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(2R)-2-[(1S)-1-[(5R,6R,8R,9S,10R,13S,14R,17S)-5-ethoxy-6,14,17-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-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 96566332-bafd-4adb-8b50-06fc75dfb99e
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1S)-1-[(5R,6R,8R,9S,10R,13S,14R,17S)-5-ethoxy-6,14,17-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
SMILES (Canonical) CCOC12CC=CC(=O)C1(C3CCC4(C(C3CC2O)(CCC4(C(C)(C5CC(=C(C(=O)O5)C)C)O)O)O)C)C
SMILES (Isomeric) CCO[C@]12CC=CC(=O)[C@@]1([C@H]3CC[C@]4([C@]([C@@H]3C[C@H]2O)(CC[C@]4([C@](C)([C@H]5CC(=C(C(=O)O5)C)C)O)O)O)C)C
InChI InChI=1S/C30H44O8/c1-7-37-29-11-8-9-21(31)26(29,5)19-10-12-25(4)28(35,20(19)16-22(29)32)13-14-30(25,36)27(6,34)23-15-17(2)18(3)24(33)38-23/h8-9,19-20,22-23,32,34-36H,7,10-16H2,1-6H3/t19-,20+,22+,23+,25-,26-,27-,28+,29-,30-/m0/s1
InChI Key OABXIBGLROZKOQ-YBQQWVNGSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C30H44O8
Molecular Weight 532.70 g/mol
Exact Mass 532.30361836 g/mol
Topological Polar Surface Area (TPSA) 134.00 Ų
XlogP 1.70
Atomic LogP (AlogP) 2.75
H-Bond Acceptor 8
H-Bond Donor 4
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-2-[(1S)-1-[(5R,6R,8R,9S,10R,13S,14R,17S)-5-ethoxy-6,14,17-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-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 + 0.9090 90.90%
Caco-2 - 0.7129 71.29%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.7934 79.34%
OATP2B1 inhibitior - 0.8608 86.08%
OATP1B1 inhibitior + 0.8514 85.14%
OATP1B3 inhibitior + 0.9418 94.18%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7068 70.68%
BSEP inhibitior + 0.9068 90.68%
P-glycoprotein inhibitior + 0.6283 62.83%
P-glycoprotein substrate + 0.6463 64.63%
CYP3A4 substrate + 0.7296 72.96%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9044 90.44%
CYP3A4 inhibition - 0.7472 74.72%
CYP2C9 inhibition - 0.8607 86.07%
CYP2C19 inhibition - 0.8773 87.73%
CYP2D6 inhibition - 0.9386 93.86%
CYP1A2 inhibition - 0.8806 88.06%
CYP2C8 inhibition + 0.6183 61.83%
CYP inhibitory promiscuity - 0.8969 89.69%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7053 70.53%
Eye corrosion - 0.9924 99.24%
Eye irritation - 0.9283 92.83%
Skin irritation + 0.6291 62.91%
Skin corrosion - 0.9420 94.20%
Ames mutagenesis - 0.6661 66.61%
Human Ether-a-go-go-Related Gene inhibition + 0.8086 80.86%
Micronuclear - 0.7800 78.00%
Hepatotoxicity + 0.5857 58.57%
skin sensitisation - 0.9229 92.29%
Respiratory toxicity + 0.8333 83.33%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity + 0.7288 72.88%
Acute Oral Toxicity (c) III 0.4100 41.00%
Estrogen receptor binding + 0.7932 79.32%
Androgen receptor binding + 0.7756 77.56%
Thyroid receptor binding + 0.5580 55.80%
Glucocorticoid receptor binding + 0.7399 73.99%
Aromatase binding + 0.7951 79.51%
PPAR gamma + 0.6368 63.68%
Honey bee toxicity - 0.7812 78.12%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6600 66.00%
Fish aquatic toxicity + 0.9859 98.59%

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
CHEMBL4040 P28482 MAP kinase ERK2 99.70% 83.82%
CHEMBL253 P34972 Cannabinoid CB2 receptor 99.21% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.00% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.64% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.41% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.46% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.14% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.73% 86.33%
CHEMBL1871 P10275 Androgen Receptor 91.06% 96.43%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 90.68% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.00% 100.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 88.25% 93.56%
CHEMBL2996 Q05655 Protein kinase C delta 87.71% 97.79%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.70% 99.23%
CHEMBL2581 P07339 Cathepsin D 87.31% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.72% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.65% 95.89%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 85.18% 90.93%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.16% 100.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.83% 94.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.64% 92.62%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.15% 93.04%
CHEMBL1907 P15144 Aminopeptidase N 80.55% 93.31%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.36% 94.45%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 80.01% 97.33%

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.
Withania somnifera

Cross-Links

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PubChem 163030449
LOTUS LTS0195214
wikiData Q105188596