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3-[(3S,5R,8R,9S,10S,13R,14S,16S,17S)-14,16-dihydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

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 5a1be448-8e61-4cbb-afea-726a6dcf3e0b
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,13R,14S,16S,17S)-14,16-dihydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-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(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CC(C5C6=CC(=O)OC6)O)O)C)C)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(C[C@@H]([C@H]5C6=CC(=O)OC6)O)O)C)C)O)O)O
InChI InChI=1S/C29H44O9/c1-14-23(32)24(33)25(34)26(37-14)38-17-6-8-27(2)16(11-17)4-5-19-18(27)7-9-28(3)22(15-10-21(31)36-13-15)20(30)12-29(19,28)35/h10,14,16-20,22-26,30,32-35H,4-9,11-13H2,1-3H3/t14-,16+,17-,18-,19+,20-,22+,23-,24+,25+,26-,27-,28+,29-/m0/s1
InChI Key NPOLNOGRUIDOKL-MOUYIVCRSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H44O9
Molecular Weight 536.70 g/mol
Exact Mass 536.29853298 g/mol
Topological Polar Surface Area (TPSA) 146.00 Ų
XlogP 0.80
Atomic LogP (AlogP) 1.43
H-Bond Acceptor 9
H-Bond Donor 5
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 3-[(3S,5R,8R,9S,10S,13R,14S,16S,17S)-14,16-dihydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9219 92.19%
Caco-2 - 0.8473 84.73%
Blood Brain Barrier - 0.9000 90.00%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.8297 82.97%
OATP2B1 inhibitior - 0.6046 60.46%
OATP1B1 inhibitior + 0.9363 93.63%
OATP1B3 inhibitior + 0.9518 95.18%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior - 0.4819 48.19%
P-glycoprotein inhibitior - 0.5193 51.93%
P-glycoprotein substrate + 0.6747 67.47%
CYP3A4 substrate + 0.7168 71.68%
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 - 0.7078 70.78%
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 - 0.9402 94.02%
Skin irritation + 0.5359 53.59%
Skin corrosion - 0.9388 93.88%
Ames mutagenesis - 0.6293 62.93%
Human Ether-a-go-go-Related Gene inhibition + 0.7938 79.38%
Micronuclear - 0.8300 83.00%
Hepatotoxicity - 0.7067 70.67%
skin sensitisation - 0.9042 90.42%
Respiratory toxicity + 0.9000 90.00%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity - 0.7594 75.94%
Acute Oral Toxicity (c) I 0.7867 78.67%
Estrogen receptor binding + 0.7398 73.98%
Androgen receptor binding + 0.8000 80.00%
Thyroid receptor binding - 0.6062 60.62%
Glucocorticoid receptor binding + 0.6632 66.32%
Aromatase binding + 0.7118 71.18%
PPAR gamma - 0.4836 48.36%
Honey bee toxicity - 0.6830 68.30%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity + 0.6200 62.00%
Fish aquatic toxicity + 0.9750 97.50%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.26% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.76% 96.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 95.31% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.26% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.83% 86.33%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.50% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.76% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.86% 95.89%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.51% 85.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.73% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.41% 95.56%
CHEMBL3714130 P46095 G-protein coupled receptor 6 86.55% 97.36%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 85.90% 82.69%
CHEMBL1871 P10275 Androgen Receptor 85.17% 96.43%
CHEMBL2581 P07339 Cathepsin D 85.10% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.09% 94.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 84.41% 96.77%
CHEMBL241 Q14432 Phosphodiesterase 3A 83.66% 92.94%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.57% 99.23%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 82.01% 93.04%

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.
Dipcadi glaucum

Cross-Links

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PubChem 163003402
LOTUS LTS0198734
wikiData Q105183250