Digoxin
| Internal ID | 2558f4d8-56ca-43d1-9e68-4eadc0587099 |
| Taxonomy | Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives |
| IUPAC Name | 3-[(3S,5R,8R,9S,10S,12R,13S,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-12,14-dihydroxy-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 |
| SMILES (Canonical) | CC1C(C(CC(O1)OC2C(OC(CC2O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5CC(C7(C6(CCC7C8=CC(=O)OC8)O)C)O)C)C)C)O)O |
| SMILES (Isomeric) | 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]5C[C@H]([C@]7([C@@]6(CC[C@@H]7C8=CC(=O)OC8)O)C)O)C)C)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 |
| Popularity | 30,596 references in papers |
| Molecular Formula | C41H64O14 |
| Molecular Weight | 780.90 g/mol |
| Exact Mass | 780.42960671 g/mol |
| Topological Polar Surface Area (TPSA) | 203.00 Ų |
| XlogP | 1.30 |
| Atomic LogP (AlogP) | 2.22 |
| H-Bond Acceptor | 14 |
| H-Bond Donor | 6 |
| Rotatable Bonds | 7 |
| 20830-75-5 |
| Lanoxin |
| 12beta-Hydroxydigitoxin |
| Dilanacin |
| Rougoxin |
| Digacin |
| Lanoxicaps |
| Dynamos |
| Mapluxin |
| Vanoxin |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9219 | 92.19% |
| Caco-2 | - | 0.9372 | 93.72% |
| Blood Brain Barrier | - | 0.9000 | 90.00% |
| Human oral bioavailability | + | 0.7143 | 71.43% |
| Subcellular localzation | Mitochondria | 0.8297 | 82.97% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.9462 | 94.62% |
| OATP1B3 inhibitior | + | 0.9518 | 95.18% |
| MATE1 inhibitior | - | 1.0000 | 100.00% |
| OCT2 inhibitior | - | 0.9750 | 97.50% |
| BSEP inhibitior | + | 0.9072 | 90.72% |
| P-glycoprotein inhibitior | + | 0.7311 | 73.11% |
| P-glycoprotein substrate | + | 0.9444 | 94.44% |
| CYP3A4 substrate | + | 0.5907 | 59.07% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.9026 | 90.26% |
| CYP3A4 inhibition | - | 0.9279 | 92.79% |
| CYP2C9 inhibition | - | 0.9196 | 91.96% |
| CYP2C19 inhibition | - | 0.9385 | 93.85% |
| CYP2D6 inhibition | - | 0.9359 | 93.59% |
| CYP1A2 inhibition | - | 0.9261 | 92.61% |
| CYP2C8 inhibition | - | 0.9882 | 98.82% |
| CYP inhibitory promiscuity | - | 0.9279 | 92.79% |
| UGT catelyzed | + | 0.8000 | 80.00% |
| Carcinogenicity (binary) | - | 1.0000 | 100.00% |
| Carcinogenicity (trinary) | Non-required | 0.5632 | 56.32% |
| Eye corrosion | - | 0.9902 | 99.02% |
| Eye irritation | - | 0.9541 | 95.41% |
| Skin irritation | + | 0.5359 | 53.59% |
| Skin corrosion | - | 0.9388 | 93.88% |
| Ames mutagenesis | - | 0.5079 | 50.79% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.8916 | 89.16% |
| Micronuclear | - | 0.8300 | 83.00% |
| Hepatotoxicity | - | 0.8375 | 83.75% |
| skin sensitisation | - | 0.9042 | 90.42% |
| Respiratory toxicity | + | 0.8333 | 83.33% |
| Reproductive toxicity | + | 0.9000 | 90.00% |
| Mitochondrial toxicity | + | 0.6625 | 66.25% |
| Nephrotoxicity | - | 0.8450 | 84.50% |
| Acute Oral Toxicity (c) | I | 0.7867 | 78.67% |
| Estrogen receptor binding | + | 0.8906 | 89.06% |
| Androgen receptor binding | + | 0.8696 | 86.96% |
| Thyroid receptor binding | - | 0.7924 | 79.24% |
| Glucocorticoid receptor binding | + | 0.6919 | 69.19% |
| Aromatase binding | + | 0.8314 | 83.14% |
| PPAR gamma | + | 0.7635 | 76.35% |
| Honey bee toxicity | - | 0.7206 | 72.06% |
| Biodegradation | - | 0.6750 | 67.50% |
| Crustacea aquatic toxicity | + | 0.6100 | 61.00% |
| Fish aquatic toxicity | + | 0.9750 | 97.50% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL2524 | P06280 | Alpha-galactosidase A |
31622.8 nM |
Potency |
via CMAUP
|
| CHEMBL1293236 | P46063 | ATP-dependent DNA helicase Q1 |
3981.1 nM |
Potency |
via CMAUP
|
| CHEMBL4096 | P04637 | Cellular tumor antigen p53 |
158.5 nM 158.5 nM 199.5 nM 79.4 nM |
Potency Potency Potency Potency |
via Super-PRED
via CMAUP via CMAUP via Super-PRED |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha |
125.9 nM |
Potency |
via Super-PRED
|
| CHEMBL1293277 | O15118 | Niemann-Pick C1 protein |
223.9 nM 223.9 nM 223.9 nM |
Potency Potency Potency |
via Super-PRED
via CMAUP via CMAUP |
| CHEMBL1741186 | P51449 | Nuclear receptor ROR-gamma |
1980 nM 2000 nM 4000 nM 4100 nM |
IC50 IC50 IC50 IC50 |
PMID: 24502334
PMID: 24040486 DOI: 10.1039/C3MD00005B PMID: 24502334 |
| CHEMBL2362980 | Q06710 | Paired box protein Pax-8 |
414 nM |
AC50 |
via CMAUP
|
| CHEMBL1293235 | P02545 | Prelamin-A/C |
20 nM 4466.8 nM 562.3 nM 562.3 nM |
Potency Potency Potency Potency |
via Super-PRED
via CMAUP via CMAUP via Super-PRED |
| CHEMBL1293294 | P51151 | Ras-related protein Rab-9A |
281.8 nM 223.9 nM 223.9 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via Super-PRED |
| CHEMBL4026 | P40763 | Signal transducer and activator of transcription 3 |
1862 nM |
IC50 |
via CMAUP
|
| CHEMBL1807 | P05023 | Sodium/potassium-transporting ATPase alpha-1 chain |
290 nM 290 nM |
IC50 IC50 |
PMID: 26122772
via Super-PRED |
| CHEMBL1697668 | Q9Y6L6 | Solute carrier organic anion transporter family member 1B1 |
3235.94 nM |
IC50 |
PMID: 23571415
|
| CHEMBL1743121 | Q9NPD5 | Solute carrier organic anion transporter family member 1B3 |
13182.57 nM |
IC50 |
PMID: 23571415
|
| CHEMBL1293232 | Q16637 | Survival motor neuron protein |
794.3 nM |
Potency |
via Super-PRED
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 97.73% | 91.11% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 95.93% | 100.00% |
| CHEMBL4026 | P40763 | Signal transducer and activator of transcription 3 | 95.14% | 82.69% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 94.26% | 96.09% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 94.17% | 97.09% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 92.85% | 94.45% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 90.81% | 95.56% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 89.46% | 86.33% |
| CHEMBL4303 | P08238 | Heat shock protein HSP 90-beta | 88.76% | 96.77% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 86.40% | 95.89% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 86.25% | 89.00% |
| CHEMBL1871 | P10275 | Androgen Receptor | 85.95% | 96.43% |
| CHEMBL241 | Q14432 | Phosphodiesterase 3A | 84.57% | 92.94% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 84.36% | 99.23% |
| CHEMBL4040 | P28482 | MAP kinase ERK2 | 83.15% | 83.82% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 80.81% | 94.00% |
| CHEMBL3713062 | P10646 | Tissue factor pathway inhibitor | 80.18% | 97.33% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
To see more specific details click the taxa you are interested in.
To see more specific details click the taxa you are interested in.
| PubChem | 2724385 |
| NPASS | NPC173555 |
| ChEMBL | CHEMBL1751 |
| LOTUS | LTS0162755 |
| wikiData | Q422222 |