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(2S,5R,9R,10R,13R,14R,17S)-17-[(1R)-1-[(2R)-4-ethyl-5-methyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-2,14-dihydroxy-10,13-dimethyl-2,4,5,9,11,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,6,12-trione

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 e7622b2e-075c-4870-88e5-382d7ea9eba2
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2S,5R,9R,10R,13R,14R,17S)-17-[(1R)-1-[(2R)-4-ethyl-5-methyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-2,14-dihydroxy-10,13-dimethyl-2,4,5,9,11,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,6,12-trione
SMILES (Canonical) CCC1=C(C(=O)OC(C1)C(C)(C2CCC3(C2(C(=O)CC4C3=CC(=O)C5C4(CC(C(=O)C5)O)C)C)O)O)C
SMILES (Isomeric) CCC1=C(C(=O)O[C@H](C1)[C@@](C)([C@H]2CC[C@@]3([C@@]2(C(=O)C[C@H]4C3=CC(=O)[C@H]5[C@@]4(C[C@@H](C(=O)C5)O)C)C)O)O)C
InChI InChI=1S/C29H38O8/c1-6-15-9-24(37-25(34)14(15)2)28(5,35)22-7-8-29(36)17-10-19(30)18-11-20(31)21(32)13-26(18,3)16(17)12-23(33)27(22,29)4/h10,16,18,21-22,24,32,35-36H,6-9,11-13H2,1-5H3/t16-,18-,21-,22-,24+,26+,27-,28+,29+/m0/s1
InChI Key XESXXIRWMOUPNF-LLAOVTOUSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H38O8
Molecular Weight 514.60 g/mol
Exact Mass 514.25666817 g/mol
Topological Polar Surface Area (TPSA) 138.00 Ų
XlogP 0.20
Atomic LogP (AlogP) 2.37
H-Bond Acceptor 8
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,5R,9R,10R,13R,14R,17S)-17-[(1R)-1-[(2R)-4-ethyl-5-methyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-2,14-dihydroxy-10,13-dimethyl-2,4,5,9,11,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,6,12-trione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9836 98.36%
Caco-2 - 0.6639 66.39%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.7342 73.42%
OATP2B1 inhibitior - 0.8564 85.64%
OATP1B1 inhibitior + 0.8749 87.49%
OATP1B3 inhibitior + 0.9226 92.26%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior + 0.7183 71.83%
P-glycoprotein inhibitior + 0.5834 58.34%
P-glycoprotein substrate + 0.6277 62.77%
CYP3A4 substrate + 0.7118 71.18%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9083 90.83%
CYP3A4 inhibition + 0.5885 58.85%
CYP2C9 inhibition - 0.9216 92.16%
CYP2C19 inhibition - 0.8578 85.78%
CYP2D6 inhibition - 0.9484 94.84%
CYP1A2 inhibition - 0.8881 88.81%
CYP2C8 inhibition + 0.5616 56.16%
CYP inhibitory promiscuity - 0.9202 92.02%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5756 57.56%
Eye corrosion - 0.9938 99.38%
Eye irritation - 0.9278 92.78%
Skin irritation + 0.7632 76.32%
Skin corrosion - 0.9185 91.85%
Ames mutagenesis - 0.6154 61.54%
Human Ether-a-go-go-Related Gene inhibition - 0.5407 54.07%
Micronuclear - 0.7700 77.00%
Hepatotoxicity + 0.5837 58.37%
skin sensitisation - 0.8728 87.28%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9778 97.78%
Mitochondrial toxicity + 0.9500 95.00%
Nephrotoxicity - 0.6548 65.48%
Acute Oral Toxicity (c) I 0.3087 30.87%
Estrogen receptor binding + 0.7849 78.49%
Androgen receptor binding + 0.7501 75.01%
Thyroid receptor binding + 0.5197 51.97%
Glucocorticoid receptor binding + 0.7986 79.86%
Aromatase binding + 0.7306 73.06%
PPAR gamma + 0.5868 58.68%
Honey bee toxicity - 0.8550 85.50%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5900 59.00%
Fish aquatic toxicity + 0.9887 98.87%

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 98.76% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.00% 85.14%
CHEMBL2581 P07339 Cathepsin D 93.17% 98.95%
CHEMBL218 P21554 Cannabinoid CB1 receptor 93.10% 96.61%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.67% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.56% 91.11%
CHEMBL3192 Q9BY41 Histone deacetylase 8 89.72% 93.99%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.53% 95.56%
CHEMBL230 P35354 Cyclooxygenase-2 88.35% 89.63%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.77% 96.09%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 87.73% 92.62%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 87.28% 82.69%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.75% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.97% 86.33%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.88% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.14% 100.00%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 83.54% 94.78%
CHEMBL1902 P62942 FK506-binding protein 1A 83.45% 97.05%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.91% 92.94%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 80.64% 97.33%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.13% 94.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.12% 93.56%

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.
Ajuga reptans

Cross-Links

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PubChem 163081660
LOTUS LTS0182973
wikiData Q105326593