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(1S,2R,7S,9R,11R,12R,16R)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-12-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-14-en-3-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 0076881b-c75a-4a72-a6d6-86bb313f6287
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1S,2R,7S,9R,11R,12R,16R)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-12-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-14-en-3-one
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C28H38O6/c1-15-13-21(33-23(30)16(15)2)26(5,31)19-9-12-27(32)18-14-22-28(34-22)10-6-7-20(29)25(28,4)17(18)8-11-24(19,27)3/h9,17-18,21-22,31-32H,6-8,10-14H2,1-5H3/t17-,18+,21+,22+,24+,25-,26+,27+,28+/m0/s1
InChI Key DGQQSGDPWKERCQ-QJFLRJBQSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C28H38O6
Molecular Weight 470.60 g/mol
Exact Mass 470.26683893 g/mol
Topological Polar Surface Area (TPSA) 96.40 Ų
XlogP 2.10
Atomic LogP (AlogP) 3.78
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,2R,7S,9R,11R,12R,16R)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-12-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-14-en-3-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9576 95.76%
Caco-2 - 0.5361 53.61%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability + 0.5143 51.43%
Subcellular localzation Mitochondria 0.6830 68.30%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8642 86.42%
OATP1B3 inhibitior + 0.9189 91.89%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.6374 63.74%
BSEP inhibitior + 0.9006 90.06%
P-glycoprotein inhibitior + 0.5987 59.87%
P-glycoprotein substrate + 0.5655 56.55%
CYP3A4 substrate + 0.7117 71.17%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9004 90.04%
CYP3A4 inhibition - 0.7609 76.09%
CYP2C9 inhibition - 0.8586 85.86%
CYP2C19 inhibition - 0.8921 89.21%
CYP2D6 inhibition - 0.9560 95.60%
CYP1A2 inhibition - 0.7538 75.38%
CYP2C8 inhibition + 0.6250 62.50%
CYP inhibitory promiscuity - 0.9760 97.60%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5461 54.61%
Eye corrosion - 0.9917 99.17%
Eye irritation - 0.9371 93.71%
Skin irritation + 0.5729 57.29%
Skin corrosion - 0.9051 90.51%
Ames mutagenesis - 0.6700 67.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4459 44.59%
Micronuclear - 0.6900 69.00%
Hepatotoxicity - 0.5414 54.14%
skin sensitisation - 0.8195 81.95%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9250 92.50%
Nephrotoxicity + 0.6655 66.55%
Acute Oral Toxicity (c) I 0.4368 43.68%
Estrogen receptor binding + 0.7654 76.54%
Androgen receptor binding + 0.7501 75.01%
Thyroid receptor binding + 0.5384 53.84%
Glucocorticoid receptor binding + 0.8144 81.44%
Aromatase binding + 0.7821 78.21%
PPAR gamma + 0.6337 63.37%
Honey bee toxicity - 0.8181 81.81%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6400 64.00%
Fish aquatic toxicity + 0.9780 97.80%

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 99.32% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.13% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.41% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 93.95% 99.23%
CHEMBL241 Q14432 Phosphodiesterase 3A 92.27% 92.94%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 90.98% 91.11%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.49% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.33% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.00% 97.09%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 89.22% 93.04%
CHEMBL2039 P27338 Monoamine oxidase B 88.97% 92.51%
CHEMBL1951 P21397 Monoamine oxidase A 88.81% 91.49%
CHEMBL3359 P21462 Formyl peptide receptor 1 87.57% 93.56%
CHEMBL2996 Q05655 Protein kinase C delta 86.74% 97.79%
CHEMBL1937 Q92769 Histone deacetylase 2 86.72% 94.75%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.35% 97.14%
CHEMBL1871 P10275 Androgen Receptor 85.37% 96.43%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.85% 94.00%
CHEMBL218 P21554 Cannabinoid CB1 receptor 84.49% 96.61%
CHEMBL3401 O75469 Pregnane X receptor 84.39% 94.73%
CHEMBL1902 P62942 FK506-binding protein 1A 84.32% 97.05%
CHEMBL2581 P07339 Cathepsin D 82.58% 98.95%
CHEMBL5028 O14672 ADAM10 81.85% 97.50%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.93% 82.69%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.82% 89.00%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 80.27% 97.33%
CHEMBL5103 Q969S8 Histone deacetylase 10 80.26% 90.08%

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.
Physalis angulata

Cross-Links

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PubChem 102471221
LOTUS LTS0163537
wikiData Q104979140