digoxin   Click here for help

GtoPdb Ligand ID: 4726

Synonyms: Lanoxin®
Approved drug PDB Ligand
digoxin is an approved drug (FDA (no history prior to 1975))
Comment: Digoxin is a cardiac glycoside similar to digitoxin.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 6
Rotatable bonds 7
Topological polar surface area 203.06
Molecular weight 780.43
XLogP 2.17
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES O=C1OCC(=C1)C1CCC2(C1(C)C(O)CC1C2CCC2C1(C)CCC(C2)OC1CC(O)C(C(O1)C)OC1CC(O)C(C(O1)C)OC1CC(O)C(C(O1)C)O)O
Isomeric SMILES O=C1OCC(=C1)[C@H]1CC[C@]2([C@]1(C)[C@H](O)C[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@@H](C2)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O)O
InChI InChI=1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25-,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1
InChI Key LTMHDMANZUZIPE-PUGKRICDSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (no history prior to 1975))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-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}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one
International Nonproprietary Names Click here for help
INN number INN
389 digoxin
Synonyms Click here for help
Lanoxin®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9684074
Reactome Reaction Reactome logo R-HSA-9684068
Other databases
CAS Registry No. 20830-75-5 (source: Scifinder)
ChEBI CHEBI:4551
ChEMBL Ligand CHEMBL1751
DrugBank Ligand DB00390
DrugCentral Ligand 882
GtoPdb PubChem SID 178101437
PubChem CID 2724385
RCSB PDB Ligand DGX
Search Google for chemical match using the InChIKey LTMHDMANZUZIPE-PUGKRICDSA-N
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Search PubMed clinical trials digoxin
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Search UniChem for chemical match using the InChIKey LTMHDMANZUZIPE-PUGKRICDSA-N
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Wikipedia Digoxin

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Tocris
Digoxin
Cat. No. 4583