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(2R)-2-[(1S)-1-[(4S,8S,9S,10R,13S,14S,17R)-4-hydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-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 dd4f084e-3435-4f0e-9a42-04098f6dff35
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1S)-1-[(4S,8S,9S,10R,13S,14S,17R)-4-hydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC=C5C4(C(=O)C=CC5O)C)C)CO
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(C(=O)C=C[C@@H]5O)C)C)CO
InChI InChI=1S/C28H38O5/c1-15-13-24(33-26(32)18(15)14-29)16(2)19-7-8-20-17-5-6-22-23(30)9-10-25(31)28(22,4)21(17)11-12-27(19,20)3/h6,9-10,16-17,19-21,23-24,29-30H,5,7-8,11-14H2,1-4H3/t16-,17-,19+,20-,21-,23-,24+,27+,28+/m0/s1
InChI Key SHDXNRZAYHPFMX-OBQFDWBNSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C28H38O5
Molecular Weight 454.60 g/mol
Exact Mass 454.27192431 g/mol
Topological Polar Surface Area (TPSA) 83.80 Ų
XlogP 4.50
Atomic LogP (AlogP) 4.14
H-Bond Acceptor 5
H-Bond Donor 2
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-[(4S,8S,9S,10R,13S,14S,17R)-4-hydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-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 + 0.9533 95.33%
Caco-2 - 0.6326 63.26%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability + 0.5714 57.14%
Subcellular localzation Mitochondria 0.8150 81.50%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8611 86.11%
OATP1B3 inhibitior + 0.9577 95.77%
MATE1 inhibitior - 0.9412 94.12%
OCT2 inhibitior + 0.5912 59.12%
BSEP inhibitior + 0.8800 88.00%
P-glycoprotein inhibitior + 0.6965 69.65%
P-glycoprotein substrate + 0.5651 56.51%
CYP3A4 substrate + 0.7307 73.07%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9069 90.69%
CYP3A4 inhibition - 0.6361 63.61%
CYP2C9 inhibition - 0.9464 94.64%
CYP2C19 inhibition - 0.9636 96.36%
CYP2D6 inhibition - 0.9576 95.76%
CYP1A2 inhibition - 0.6106 61.06%
CYP2C8 inhibition + 0.4810 48.10%
CYP inhibitory promiscuity - 0.8937 89.37%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5534 55.34%
Eye corrosion - 0.9920 99.20%
Eye irritation - 0.9762 97.62%
Skin irritation + 0.6693 66.93%
Skin corrosion - 0.9391 93.91%
Ames mutagenesis - 0.6114 61.14%
Human Ether-a-go-go-Related Gene inhibition - 0.3639 36.39%
Micronuclear - 0.8100 81.00%
Hepatotoxicity + 0.6030 60.30%
skin sensitisation - 0.9106 91.06%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity - 0.6902 69.02%
Acute Oral Toxicity (c) III 0.7020 70.20%
Estrogen receptor binding + 0.8171 81.71%
Androgen receptor binding + 0.7441 74.41%
Thyroid receptor binding + 0.6264 62.64%
Glucocorticoid receptor binding + 0.8746 87.46%
Aromatase binding + 0.6537 65.37%
PPAR gamma + 0.5993 59.93%
Honey bee toxicity - 0.8176 81.76%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9790 97.90%

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
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.60% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.27% 97.25%
CHEMBL2581 P07339 Cathepsin D 94.31% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.08% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 90.07% 91.11%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.86% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.03% 94.45%
CHEMBL5103 Q969S8 Histone deacetylase 10 86.96% 90.08%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.60% 97.09%
CHEMBL1937 Q92769 Histone deacetylase 2 86.29% 94.75%
CHEMBL221 P23219 Cyclooxygenase-1 83.57% 90.17%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.53% 95.89%
CHEMBL299 P17252 Protein kinase C alpha 83.42% 98.03%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.24% 97.14%
CHEMBL3192 Q9BY41 Histone deacetylase 8 82.90% 93.99%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 82.79% 90.71%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 82.34% 93.04%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 81.77% 93.03%
CHEMBL3310 Q96DB2 Histone deacetylase 11 81.54% 88.56%
CHEMBL3359 P21462 Formyl peptide receptor 1 81.04% 93.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.61% 94.00%
CHEMBL1871 P10275 Androgen Receptor 80.48% 96.43%
CHEMBL3401 O75469 Pregnane X receptor 80.13% 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.
Vassobia breviflora
Withania aristata
Withania somnifera

Cross-Links

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PubChem 90670439
LOTUS LTS0026960
wikiData Q105252911