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(1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-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 e443ac40-1074-4a54-b752-d30c98ec93ad
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3C5C(O5)C6(C4(C(=O)C=CC6)C)O)C)O)C
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@](C)([C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3[C@H]5[C@H](O5)[C@@]6([C@@]4(C(=O)C=CC6)C)O)C)O)C
InChI InChI=1S/C28H38O6/c1-14-13-20(33-24(30)15(14)2)27(5,31)18-9-8-16-21-17(10-12-25(16,18)3)26(4)19(29)7-6-11-28(26,32)23-22(21)34-23/h6-7,16-18,20-23,31-32H,8-13H2,1-5H3/t16-,17-,18-,20+,21-,22-,23-,25-,26-,27-,28-/m0/s1
InChI Key DXWHOKCXBGLTMQ-KEWGCLRWSA-N
Popularity 1 reference 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 3.30
Atomic LogP (AlogP) 3.50
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,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-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 - 0.6006 60.06%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.6830 68.30%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8936 89.36%
OATP1B3 inhibitior + 0.9189 91.89%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6374 63.74%
BSEP inhibitior + 0.8614 86.14%
P-glycoprotein inhibitior + 0.6554 65.54%
P-glycoprotein substrate - 0.5398 53.98%
CYP3A4 substrate + 0.7302 73.02%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9069 90.69%
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 - 0.5827 58.27%
CYP inhibitory promiscuity - 0.9760 97.60%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5461 54.61%
Eye corrosion - 0.9917 99.17%
Eye irritation - 0.9434 94.34%
Skin irritation + 0.5729 57.29%
Skin corrosion - 0.9051 90.51%
Ames mutagenesis - 0.6883 68.83%
Human Ether-a-go-go-Related Gene inhibition + 0.7572 75.72%
Micronuclear - 0.6900 69.00%
Hepatotoxicity + 0.6250 62.50%
skin sensitisation - 0.8195 81.95%
Respiratory toxicity + 0.8556 85.56%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9250 92.50%
Nephrotoxicity + 0.6092 60.92%
Acute Oral Toxicity (c) I 0.4368 43.68%
Estrogen receptor binding + 0.8369 83.69%
Androgen receptor binding + 0.7563 75.63%
Thyroid receptor binding + 0.6553 65.53%
Glucocorticoid receptor binding + 0.7330 73.30%
Aromatase binding + 0.7475 74.75%
PPAR gamma + 0.6552 65.52%
Honey bee toxicity - 0.8606 86.06%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.6600 66.00%
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 97.11% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.80% 85.14%
CHEMBL4040 P28482 MAP kinase ERK2 94.70% 83.82%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.58% 95.56%
CHEMBL230 P35354 Cyclooxygenase-2 93.58% 89.63%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 92.04% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.70% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.59% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.93% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.89% 89.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 87.65% 91.11%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 87.51% 93.04%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 87.23% 93.40%
CHEMBL1937 Q92769 Histone deacetylase 2 87.17% 94.75%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 86.14% 90.93%
CHEMBL1871 P10275 Androgen Receptor 85.27% 96.43%
CHEMBL3359 P21462 Formyl peptide receptor 1 85.15% 93.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.42% 95.89%
CHEMBL3401 O75469 Pregnane X receptor 83.91% 94.73%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.90% 97.09%

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 44576308
LOTUS LTS0164394
wikiData Q104991227