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3-[(2-Deoxyhexopyranosyl)oxy]-11,14-dihydroxy-12-oxo-7,8-epoxycard-20(22)-enolide

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 59773746-1aec-4725-a222-70617fee87b0
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
IUPAC Name (3R,5S,7S,10S,11S,12R,14R,15R)-7-[(2S,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-12,18-dihydroxy-10,14-dimethyl-15-(5-oxo-2H-furan-3-yl)-2-oxapentacyclo[9.7.0.01,3.05,10.014,18]octadecan-13-one
SMILES (Canonical) CC12CCC(CC1CC3C4(C2C(C(=O)C5(C4(CCC5C6=CC(=O)OC6)O)C)O)O3)OC7CC(C(C(O7)CO)O)O
SMILES (Isomeric) C[C@]12CC[C@@H](C[C@H]1C[C@@H]3C4([C@@H]2[C@H](C(=O)[C@]5(C4(CC[C@@H]5C6=CC(=O)OC6)O)C)O)O3)O[C@@H]7C[C@H]([C@@H]([C@H](O7)CO)O)O
InChI InChI=1S/C29H40O11/c1-26-5-3-15(38-21-10-17(31)22(33)18(11-30)39-21)8-14(26)9-19-29(40-19)24(26)23(34)25(35)27(2)16(4-6-28(27,29)36)13-7-20(32)37-12-13/h7,14-19,21-24,30-31,33-34,36H,3-6,8-12H2,1-2H3/t14-,15-,16+,17+,18+,19+,21-,22-,23+,24+,26-,27-,28?,29?/m0/s1
InChI Key NRBYBABUHKEQNM-WDVBEFSESA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H40O11
Molecular Weight 564.60 g/mol
Exact Mass 564.25706209 g/mol
Topological Polar Surface Area (TPSA) 176.00 Ų
XlogP -0.70
Atomic LogP (AlogP) -0.26
H-Bond Acceptor 11
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

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3-[(2-Deoxyhexopyranosyl)oxy]-11,14-dihydroxy-12-oxo-7,8-epoxycard-20(22)-enolide
(8xi)-3beta-[(2-Deoxy-alpha-D-arabino-hexopyranosyl)oxy]-11beta,14-dihydroxy-12-oxo-5beta,7alpha,14xi-7,8-epoxycard-20(22)-enolide

2D Structure

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2D Structure of 3-[(2-Deoxyhexopyranosyl)oxy]-11,14-dihydroxy-12-oxo-7,8-epoxycard-20(22)-enolide

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8000 80.00%
Caco-2 - 0.8594 85.94%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.7970 79.70%
OATP2B1 inhibitior - 0.5871 58.71%
OATP1B1 inhibitior + 0.8744 87.44%
OATP1B3 inhibitior + 0.9638 96.38%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.5721 57.21%
P-glycoprotein inhibitior + 0.5741 57.41%
P-glycoprotein substrate + 0.7375 73.75%
CYP3A4 substrate + 0.7134 71.34%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8917 89.17%
CYP3A4 inhibition - 0.7835 78.35%
CYP2C9 inhibition - 0.8072 80.72%
CYP2C19 inhibition - 0.8742 87.42%
CYP2D6 inhibition - 0.9228 92.28%
CYP1A2 inhibition - 0.8688 86.88%
CYP2C8 inhibition - 0.6624 66.24%
CYP inhibitory promiscuity - 0.9370 93.70%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6270 62.70%
Eye corrosion - 0.9874 98.74%
Eye irritation - 0.9311 93.11%
Skin irritation - 0.6156 61.56%
Skin corrosion - 0.9310 93.10%
Ames mutagenesis - 0.6817 68.17%
Human Ether-a-go-go-Related Gene inhibition + 0.7644 76.44%
Micronuclear - 0.6700 67.00%
Hepatotoxicity - 0.5741 57.41%
skin sensitisation - 0.8936 89.36%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity + 0.5492 54.92%
Acute Oral Toxicity (c) I 0.7780 77.80%
Estrogen receptor binding + 0.7539 75.39%
Androgen receptor binding + 0.7639 76.39%
Thyroid receptor binding - 0.6052 60.52%
Glucocorticoid receptor binding + 0.6604 66.04%
Aromatase binding + 0.7293 72.93%
PPAR gamma + 0.5595 55.95%
Honey bee toxicity - 0.7102 71.02%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.9685 96.85%

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 96.76% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.41% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.74% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 93.69% 100.00%
CHEMBL2581 P07339 Cathepsin D 93.57% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.96% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.74% 97.09%
CHEMBL226 P30542 Adenosine A1 receptor 92.24% 95.93%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.91% 94.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.49% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.25% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.93% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.82% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.56% 85.14%
CHEMBL3922 P50579 Methionine aminopeptidase 2 83.56% 97.28%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.12% 92.62%
CHEMBL5103 Q969S8 Histone deacetylase 10 81.21% 90.08%
CHEMBL1937 Q92769 Histone deacetylase 2 81.08% 94.75%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.97% 96.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 196656
LOTUS LTS0010106
wikiData Q82882434