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(1S,2R,6S,7S,9R,11R,12R,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-12,15-dihydroxy-6-methoxy-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 3989769b-0ada-4885-a56d-b3df49410931
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1S,2R,6S,7S,9R,11R,12R,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-12,15-dihydroxy-6-methoxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)(C2(CCC3(C2(CCC4C3CC5C6(C4(C(=O)C=CC6OC)C)O5)C)O)O)O)C
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]3C[C@@H]5[C@]6([C@@]4(C(=O)C=C[C@@H]6OC)C)O5)C)O)O)O)C
InChI InChI=1S/C29H40O8/c1-15-13-21(36-23(31)16(15)2)26(5,32)28(34)12-11-27(33)18-14-22-29(37-22)20(35-6)8-7-19(30)25(29,4)17(18)9-10-24(27,28)3/h7-8,17-18,20-22,32-34H,9-14H2,1-6H3/t17-,18+,20-,21+,22+,24-,25-,26+,27+,28-,29+/m0/s1
InChI Key NQRCUXGSABTIEO-PWQNOUFCSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H40O8
Molecular Weight 516.60 g/mol
Exact Mass 516.27231823 g/mol
Topological Polar Surface Area (TPSA) 126.00 Ų
XlogP 1.20
Atomic LogP (AlogP) 2.38
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 (1S,2R,6S,7S,9R,11R,12R,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-12,15-dihydroxy-6-methoxy-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 + 0.8534 85.34%
Caco-2 - 0.7164 71.64%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability + 0.5714 57.14%
Subcellular localzation Mitochondria 0.6047 60.47%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8723 87.23%
OATP1B3 inhibitior + 0.9401 94.01%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7124 71.24%
BSEP inhibitior + 0.8399 83.99%
P-glycoprotein inhibitior + 0.6364 63.64%
P-glycoprotein substrate + 0.5942 59.42%
CYP3A4 substrate + 0.7273 72.73%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8958 89.58%
CYP3A4 inhibition - 0.7984 79.84%
CYP2C9 inhibition - 0.7857 78.57%
CYP2C19 inhibition - 0.8353 83.53%
CYP2D6 inhibition - 0.9371 93.71%
CYP1A2 inhibition - 0.8077 80.77%
CYP2C8 inhibition + 0.6241 62.41%
CYP inhibitory promiscuity - 0.9700 97.00%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6226 62.26%
Eye corrosion - 0.9891 98.91%
Eye irritation - 0.9211 92.11%
Skin irritation - 0.5593 55.93%
Skin corrosion - 0.9175 91.75%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7494 74.94%
Micronuclear - 0.6300 63.00%
Hepatotoxicity + 0.6285 62.85%
skin sensitisation - 0.8464 84.64%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.8875 88.75%
Nephrotoxicity + 0.8193 81.93%
Acute Oral Toxicity (c) I 0.3261 32.61%
Estrogen receptor binding + 0.8070 80.70%
Androgen receptor binding + 0.7776 77.76%
Thyroid receptor binding + 0.6061 60.61%
Glucocorticoid receptor binding + 0.7255 72.55%
Aromatase binding + 0.7764 77.64%
PPAR gamma + 0.6498 64.98%
Honey bee toxicity - 0.7572 75.72%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.7000 70.00%
Fish aquatic toxicity + 0.9604 96.04%

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 98.08% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.74% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.56% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.16% 91.11%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 92.71% 97.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.82% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.71% 86.33%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 89.82% 93.04%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.42% 99.23%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.69% 95.89%
CHEMBL1871 P10275 Androgen Receptor 87.37% 96.43%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.38% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.71% 89.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 84.58% 91.07%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.48% 94.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 84.36% 93.56%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 82.97% 100.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.83% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 82.78% 82.69%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 82.28% 97.33%
CHEMBL1902 P62942 FK506-binding protein 1A 82.24% 97.05%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 81.61% 91.03%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.47% 92.62%

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 162923559
LOTUS LTS0246752
wikiData Q105184054