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Digitogenin

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 14488ed6-c29b-447b-a3df-a5e4c5977170
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (1R,2S,3S,4R,5'R,6R,7S,8R,9S,12S,13S,15R,16R,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-3,15,16-triol
SMILES (Canonical) CC1CCC2(C(C3C(O2)C(C4C3(CCC5C4CCC6C5(CC(C(C6)O)O)C)C)O)C)OC1
SMILES (Isomeric) C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)[C@H]([C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(C[C@H]([C@@H](C6)O)O)C)C)O)C)OC1
InChI InChI=1S/C27H44O5/c1-14-7-10-27(31-13-14)15(2)21-24(32-27)23(30)22-17-6-5-16-11-19(28)20(29)12-26(16,4)18(17)8-9-25(21,22)3/h14-24,28-30H,5-13H2,1-4H3/t14-,15+,16+,17-,18+,19-,20-,21+,22-,23+,24-,25-,26+,27-/m1/s1
InChI Key COVOPPXLDJVUSC-JPYPKGSXSA-N
Popularity 65 references in papers

Physical and Chemical Properties

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Molecular Formula C27H44O5
Molecular Weight 448.60 g/mol
Exact Mass 448.31887450 g/mol
Topological Polar Surface Area (TPSA) 79.20 Ų
XlogP 4.50
Atomic LogP (AlogP) 3.74
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 0

Synonyms

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Digitonin aglycon
Digitogenin [MI]
511-34-2
UNII-0KY44Q8S8O
0KY44Q8S8O
(25R)-5alpha-spirostan-2alpha,3beta,15beta-triol
Spirostan-2,3,15-triol, (2alpha,3beta,5alpha,15beta,25R)-
(1R,2S,3S,4R,5'R,6R,7S,8R,9S,12S,13S,15R,16R,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-3,15,16-triol
C08896
SCHEMBL1746877
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Digitogenin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8725 87.25%
Caco-2 - 0.6796 67.96%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.7301 73.01%
OATP2B1 inhibitior - 0.5757 57.57%
OATP1B1 inhibitior + 0.9006 90.06%
OATP1B3 inhibitior + 0.8524 85.24%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior - 0.8218 82.18%
P-glycoprotein inhibitior - 0.6700 67.00%
P-glycoprotein substrate - 0.6095 60.95%
CYP3A4 substrate + 0.7269 72.69%
CYP2C9 substrate - 0.7896 78.96%
CYP2D6 substrate - 0.7545 75.45%
CYP3A4 inhibition - 0.9296 92.96%
CYP2C9 inhibition - 0.9423 94.23%
CYP2C19 inhibition - 0.9237 92.37%
CYP2D6 inhibition - 0.9562 95.62%
CYP1A2 inhibition - 0.8689 86.89%
CYP2C8 inhibition - 0.6007 60.07%
CYP inhibitory promiscuity - 0.9801 98.01%
UGT catelyzed + 1.0000 100.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5834 58.34%
Eye corrosion - 0.9908 99.08%
Eye irritation - 0.9246 92.46%
Skin irritation - 0.5825 58.25%
Skin corrosion - 0.9324 93.24%
Ames mutagenesis - 0.7900 79.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4360 43.60%
Micronuclear - 0.9200 92.00%
Hepatotoxicity - 0.7875 78.75%
skin sensitisation - 0.9146 91.46%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity - 0.7374 73.74%
Acute Oral Toxicity (c) III 0.4324 43.24%
Estrogen receptor binding + 0.6480 64.80%
Androgen receptor binding + 0.6749 67.49%
Thyroid receptor binding + 0.5421 54.21%
Glucocorticoid receptor binding + 0.7214 72.14%
Aromatase binding + 0.7317 73.17%
PPAR gamma - 0.5199 51.99%
Honey bee toxicity - 0.5141 51.41%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.5600 56.00%
Fish aquatic toxicity + 0.8853 88.53%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.68% 96.09%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 95.51% 89.05%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.56% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.41% 91.11%
CHEMBL1994 P08235 Mineralocorticoid receptor 93.38% 100.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.97% 97.25%
CHEMBL204 P00734 Thrombin 90.77% 96.01%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 90.59% 96.38%
CHEMBL237 P41145 Kappa opioid receptor 88.25% 98.10%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 88.21% 82.69%
CHEMBL1163125 O60885 Bromodomain-containing protein 4 87.78% 97.31%
CHEMBL5600 P27448 Serine/threonine-protein kinase c-TAK1 87.18% 88.81%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 86.77% 96.77%
CHEMBL218 P21554 Cannabinoid CB1 receptor 85.67% 96.61%
CHEMBL221 P23219 Cyclooxygenase-1 85.48% 90.17%
CHEMBL259 P32245 Melanocortin receptor 4 85.34% 95.38%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 85.32% 95.58%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.93% 95.89%
CHEMBL301 P24941 Cyclin-dependent kinase 2 83.24% 91.23%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.39% 93.56%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.97% 93.04%
CHEMBL1871 P10275 Androgen Receptor 81.89% 96.43%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.75% 89.00%
CHEMBL3922 P50579 Methionine aminopeptidase 2 80.78% 97.28%
CHEMBL3137261 O14744 PRMT5/MEP50 complex 80.68% 100.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.64% 100.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 80.56% 95.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.27% 95.89%
CHEMBL340 P08684 Cytochrome P450 3A4 80.14% 91.19%
CHEMBL2431 P31751 Serine/threonine-protein kinase AKT2 80.06% 98.33%

Plants that contains it

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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.
Digitalis lanata

Cross-Links

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PubChem 441886
NPASS NPC19135
LOTUS LTS0007280
wikiData Q5643134