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(1S,2S,4S,5R,10R,11S,14R,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5,15,18-trihydroxy-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 84027900-94ea-4a3f-9c59-85398268ddf6
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1S,2S,4S,5R,10R,11S,14R,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5,15,18-trihydroxy-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)C2(CCC3(C2(CCC4C3C5C(O5)C6(C4(C(=O)C=CC6)C)O)C)O)O)C
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@]2(CC[C@]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)O)C
InChI InChI=1S/C28H38O7/c1-14-13-18(34-23(30)15(14)2)16(3)26(31)11-12-27(32)20-17(8-10-24(26,27)4)25(5)19(29)7-6-9-28(25,33)22-21(20)35-22/h6-7,16-18,20-22,31-33H,8-13H2,1-5H3/t16-,17+,18-,20+,21+,22+,24-,25+,26+,27+,28+/m1/s1
InChI Key GRKSPXDGNSOVDH-XNZPLHLSSA-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 2.00
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,2S,4S,5R,10R,11S,14R,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5,15,18-trihydroxy-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 + 0.9210 92.10%
Caco-2 - 0.6671 66.71%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.6125 61.25%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8762 87.62%
OATP1B3 inhibitior + 0.9446 94.46%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6624 66.24%
BSEP inhibitior + 0.8915 89.15%
P-glycoprotein inhibitior + 0.6101 61.01%
P-glycoprotein substrate - 0.5338 53.38%
CYP3A4 substrate + 0.6893 68.93%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9069 90.69%
CYP3A4 inhibition - 0.7764 77.64%
CYP2C9 inhibition - 0.8514 85.14%
CYP2C19 inhibition - 0.8969 89.69%
CYP2D6 inhibition - 0.9506 95.06%
CYP1A2 inhibition - 0.8148 81.48%
CYP2C8 inhibition + 0.4444 44.44%
CYP inhibitory promiscuity - 0.9685 96.85%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5832 58.32%
Eye corrosion - 0.9908 99.08%
Eye irritation - 0.9412 94.12%
Skin irritation + 0.5409 54.09%
Skin corrosion - 0.9050 90.50%
Ames mutagenesis - 0.6353 63.53%
Human Ether-a-go-go-Related Gene inhibition + 0.7057 70.57%
Micronuclear - 0.6900 69.00%
Hepatotoxicity + 0.5875 58.75%
skin sensitisation - 0.8269 82.69%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity + 0.7159 71.59%
Acute Oral Toxicity (c) I 0.4048 40.48%
Estrogen receptor binding + 0.8638 86.38%
Androgen receptor binding + 0.7585 75.85%
Thyroid receptor binding + 0.6432 64.32%
Glucocorticoid receptor binding + 0.7082 70.82%
Aromatase binding + 0.7542 75.42%
PPAR gamma + 0.6378 63.78%
Honey bee toxicity - 0.8082 80.82%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9729 97.29%

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 96.26% 85.14%
CHEMBL4040 P28482 MAP kinase ERK2 96.13% 83.82%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.59% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.24% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.56% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.94% 96.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.79% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.44% 99.23%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 90.43% 97.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.99% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.75% 86.33%
CHEMBL2581 P07339 Cathepsin D 86.67% 98.95%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 86.45% 93.04%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.55% 95.89%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 84.79% 94.80%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 83.27% 86.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.83% 93.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.38% 97.09%
CHEMBL1937 Q92769 Histone deacetylase 2 81.95% 94.75%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.79% 94.45%

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 163019134
LOTUS LTS0264857
wikiData Q105016154