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(1S,2S,4S,5R,10R,11S,14R,15S,18R)-5,15,18-trihydroxy-15-[(1R)-1-[(2S,3S)-3-hydroxy-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-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 2e494655-c815-4286-ac94-beadb8f9c6ab
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,18R)-5,15,18-trihydroxy-15-[(1R)-1-[(2S,3S)-3-hydroxy-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-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(C1O)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]([C@H]1O)[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/C28H38O8/c1-13-14(2)23(31)36-20(19(13)30)15(3)26(32)11-12-27(33)18-16(8-10-24(26,27)4)25(5)17(29)7-6-9-28(25,34)22-21(18)35-22/h6-7,15-16,18-22,30,32-34H,8-12H2,1-5H3/t15-,16+,18+,19+,20+,21+,22+,24-,25+,26+,27-,28+/m1/s1
InChI Key GIGKYZWBLHTEDX-BZUVILJDSA-N
Popularity 0 references 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 0.90
Atomic LogP (AlogP) 1.58
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,2S,4S,5R,10R,11S,14R,15S,18R)-5,15,18-trihydroxy-15-[(1R)-1-[(2S,3S)-3-hydroxy-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-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 - 0.7311 73.11%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.6125 61.25%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8794 87.94%
OATP1B3 inhibitior + 0.9446 94.46%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6624 66.24%
BSEP inhibitior + 0.7555 75.55%
P-glycoprotein inhibitior - 0.4578 45.78%
P-glycoprotein substrate - 0.5284 52.84%
CYP3A4 substrate + 0.6983 69.83%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9032 90.32%
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 - 0.5733 57.33%
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 - 0.9385 93.85%
Skin irritation + 0.5409 54.09%
Skin corrosion - 0.9050 90.50%
Ames mutagenesis - 0.6707 67.07%
Human Ether-a-go-go-Related Gene inhibition - 0.3986 39.86%
Micronuclear - 0.6900 69.00%
Hepatotoxicity + 0.5750 57.50%
skin sensitisation - 0.8269 82.69%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity + 0.5462 54.62%
Acute Oral Toxicity (c) I 0.4048 40.48%
Estrogen receptor binding + 0.8440 84.40%
Androgen receptor binding + 0.7509 75.09%
Thyroid receptor binding + 0.5802 58.02%
Glucocorticoid receptor binding + 0.6748 67.48%
Aromatase binding + 0.7780 77.80%
PPAR gamma + 0.6164 61.64%
Honey bee toxicity - 0.7751 77.51%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.5100 51.00%
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 95.37% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.43% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.63% 97.25%
CHEMBL4040 P28482 MAP kinase ERK2 92.93% 83.82%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.02% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.96% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.28% 89.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 89.16% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.09% 100.00%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 88.05% 96.38%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.15% 94.45%
CHEMBL2581 P07339 Cathepsin D 86.90% 98.95%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.49% 99.23%
CHEMBL218 P21554 Cannabinoid CB1 receptor 86.16% 96.61%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.01% 86.33%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.37% 93.04%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 83.44% 90.71%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.09% 95.89%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.89% 97.09%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 80.88% 90.93%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.87% 92.62%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 80.28% 86.00%

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 163020162
LOTUS LTS0198637
wikiData Q104667845