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(1S,2R,6S,7R,9R,11R,12R,15S,16R)-15-[(1R)-1-[(2S)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,12-dihydroxy-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 d6f81f50-6aff-474b-8af4-2f349a9421ab
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,16R)-15-[(1R)-1-[(2S)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,12-dihydroxy-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)(C2CCC3(C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)O)O)C
SMILES (Isomeric) CC1=C(C(=O)O[C@@H](C1)[C@@](C)([C@H]2CC[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)C
InChI InChI=1S/C28H38O7/c1-14-12-21(34-23(31)15(14)2)26(5,32)18-9-11-27(33)17-13-22-28(35-22)20(30)7-6-19(29)25(28,4)16(17)8-10-24(18,27)3/h6-7,16-18,20-22,30,32-33H,8-13H2,1-5H3/t16-,17+,18-,20-,21-,22+,24+,25-,26+,27+,28+/m0/s1
InChI Key IYJCHCJFKFPISJ-OSRZGQGSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H38O7
Molecular Weight 486.60 g/mol
Exact Mass 486.26175355 g/mol
Topological Polar Surface Area (TPSA) 117.00 Ų
XlogP 1.70
Atomic LogP (AlogP) 2.61
H-Bond Acceptor 7
H-Bond Donor 3
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,16R)-15-[(1R)-1-[(2S)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,12-dihydroxy-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 + 0.9576 95.76%
Caco-2 - 0.6452 64.52%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.5000 50.00%
Subcellular localzation Mitochondria 0.6830 68.30%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8447 84.47%
OATP1B3 inhibitior + 0.9189 91.89%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6374 63.74%
BSEP inhibitior + 0.8129 81.29%
P-glycoprotein inhibitior - 0.4769 47.69%
P-glycoprotein substrate + 0.5394 53.94%
CYP3A4 substrate + 0.7328 73.28%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8956 89.56%
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 + 0.5465 54.65%
CYP inhibitory promiscuity - 0.9760 97.60%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5461 54.61%
Eye corrosion - 0.9917 99.17%
Eye irritation - 0.9490 94.90%
Skin irritation + 0.5729 57.29%
Skin corrosion - 0.9051 90.51%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3665 36.65%
Micronuclear - 0.6900 69.00%
Hepatotoxicity + 0.5431 54.31%
skin sensitisation - 0.8195 81.95%
Respiratory toxicity + 0.8333 83.33%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9250 92.50%
Nephrotoxicity + 0.7385 73.85%
Acute Oral Toxicity (c) I 0.4368 43.68%
Estrogen receptor binding + 0.8585 85.85%
Androgen receptor binding + 0.7638 76.38%
Thyroid receptor binding + 0.5756 57.56%
Glucocorticoid receptor binding + 0.7803 78.03%
Aromatase binding + 0.7939 79.39%
PPAR gamma + 0.5915 59.15%
Honey bee toxicity - 0.7901 79.01%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.6300 63.00%
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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.33% 85.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.35% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.51% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.34% 91.11%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 91.03% 97.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.68% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.30% 99.23%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 87.44% 82.69%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 86.43% 93.04%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.26% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.24% 95.89%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.38% 91.07%
CHEMBL1902 P62942 FK506-binding protein 1A 85.16% 97.05%
CHEMBL1871 P10275 Androgen Receptor 84.39% 96.43%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.39% 100.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 83.38% 93.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.93% 89.00%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 82.77% 100.00%
CHEMBL2581 P07339 Cathepsin D 80.85% 98.95%

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.
Withania somnifera

Cross-Links

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PubChem 162969225
LOTUS LTS0200004
wikiData Q105122774