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Digitoxin

PubChem CID: 441207

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Compound Synonyms digitoxin, 71-63-6, Digitoxoside, Crystodigin, Digitoxinum, Unidigin, Digitophyllin, Carditoxin, Cristapurat, Digitoksin, Purpurid, Cardidigin, Cardigin, Glucodigin, Lanatoxin, DigitoXin, USP, Digitoxina, Digitoxine, Digicor, Digipural, Digitalis, Digitalin, crystalline, Crystodigin (TN), tradigal, Digitoxosidum, Asthenthilo, Carditalin, Digitaline, Digitoksim, Digitossina, Digitrin, Monodigitoxoside, Mono-digitoxid, Mono-glycocard, Coramedan, Digimerck, Digisidin, Myodigin, Tardigal, Digitoxigenin-tridigitoxosid, Acedoxin, Digilong, Purodigin, Ditaven, Natigal, Caswell No. 349, Tri-digitoxoside, De-Tone, Digitoxine [INN-French], Digitoxinum [INN-Latin], Digitoxina [INN-Spanish], UNII-E90NZP2L9U, Crystalline digitalin, E90NZP2L9U, Digitoxigenin tridigitoxoside, Purodigin, crystalline, Digitaline cristallisee, CCRIS 7116, HSDB 215, DTXSID0022933, CHEBI:28544, NSC 7529, NSC-7529, EINECS 200-760-5, 1339-93-1, EPA Pesticide Chemical Code 097002, BRN 0076678, MLS000069787, 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, Digitoxin [USP:INN:BAN:JAN], Digitoxin 100 microg/mL in Acetonitrile, SMR000058529, Digitoxine (INN-French), Digitoxinum (INN-Latin), Digitoxina (INN-Spanish), DIGITOXIN (USP-RS), DIGITOXIN [USP-RS], 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)-, Digitossina [DCIT], DIGITOXIN (EP MONOGRAPH), DIGITOXIN (USP IMPURITY), DIGITOXIN [EP MONOGRAPH], DIGITOXIN [USP IMPURITY], DIGITOXIN (USP MONOGRAPH), Digitoxin (USP:INN:BAN:JAN), DIGITOXIN [USP MONOGRAPH], NSC7529, Mono-digitoxid [German], Tri-digitoxoside [German], CAS-71-63-6, DIGOXIN IMPURITY A (EP IMPURITY), DIGOXIN IMPURITY A [EP IMPURITY], 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)-, Digitoxigenin-tridigitoxosid [German], NCGC00159428-02, 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, 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-hexopyranosyloxy]-14-hydroxy-5beta-card-20(22)-enolide, MFCD00003686, Digitoxin (Standard), Digitoxin for LC assay, DIGITOXIN [INN], DIGITOXIN [JAN], DIGITOXIN [MI], DIGITOXIN [HSDB], DIGITOXIN [VANDF], DIGITOXINUM [HPUS], DIGITOXIN [WHO-DD], DIGITOXIN [WHO-IP], Digitoxin (JAN/USP/INN), SCHEMBL20940, CHEMBL254219, cid_441207, GTPL6782, MEGxp0_001901, DIGITOXIN [ORANGE BOOK], REGID_for_CID_441207, ACon0_000319, ACon1_000610, BDBM46356, HY-B1357R, C01AA04, 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.)-, HY-B1357, Tox21_111659, Tox21_302269, CP4071, LMST01120018, AKOS015915863, Digitoxin, >=92% (HPLC), powder, Tox21_111659_1, CCG-208538, CS-5502, DB01396, OD09336, SMP1_000096, USEPA/OPP Pesticide Code: 097002, NCGC00094652-06, NCGC00094652-07, NCGC00094652-09, NCGC00142623-02, NCGC00142623-03, NCGC00142623-04, NCGC00142623-05, NCGC00255265-01, 1ST11162, AS-75726, 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, (3beta,5beta)-3-((O-2,6-DIDEOXY-beta-D-RIBO-HEXAPYRANOSYL-(1->4)-2,6-DIDEOXY-beta-D-RIBO-HEXOPYRANOSYL)OXY)-14-HYDROXYCARD-20(22)-ENOLIDE, (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, (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, (3beta,5beta)-3-((O-2,6-Dideoxy-beta-D-ribohexopyranosyl-(1-4)-O-2,6-dideoxy-bet a-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14-hydro xycard-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, 200-760-5, 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-HEXOPYRANOSYL)OXY)-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-hexopyranosyloxy)-14-hydroxy-5beta,14beta-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-hydroxy-6-methyl(2H-3,4,5,6-tetrah ydropyran-2-yloxy), 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, 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, 5beta,20(22)-Cardenolide-3beta,14-diol-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, 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)-, CARD-20(22)-ENOLIDE, 3-((O-2,6-DIDEOXY-BETA-D-RIBO-HEXOPYRANOSYL-(HEXOPYRANOSYL-(1-4)-2,6-DIDEOXY-BETA-D-RIBO-HEXOPYRANOSYL)OXY)-14-HYDROXY-,(3BETA, 5BETA)-, Carditoxin, (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
Ghose Rule False
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 183.0
Hydrogen Bond Donor Count 5.0
Pfizer 3 75 Rule False
Scaffold Graph Level CC1CCC(C2CCC3C2CCC2C4CCC(CC5CCC(CC6CCC(CC7CCCCC7)CC6)CC5)CC4CCC23)C1
Np Classifier Class Cardenolides
Deep Smiles O=COCC=C5)[C@H]CC[C@][C@]5C)CC[C@H][C@H]6CC[C@H][C@]6C)CC[C@@H]C6)O[C@H]C[C@H]O)[C@@H][C@H]O6)C))O[C@H]C[C@H]O)[C@@H][C@H]O6)C))O[C@H]C[C@H]O)[C@@H][C@H]O6)C))O))))))))))))))))))))))))))))O
Heavy Atom Count 54.0
Classyfire Class Steroids and steroid derivatives
Description Digitoxin, also known as crystodigin or digitoxoside, belongs to cardenolide glycosides and derivatives class of compounds. Those are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. Thus, digitoxin is considered to be a sterol lipid molecule. Digitoxin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Digitoxin can be synthesized from digitoxigenin. Digitoxin can also be synthesized into 3'''-O-acetyldigitoxin. Digitoxin can be found in common bean, which makes digitoxin a potential biomarker for the consumption of this food product. Digitoxin can be found primarily in blood and urine. Digitoxin is a non-carcinogenic (not listed by IARC) potentially toxic compound. Digitoxin is a drug which is used for the treatment and management of congestive cardiac insufficiency, arrhythmias and heart failure. Digitoxin is a cardiac glycoside. 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, so could be used in patients with poor or erratic kidney function. However, it is now rarely used in current Western medical practice. 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 . Digitoxin exhibits similar toxic effects to the more-commonly used digoxin, namely: anorexia, nausea, vomiting, diarrhoea, confusion, visual disturbances, and cardiac arrhythmias (DrugBank). Digitoxin inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Digitoxin also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential (T3DB).
Scaffold Graph Node Level OC1CC(C2CCC3C2CCC2C4CCC(OC5CCC(OC6CCC(OC7CCCCO7)CO6)CO5)CC4CCC23)CO1
Classyfire Subclass Steroid lactones
Isotope Atom Count 0.0
Molecular Complexity 1410.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 20.0
Uniprot Id P05108, P08684, P05023, P08183, P46721, Q6ZQN7, P02768, P54710, P50997, n.a., P02545, P51151, P25779, P10636, P40763, P42224, O15118, P51450, P04637, Q16236, Q96QE3, P19793, P03372, P10275, P10828, Q96RI1, Q03181, P37231, P84022, P11473, P04150, P25094, P46720, O75496, O42275, P81908, Q9NUW8, O75874, Q9NPD5, Q9Y6L6, O95342, Q92887, O15438, O15439, P0DTD1, P19838, P05412
Iupac Name 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
Prediction Hob 1.0
Class Steroids and steroid derivatives
Veber Rule False
Classyfire Superclass Lipids and lipid-like molecules
Target Id NPT483, NPT537, NPT51, NPT38, NPT538, NPT539, NPT3812, NPT713
Xlogp 2.3
Superclass Lipids and lipid-like molecules
Subclass Steroid lactones
Gsk 4 400 Rule False
Molecular Formula C41H64O13
Scaffold Graph Node Bond Level O=C1C=C(C2CCC3C2CCC2C4CCC(OC5CCC(OC6CCC(OC7CCCCO7)CO6)CO5)CC4CCC23)CO1
Prediction Swissadme 0.0
Inchi Key WDJUZGPOPHTGOT-XUDUSOBPSA-N
Silicos It Class Soluble
Fcsp3 0.926829268292683
Logs -4.612
Rotatable Bond Count 7.0
State Solid
Logd 3.799
Synonyms Crystodigin, Digitoxoside, Digitoksin, Digitoxinum, Bürger, digitoxin, Didier, digitoxin, Digitoxin awd, Digitoxin didier, Digimed, Digophton, Nativelle, digitaline, Digimerck, Digitoxin bürger, AWD, digitoxin, Coramedan, Digitaline nativelle, Digitoxin philo, Digitoxin-philo, digitoxin, digitoxin,ban,inn,usan
Esol Class Moderately soluble
Functional Groups CC1=CC(=O)OC1, CO, C[C@H](OC)OC
Compound Name Digitoxin
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 764.435
Formal Charge 0.0
Monoisotopic Mass 764.435
Hydrogen Bond Acceptor Count 13.0
Molecular Weight 764.9
Gi Absorption False
Covalent Unit Count 1.0
Total Atom Stereocenter Count 20.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aliphatic heteropolycyclic compounds
Lipinski Rule Of 5 False
Esol -5.286190000000003
Inchi InChI=1S/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
Smiles C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2O)O[C@@H]3[C@H](O[C@H](C[C@@H]3O)O[C@H]4CC[C@]5([C@@H](C4)CC[C@@H]6[C@@H]5CC[C@]7([C@@]6(CC[C@@H]7C8=CC(=O)OC8)O)C)C)C)C)O)O
Nring 8.0
Np Classifier Biosynthetic Pathway Terpenoids
Defined Bond Stereocenter Count 0.0
Egan Rule False
Taxonomy Direct Parent Cardenolide glycosides and derivatives
Np Classifier Superclass Steroids

  • 1. Outgoing r'ship FOUND_IN to/from Aria Arguta (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 2. Outgoing r'ship FOUND_IN to/from Atropa Belladona (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 3. Outgoing r'ship FOUND_IN to/from Begonia Glabra (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 4. Outgoing r'ship FOUND_IN to/from Cordyline Fruticosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 5. Outgoing r'ship FOUND_IN to/from Digitalis Lanata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 6. Outgoing r'ship FOUND_IN to/from Digitalis Purpurea (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 7. Outgoing r'ship FOUND_IN to/from Erysimum Repandum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 8. Outgoing r'ship FOUND_IN to/from Hemerocallis Fulva (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 9. Outgoing r'ship FOUND_IN to/from Luffa Aegyptiaca (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 10. Outgoing r'ship FOUND_IN to/from Phaseolus Vulgaris (Plant) Rel Props:Source_db:fooddb_chem_all
  • 11. Outgoing r'ship FOUND_IN to/from Phoenix Canariensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 12. Outgoing r'ship FOUND_IN to/from Rubus Coreanus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 13. Outgoing r'ship FOUND_IN to/from Strychnos Splendens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all