-b-D-ribo-hexapyranosyl-(1->4)-2 ,6-dideoxy-b-D-ribo-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide, (3beta,5beta)-3-{[2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-14-hydroxycard-20(22)-enolide, 3.BETA.-((2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-14-HYDROXY-5.BETA.-CARD-20(22)-ENOLIDE, 3beta-[2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyloxy]-14-hydroxy-5beta-card-20(22)-enolide, 3beta-{[2,6-Dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-14-hydroxy-5beta-card-20(22)-enolide, 4-((1S,2S,5S,11S,7R,10R,14R,15R)-5-{5-[5-((2S,4S,5S,6R)-4,5-dihydroxy-6-methyl (2H-3,4,5,6-tetrahydropyran-2-yloxy))(4S,5S,2R,6R)-4-hydroxy-6-methyl(2H-3,4,5 ,6-tetrahydropyran-2-yloxy)](4S,5S,2R,6R)-, 4-((1S,2S,5S,11S,7R,10R,14R,15R)-5-{5-[5-((2S,4S,5S,6R)-4,5-dihydroxy-6-methyl (2H-3,4,5,6-tetrahydropyran-2-yloxy))(4S,5S,2R,6R)-4-hydroxy-6-methyl(2H-3,4,5 ,6-tetrahydropyran-2-yloxy)](4S,5S,2R,6R)-4-hydroxy-6-methyl(2H-3,4,5,6-tetrah ydropyran-2-yloxy), 4-((3S,5R,8R,9S,10S,13R,14S,17R)-3-(((2R,4S,5S,6R)-5-(((2S,4S,5S,6R)-5-(((2S,4S,5S,6R)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one, 4-hydroxy-6-methyl(2H-3,4,5,6-tetrah ydropyran-2-yloxy)}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0<2,7>.0<11,15>]h eptadec-14-yl)-5-hydrofuran-2-one, Card-20(22)-enolide, 3-((O-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl)oxy)-14-hydroxy-, (3beta,5beta)-, Card-20(22)-enolide, 3-((O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14-hydroxy, (3beta,5beta)-, Card-20(22)-enolide, 3-((O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1.fwdarw.4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1.fwdarw.4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14-hydroxy-, (3beta,5beta)-
Theoretical properties:
molecular_formula: C41H64O13
molecular_weight: 764.9 g/mol
exact_mass: 764.43469209 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 13
rotatable_bond_count: 7
heavy_atom_count: 54
topological_polar_surface_area: 183 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Very small elongated, rectangular plates from dilute alcohol
color: Very small elongated, rectangular plates from dilute alcohol
odor: Odorless
melting_point: 493 to 495 °F when anhydrous (EPA, 1998)
Descriptions:
pubchem: Digitoxin is a cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(14)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(14)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain. It has a role as an EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor. It is functionally related to a digitoxigenin. It is a conjugate acid of a digitoxin(1-).
chebi: A cardenolide glycoside in which the 3β-hydroxy group of digitoxigenin carries a 2,6-dideoxy-β-<small>D</small>-<i>ribo</i>-hexopyranosyl-(1→4)-2,6-dideoxy-β-<small>D</small>-<i>ribo</i>-hexopyranosyl-(1→4)-2,6-dideoxy-β-<small>D</small>-<i>ribo</i>-hexopyranosyl trisaccharide chain.
chembl: DIGITOXIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Digitoxin is a cardiac glycoside used for the treatment of heart failure and certain kinds of heart arrhythmia. It is a phytosteroid and is similar in structure and effects to digoxin, though the effects are longer-lasting. Unlike digoxin, which is eliminated from the body via the kidneys, it is eliminated via the liver, and so can be used in patients with poor or erratic kidney function. While several controlled trials have shown digoxin to be effective in a proportion of patients treated for heart failure, the evidence base for digitoxin is not as strong, although it is presumed to be similarly effective.