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[(1S,3R,8S,9S,10R,13S,14S,17R)-17-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl] acetate

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 3feccd01-5e04-4520-9abf-09c928d5d0a4
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
IUPAC Name [(1S,3R,8S,9S,10R,13S,14S,17R)-17-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl] acetate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C36H54O11/c1-17-12-27(46-33(43)23(17)15-37)18(2)24-8-9-25-22-7-6-20-13-21(45-34-32(42)31(41)30(40)28(16-38)47-34)14-29(44-19(3)39)36(20,5)26(22)10-11-35(24,25)4/h6,18,21-22,24-32,34,37-38,40-42H,7-16H2,1-5H3/t18-,21+,22-,24+,25-,26-,27+,28+,29-,30+,31-,32+,34+,35+,36-/m0/s1
InChI Key SKADEWVNQSRPEJ-SQXNYGDCSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C36H54O11
Molecular Weight 662.80 g/mol
Exact Mass 662.36661253 g/mol
Topological Polar Surface Area (TPSA) 172.00 Ų
XlogP 3.70
Atomic LogP (AlogP) 2.55
H-Bond Acceptor 11
H-Bond Donor 5
Rotatable Bonds 7

Synonyms

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227179-08-0
Ergosta-5,24-dien-26-oic acid, 1-(acetyloxy)-3-(beta-D-glucopyranosyloxy)-22,27-dihydroxy-, delta-lactone, (1alpha,3beta,22R)-

2D Structure

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2D Structure of [(1S,3R,8S,9S,10R,13S,14S,17R)-17-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7135 71.35%
Caco-2 - 0.8723 87.23%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.8629 86.29%
OATP2B1 inhibitior - 0.8606 86.06%
OATP1B1 inhibitior + 0.8339 83.39%
OATP1B3 inhibitior + 0.7884 78.84%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.5298 52.98%
BSEP inhibitior - 0.4733 47.33%
P-glycoprotein inhibitior + 0.7298 72.98%
P-glycoprotein substrate + 0.5964 59.64%
CYP3A4 substrate + 0.7621 76.21%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9002 90.02%
CYP3A4 inhibition - 0.9295 92.95%
CYP2C9 inhibition - 0.9215 92.15%
CYP2C19 inhibition - 0.9385 93.85%
CYP2D6 inhibition - 0.9550 95.50%
CYP1A2 inhibition - 0.8971 89.71%
CYP2C8 inhibition + 0.6743 67.43%
CYP inhibitory promiscuity - 0.9438 94.38%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6009 60.09%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9289 92.89%
Skin irritation + 0.4910 49.10%
Skin corrosion - 0.9419 94.19%
Ames mutagenesis - 0.6770 67.70%
Human Ether-a-go-go-Related Gene inhibition + 0.6591 65.91%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.7158 71.58%
skin sensitisation - 0.9349 93.49%
Respiratory toxicity + 0.8667 86.67%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity + 0.4942 49.42%
Acute Oral Toxicity (c) III 0.5730 57.30%
Estrogen receptor binding + 0.7651 76.51%
Androgen receptor binding + 0.7386 73.86%
Thyroid receptor binding - 0.6525 65.25%
Glucocorticoid receptor binding + 0.6557 65.57%
Aromatase binding + 0.6272 62.72%
PPAR gamma + 0.6282 62.82%
Honey bee toxicity - 0.6486 64.86%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9668 96.68%

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 97.12% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.08% 96.09%
CHEMBL2581 P07339 Cathepsin D 94.78% 98.95%
CHEMBL5103 Q969S8 Histone deacetylase 10 93.94% 90.08%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.24% 97.09%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 92.49% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.72% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.52% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.46% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.91% 100.00%
CHEMBL1937 Q92769 Histone deacetylase 2 90.73% 94.75%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 90.39% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.87% 86.33%
CHEMBL253 P34972 Cannabinoid CB2 receptor 88.29% 97.25%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.26% 94.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 86.57% 93.56%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 86.54% 93.04%
CHEMBL5028 O14672 ADAM10 86.41% 97.50%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.31% 99.23%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.63% 97.14%
CHEMBL237 P41145 Kappa opioid receptor 83.29% 98.10%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.93% 99.17%
CHEMBL5255 O00206 Toll-like receptor 4 82.91% 92.50%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 80.85% 98.75%
CHEMBL226 P30542 Adenosine A1 receptor 80.01% 95.93%

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.
Physalis peruviana

Cross-Links

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PubChem 10675875
LOTUS LTS0183394
wikiData Q105254687