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(2R)-2-[(1S)-1-[(5R,6R,8R,9S,10R,13S,14R,17S)-6-ethoxy-5,14,17-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 2d367133-c57c-4753-85c6-2d7490091612
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)-6-ethoxy-5,14,17-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) CCOC1CC2C(CCC3(C2(CCC3(C(C)(C4CC(=C(C(=O)O4)C)C)O)O)O)C)C5(C1(CC=CC5=O)O)C
SMILES (Isomeric) CCO[C@@H]1C[C@@H]2[C@H](CC[C@]3([C@]2(CC[C@]3([C@](C)([C@H]4CC(=C(C(=O)O4)C)C)O)O)O)C)[C@@]5([C@@]1(CC=CC5=O)O)C
InChI InChI=1S/C30H44O8/c1-7-37-23-16-20-19(26(5)21(31)9-8-11-29(23,26)35)10-12-25(4)28(20,34)13-14-30(25,36)27(6,33)22-15-17(2)18(3)24(32)38-22/h8-9,19-20,22-23,33-36H,7,10-16H2,1-6H3/t19-,20+,22+,23+,25-,26-,27-,28+,29-,30-/m0/s1
InChI Key JEYATKFYIGLJIM-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)-6-ethoxy-5,14,17-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 - 0.7082 70.82%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.7934 79.34%
OATP2B1 inhibitior - 0.8621 86.21%
OATP1B1 inhibitior + 0.8917 89.17%
OATP1B3 inhibitior + 0.9418 94.18%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7068 70.68%
BSEP inhibitior + 0.9063 90.63%
P-glycoprotein inhibitior + 0.6333 63.33%
P-glycoprotein substrate + 0.5585 55.85%
CYP3A4 substrate + 0.7174 71.74%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9079 90.79%
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 + 0.6348 63.48%
CYP inhibitory promiscuity - 0.8969 89.69%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7053 70.53%
Eye corrosion - 0.9924 99.24%
Eye irritation - 0.9294 92.94%
Skin irritation + 0.6291 62.91%
Skin corrosion - 0.9420 94.20%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7910 79.10%
Micronuclear - 0.7800 78.00%
Hepatotoxicity + 0.5787 57.87%
skin sensitisation - 0.9229 92.29%
Respiratory toxicity + 0.7667 76.67%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity + 0.8009 80.09%
Acute Oral Toxicity (c) III 0.4100 41.00%
Estrogen receptor binding + 0.7777 77.77%
Androgen receptor binding + 0.7690 76.90%
Thyroid receptor binding + 0.5887 58.87%
Glucocorticoid receptor binding + 0.7357 73.57%
Aromatase binding + 0.7847 78.47%
PPAR gamma + 0.6174 61.74%
Honey bee toxicity - 0.8046 80.46%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.7000 70.00%
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
CHEMBL253 P34972 Cannabinoid CB2 receptor 99.68% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.33% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.52% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.01% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.85% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.64% 86.33%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 90.93% 97.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 89.86% 96.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.68% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 88.25% 93.04%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.95% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.89% 89.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 86.32% 93.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.04% 95.89%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.33% 92.62%
CHEMBL2996 Q05655 Protein kinase C delta 83.98% 97.79%
CHEMBL1871 P10275 Androgen Receptor 83.83% 96.43%
CHEMBL2581 P07339 Cathepsin D 82.56% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.53% 94.00%
CHEMBL4040 P28482 MAP kinase ERK2 81.72% 83.82%
CHEMBL3401 O75469 Pregnane X receptor 80.49% 94.73%

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 102000781
LOTUS LTS0064392
wikiData Q105126499