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(2S)-2-[(1S)-1-[(8R,9S,10R,13S,14R,17S)-14,17-dihydroxy-10,13-dimethyl-1-oxo-2,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-5-(hydroxymethyl)-4-methyl-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 bf7e3ae0-6855-4c7b-ab41-9584acbb943f
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2S)-2-[(1S)-1-[(8R,9S,10R,13S,14R,17S)-14,17-dihydroxy-10,13-dimethyl-1-oxo-2,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)(C2(CCC3(C2(CCC4C3CC=C5C4(C(=O)CC=C5)C)C)O)O)O)CO
SMILES (Isomeric) CC1=C(C(=O)O[C@@H](C1)[C@@](C)([C@@]2(CC[C@@]3([C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(C(=O)CC=C5)C)C)O)O)O)CO
InChI InChI=1S/C28H38O7/c1-16-14-22(35-23(31)18(16)15-29)26(4,32)28(34)13-12-27(33)20-9-8-17-6-5-7-21(30)25(17,3)19(20)10-11-24(27,28)2/h5-6,8,19-20,22,29,32-34H,7,9-15H2,1-4H3/t19-,20+,22-,24-,25-,26-,27+,28-/m0/s1
InChI Key BAIDVXUGHJDBOO-MXKUFHJFSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H38O7
Molecular Weight 486.60 g/mol
Exact Mass 486.26175355 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP 1.60
Atomic LogP (AlogP) 2.52
H-Bond Acceptor 7
H-Bond Donor 4
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S)-2-[(1S)-1-[(8R,9S,10R,13S,14R,17S)-14,17-dihydroxy-10,13-dimethyl-1-oxo-2,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-5-(hydroxymethyl)-4-methyl-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 + 0.8651 86.51%
Caco-2 - 0.6481 64.81%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability + 0.5429 54.29%
Subcellular localzation Mitochondria 0.8215 82.15%
OATP2B1 inhibitior - 0.8646 86.46%
OATP1B1 inhibitior + 0.8788 87.88%
OATP1B3 inhibitior + 0.8868 88.68%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.5438 54.38%
BSEP inhibitior + 0.8461 84.61%
P-glycoprotein inhibitior + 0.5736 57.36%
P-glycoprotein substrate + 0.5758 57.58%
CYP3A4 substrate + 0.7034 70.34%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9118 91.18%
CYP3A4 inhibition - 0.7935 79.35%
CYP2C9 inhibition - 0.9249 92.49%
CYP2C19 inhibition - 0.9334 93.34%
CYP2D6 inhibition - 0.9552 95.52%
CYP1A2 inhibition - 0.8935 89.35%
CYP2C8 inhibition + 0.5355 53.55%
CYP inhibitory promiscuity - 0.9669 96.69%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6405 64.05%
Eye corrosion - 0.9916 99.16%
Eye irritation - 0.9582 95.82%
Skin irritation + 0.6554 65.54%
Skin corrosion - 0.9384 93.84%
Ames mutagenesis - 0.7000 70.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3641 36.41%
Micronuclear - 0.8100 81.00%
Hepatotoxicity + 0.6750 67.50%
skin sensitisation - 0.9323 93.23%
Respiratory toxicity + 0.7667 76.67%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8375 83.75%
Nephrotoxicity + 0.8136 81.36%
Acute Oral Toxicity (c) III 0.6536 65.36%
Estrogen receptor binding + 0.8469 84.69%
Androgen receptor binding + 0.7634 76.34%
Thyroid receptor binding + 0.6495 64.95%
Glucocorticoid receptor binding + 0.8119 81.19%
Aromatase binding + 0.7866 78.66%
PPAR gamma + 0.5901 59.01%
Honey bee toxicity - 0.8530 85.30%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.6200 62.00%
Fish aquatic toxicity + 0.9614 96.14%

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 98.95% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.92% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.32% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.71% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.23% 86.33%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 88.11% 93.04%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.61% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 86.47% 94.73%
CHEMBL2581 P07339 Cathepsin D 85.97% 98.95%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 85.20% 93.03%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.88% 100.00%
CHEMBL2996 Q05655 Protein kinase C delta 84.74% 97.79%
CHEMBL3192 Q9BY41 Histone deacetylase 8 84.54% 93.99%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 84.22% 82.69%
CHEMBL1907 P15144 Aminopeptidase N 84.12% 93.31%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.91% 97.14%
CHEMBL3359 P21462 Formyl peptide receptor 1 83.73% 93.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.72% 94.00%
CHEMBL3310 Q96DB2 Histone deacetylase 11 83.33% 88.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 82.01% 96.09%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.33% 92.62%
CHEMBL5103 Q969S8 Histone deacetylase 10 81.07% 90.08%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.81% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.56% 89.00%

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.
Ajuga parviflora

Cross-Links

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PubChem 163007687
LOTUS LTS0114421
wikiData Q104922190