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(2R)-2-[(1S)-1-hydroxy-1-[(4S,5S,6R,8R,9S,10R,13S,14R,15S,17S)-4,5,6,14,17-pentahydroxy-15-methoxy-10,13-dimethyl-1-oxo-3,4,6,7,8,9,11,12,15,16-decahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-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 5191c20a-08ea-4447-9b70-92dfd86bde47
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1S)-1-hydroxy-1-[(4S,5S,6R,8R,9S,10R,13S,14R,15S,17S)-4,5,6,14,17-pentahydroxy-15-methoxy-10,13-dimethyl-1-oxo-3,4,6,7,8,9,11,12,15,16-decahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C29H44O10/c1-14-11-21(39-23(33)15(14)2)26(5,34)27(35)13-22(38-6)28(36)17-12-20(32)29(37)19(31)8-7-18(30)25(29,4)16(17)9-10-24(27,28)3/h16-17,19-22,31-32,34-37H,7-13H2,1-6H3/t16-,17+,19-,20+,21+,22-,24+,25-,26-,27-,28-,29-/m0/s1
InChI Key GLIWPQHNZJTEGA-PROOTGEZSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C29H44O10
Molecular Weight 552.70 g/mol
Exact Mass 552.29344760 g/mol
Topological Polar Surface Area (TPSA) 174.00 Ų
XlogP -0.80
Atomic LogP (AlogP) 0.53
H-Bond Acceptor 10
H-Bond Donor 6
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-2-[(1S)-1-hydroxy-1-[(4S,5S,6R,8R,9S,10R,13S,14R,15S,17S)-4,5,6,14,17-pentahydroxy-15-methoxy-10,13-dimethyl-1-oxo-3,4,6,7,8,9,11,12,15,16-decahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8720 87.20%
Caco-2 - 0.7592 75.92%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.6863 68.63%
OATP2B1 inhibitior - 0.5739 57.39%
OATP1B1 inhibitior + 0.8961 89.61%
OATP1B3 inhibitior + 0.9192 91.92%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7124 71.24%
BSEP inhibitior - 0.4801 48.01%
P-glycoprotein inhibitior - 0.4403 44.03%
P-glycoprotein substrate - 0.5143 51.43%
CYP3A4 substrate + 0.7383 73.83%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9032 90.32%
CYP3A4 inhibition - 0.8418 84.18%
CYP2C9 inhibition - 0.8793 87.93%
CYP2C19 inhibition - 0.8575 85.75%
CYP2D6 inhibition - 0.9439 94.39%
CYP1A2 inhibition - 0.7799 77.99%
CYP2C8 inhibition + 0.5674 56.74%
CYP inhibitory promiscuity - 0.9700 97.00%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6580 65.80%
Eye corrosion - 0.9916 99.16%
Eye irritation - 0.9248 92.48%
Skin irritation + 0.5351 53.51%
Skin corrosion - 0.9239 92.39%
Ames mutagenesis - 0.7516 75.16%
Human Ether-a-go-go-Related Gene inhibition - 0.4000 40.00%
Micronuclear - 0.7300 73.00%
Hepatotoxicity + 0.6232 62.32%
skin sensitisation - 0.8644 86.44%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity + 0.6920 69.20%
Acute Oral Toxicity (c) I 0.4363 43.63%
Estrogen receptor binding + 0.7264 72.64%
Androgen receptor binding + 0.7728 77.28%
Thyroid receptor binding + 0.5156 51.56%
Glucocorticoid receptor binding + 0.6880 68.80%
Aromatase binding + 0.7756 77.56%
PPAR gamma + 0.6133 61.33%
Honey bee toxicity - 0.8114 81.14%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity + 0.9622 96.22%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 99.38% 85.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.60% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.52% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 92.99% 99.23%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.46% 97.09%
CHEMBL241 Q14432 Phosphodiesterase 3A 91.30% 92.94%
CHEMBL1871 P10275 Androgen Receptor 90.01% 96.43%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 89.51% 97.14%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 88.85% 93.04%
CHEMBL1937 Q92769 Histone deacetylase 2 88.46% 94.75%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.37% 100.00%
CHEMBL204 P00734 Thrombin 88.01% 96.01%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 86.57% 91.11%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.47% 94.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 85.39% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.34% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.12% 95.89%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.67% 91.07%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 82.70% 93.03%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 82.54% 82.69%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.47% 92.62%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 82.37% 97.33%
CHEMBL259 P32245 Melanocortin receptor 4 81.54% 95.38%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 80.81% 82.38%
CHEMBL2959 Q08881 Tyrosine-protein kinase ITK/TSK 80.38% 95.00%

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 angulata

Cross-Links

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PubChem 102471219
LOTUS LTS0188676
wikiData Q105010958