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(1R,2R,6S,7R,9R,11S,12R,15S,16S)-6,12,15-trihydroxy-15-[(1S)-1-hydroxy-1-[(2S)-4-(hydroxymethyl)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-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 57040236-173b-4ed2-9fba-7e00a02b7887
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1R,2R,6S,7R,9R,11S,12R,15S,16S)-6,12,15-trihydroxy-15-[(1S)-1-hydroxy-1-[(2S)-4-(hydroxymethyl)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
SMILES (Canonical) CC1=C(CC(OC1=O)C(C)(C2(CCC3(C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)O)O)O)CO
SMILES (Isomeric) CC1=C(C[C@H](OC1=O)[C@@](C)([C@@]2(CC[C@@]3([C@@]2(CC[C@@H]4[C@@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=C[C@@H]6O)C)O5)C)O)O)O)CO
InChI InChI=1S/C28H38O9/c1-14-15(13-29)11-20(36-22(14)32)25(4,33)27(35)10-9-26(34)17-12-21-28(37-21)19(31)6-5-18(30)24(28,3)16(17)7-8-23(26,27)2/h5-6,16-17,19-21,29,31,33-35H,7-13H2,1-4H3/t16-,17+,19+,20+,21-,23+,24+,25+,26-,27+,28-/m1/s1
InChI Key NXTIQWCWEAVYTK-DQCUCAMCSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H38O9
Molecular Weight 518.60 g/mol
Exact Mass 518.25158279 g/mol
Topological Polar Surface Area (TPSA) 157.00 Ų
XlogP -0.60
Atomic LogP (AlogP) 0.70
H-Bond Acceptor 9
H-Bond Donor 5
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,2R,6S,7R,9R,11S,12R,15S,16S)-6,12,15-trihydroxy-15-[(1S)-1-hydroxy-1-[(2S)-4-(hydroxymethyl)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-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 + 0.7922 79.22%
Caco-2 - 0.7552 75.52%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7080 70.80%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8628 86.28%
OATP1B3 inhibitior + 0.9398 93.98%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6079 60.79%
BSEP inhibitior + 0.6471 64.71%
P-glycoprotein inhibitior - 0.4512 45.12%
P-glycoprotein substrate + 0.6497 64.97%
CYP3A4 substrate + 0.7279 72.79%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8927 89.27%
CYP3A4 inhibition - 0.8046 80.46%
CYP2C9 inhibition - 0.8144 81.44%
CYP2C19 inhibition - 0.9091 90.91%
CYP2D6 inhibition - 0.9471 94.71%
CYP1A2 inhibition - 0.8870 88.70%
CYP2C8 inhibition + 0.5866 58.66%
CYP inhibitory promiscuity - 0.9724 97.24%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6422 64.22%
Eye corrosion - 0.9895 98.95%
Eye irritation - 0.9419 94.19%
Skin irritation + 0.5199 51.99%
Skin corrosion - 0.9332 93.32%
Ames mutagenesis - 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6508 65.08%
Micronuclear - 0.7300 73.00%
Hepatotoxicity + 0.5908 59.08%
skin sensitisation - 0.8947 89.47%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity + 0.6750 67.50%
Acute Oral Toxicity (c) I 0.5389 53.89%
Estrogen receptor binding + 0.8139 81.39%
Androgen receptor binding + 0.7697 76.97%
Thyroid receptor binding + 0.5841 58.41%
Glucocorticoid receptor binding + 0.7290 72.90%
Aromatase binding + 0.7568 75.68%
PPAR gamma + 0.5997 59.97%
Honey bee toxicity - 0.8125 81.25%
Biodegradation - 0.9500 95.00%
Crustacea aquatic toxicity + 0.5900 59.00%
Fish aquatic toxicity + 0.9551 95.51%

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 97.73% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.42% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.32% 95.56%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 92.23% 97.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.12% 97.09%
CHEMBL204 P00734 Thrombin 91.56% 96.01%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 90.16% 91.11%
CHEMBL2581 P07339 Cathepsin D 89.45% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.51% 86.33%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 88.34% 82.69%
CHEMBL1871 P10275 Androgen Receptor 87.51% 96.43%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.34% 95.89%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 85.97% 96.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 85.56% 96.61%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 84.81% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.69% 99.23%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.51% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 82.95% 93.04%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.90% 92.62%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.63% 89.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.53% 91.07%
CHEMBL2996 Q05655 Protein kinase C delta 82.33% 97.79%
CHEMBL1907 P15144 Aminopeptidase N 81.35% 93.31%
CHEMBL259 P32245 Melanocortin receptor 4 80.10% 95.38%

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 viscosa

Cross-Links

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PubChem 162988759
LOTUS LTS0035174
wikiData Q105187321