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(1S,2R,6S,7R,9R,11R,12R,15S,16S)-15-[(1S)-1-[(2S)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,12,15-trihydroxy-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 2b42d1b0-005c-4e40-938c-7c21cda1771a
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1S,2R,6S,7R,9R,11R,12R,15S,16S)-15-[(1S)-1-[(2S)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,12,15-trihydroxy-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=CC6O)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]6O)C)O5)C)O)O)O)C
InChI InChI=1S/C28H38O8/c1-14-12-20(35-22(31)15(14)2)25(5,32)27(34)11-10-26(33)17-13-21-28(36-21)19(30)7-6-18(29)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-17,19-21,30,32-34H,8-13H2,1-5H3/t16-,17+,19-,20-,21+,23-,24-,25-,26+,27-,28+/m0/s1
InChI Key UPBUGICUKQIKTJ-VQDSAXESSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C28H38O8
Molecular Weight 502.60 g/mol
Exact Mass 502.25666817 g/mol
Topological Polar Surface Area (TPSA) 137.00 Ų
XlogP 0.60
Atomic LogP (AlogP) 1.73
H-Bond Acceptor 8
H-Bond Donor 4
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,2R,6S,7R,9R,11R,12R,15S,16S)-15-[(1S)-1-[(2S)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,12,15-trihydroxy-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 + 0.8604 86.04%
Caco-2 - 0.7133 71.33%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.6273 62.73%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8710 87.10%
OATP1B3 inhibitior + 0.9400 94.00%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6374 63.74%
BSEP inhibitior + 0.7216 72.16%
P-glycoprotein inhibitior - 0.4612 46.12%
P-glycoprotein substrate + 0.5949 59.49%
CYP3A4 substrate + 0.7206 72.06%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8924 89.24%
CYP3A4 inhibition - 0.7750 77.50%
CYP2C9 inhibition - 0.8408 84.08%
CYP2C19 inhibition - 0.8738 87.38%
CYP2D6 inhibition - 0.9484 94.84%
CYP1A2 inhibition - 0.8267 82.67%
CYP2C8 inhibition + 0.5380 53.80%
CYP inhibitory promiscuity - 0.9803 98.03%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5958 59.58%
Eye corrosion - 0.9902 99.02%
Eye irritation - 0.9382 93.82%
Skin irritation + 0.5274 52.74%
Skin corrosion - 0.9055 90.55%
Ames mutagenesis - 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7005 70.05%
Micronuclear - 0.7000 70.00%
Hepatotoxicity + 0.6232 62.32%
skin sensitisation - 0.8271 82.71%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8875 88.75%
Nephrotoxicity + 0.8272 82.72%
Acute Oral Toxicity (c) I 0.3666 36.66%
Estrogen receptor binding + 0.8301 83.01%
Androgen receptor binding + 0.7737 77.37%
Thyroid receptor binding + 0.6106 61.06%
Glucocorticoid receptor binding + 0.7450 74.50%
Aromatase binding + 0.7925 79.25%
PPAR gamma + 0.6245 62.45%
Honey bee toxicity - 0.8040 80.40%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity + 0.6300 63.00%
Fish aquatic toxicity + 0.9759 97.59%

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 97.64% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.58% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.29% 95.56%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 91.69% 97.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.26% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.59% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.43% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.25% 86.33%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 86.61% 93.04%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.46% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.64% 89.00%
CHEMBL1871 P10275 Androgen Receptor 85.57% 96.43%
CHEMBL3359 P21462 Formyl peptide receptor 1 85.20% 93.56%
CHEMBL2581 P07339 Cathepsin D 84.27% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.12% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 83.54% 82.69%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 82.83% 100.00%
CHEMBL218 P21554 Cannabinoid CB1 receptor 82.22% 96.61%
CHEMBL1902 P62942 FK506-binding protein 1A 81.36% 97.05%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 80.37% 91.03%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 80.07% 90.93%

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 156017944
LOTUS LTS0183150
wikiData Q105276701