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3-[(3S,5R,8R,9S,10R,13R,14S,17S)-14-hydroxy-3-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-dimethoxyoxan-2-yl]oxy-10-(hydroxymethyl)-13-methyl-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 c418b04d-bc84-4a27-9e6a-e15e6268bc84
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,10R,13R,14S,17S)-14-hydroxy-3-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-dimethoxyoxan-2-yl]oxy-10-(hydroxymethyl)-13-methyl-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) CC12CCC3C(C1(CCC2C4=CC(=O)OC4)O)CCC5C3(CCC(C5)OC6C(C(C(C(O6)CO)O)OC)OC)CO
SMILES (Isomeric) C[C@]12CC[C@H]3[C@H]([C@]1(CC[C@H]2C4=CC(=O)OC4)O)CC[C@H]5[C@@]3(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)OC)OC)CO
InChI InChI=1S/C31H48O10/c1-29-9-7-21-22(31(29,36)11-8-20(29)17-12-24(34)39-15-17)5-4-18-13-19(6-10-30(18,21)16-33)40-28-27(38-3)26(37-2)25(35)23(14-32)41-28/h12,18-23,25-28,32-33,35-36H,4-11,13-16H2,1-3H3/t18-,19+,20+,21+,22-,23-,25-,26+,27-,28-,29-,30-,31+/m1/s1
InChI Key NKNNPDNZCQCSJE-XRYJRNQQSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C31H48O10
Molecular Weight 580.70 g/mol
Exact Mass 580.32474772 g/mol
Topological Polar Surface Area (TPSA) 144.00 Ų
XlogP 0.90
Atomic LogP (AlogP) 1.71
H-Bond Acceptor 10
H-Bond Donor 4
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 3-[(3S,5R,8R,9S,10R,13R,14S,17S)-14-hydroxy-3-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-dimethoxyoxan-2-yl]oxy-10-(hydroxymethyl)-13-methyl-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 + 0.9031 90.31%
Caco-2 - 0.8346 83.46%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.7765 77.65%
OATP2B1 inhibitior - 0.5945 59.45%
OATP1B1 inhibitior + 0.9076 90.76%
OATP1B3 inhibitior + 0.9519 95.19%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.5271 52.71%
P-glycoprotein inhibitior + 0.5976 59.76%
P-glycoprotein substrate + 0.6532 65.32%
CYP3A4 substrate + 0.7173 71.73%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9020 90.20%
CYP3A4 inhibition - 0.8983 89.83%
CYP2C9 inhibition - 0.9110 91.10%
CYP2C19 inhibition - 0.9207 92.07%
CYP2D6 inhibition - 0.9432 94.32%
CYP1A2 inhibition - 0.9286 92.86%
CYP2C8 inhibition - 0.5635 56.35%
CYP inhibitory promiscuity - 0.8822 88.22%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5625 56.25%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9427 94.27%
Skin irritation - 0.5713 57.13%
Skin corrosion - 0.9454 94.54%
Ames mutagenesis - 0.6770 67.70%
Human Ether-a-go-go-Related Gene inhibition + 0.7777 77.77%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.6750 67.50%
skin sensitisation - 0.9215 92.15%
Respiratory toxicity + 0.9000 90.00%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity - 0.7158 71.58%
Acute Oral Toxicity (c) I 0.8135 81.35%
Estrogen receptor binding + 0.7783 77.83%
Androgen receptor binding + 0.8281 82.81%
Thyroid receptor binding - 0.6076 60.76%
Glucocorticoid receptor binding + 0.6465 64.65%
Aromatase binding + 0.6513 65.13%
PPAR gamma + 0.5383 53.83%
Honey bee toxicity - 0.6442 64.42%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.8932 89.32%

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 98.65% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.49% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 98.24% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 95.85% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.80% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.78% 97.25%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 92.54% 96.77%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 88.97% 82.69%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.83% 85.14%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 88.26% 94.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.17% 86.33%
CHEMBL5255 O00206 Toll-like receptor 4 87.62% 92.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.28% 95.89%
CHEMBL2581 P07339 Cathepsin D 87.16% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.87% 95.56%
CHEMBL241 Q14432 Phosphodiesterase 3A 85.20% 92.94%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.35% 92.62%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 81.94% 96.21%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.24% 97.14%

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.
Streblus asper

Cross-Links

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PubChem 163034092
LOTUS LTS0116325
wikiData Q105180667