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(1S,2R,5S,6S,7R,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R,4S,5R)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-6-hydroxy-5-methoxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-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 45b17567-01fc-43c8-9431-d5b69fc89c0b
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1S,2R,5S,6S,7R,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R,4S,5R)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-6-hydroxy-5-methoxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-3-one
SMILES (Canonical) CC1CC(OC(=O)C1C)C(C)(C2CCC3C2(CCC4C3CC5C6(C4(C(=O)CC(C6O)OC)C)O5)C)O
SMILES (Isomeric) C[C@H]1C[C@@H](OC(=O)[C@@H]1C)[C@@](C)([C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C[C@@H]([C@@H]6O)OC)C)O5)C)O
InChI InChI=1S/C29H44O7/c1-14-11-22(35-25(32)15(14)2)28(5,33)20-8-7-17-16-12-23-29(36-23)24(31)19(34-6)13-21(30)27(29,4)18(16)9-10-26(17,20)3/h14-20,22-24,31,33H,7-13H2,1-6H3/t14-,15+,16-,17-,18-,19-,20-,22+,23+,24-,26-,27-,28+,29-/m0/s1
InChI Key AFBUGKSTCXETMA-IHDABQKYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C29H44O7
Molecular Weight 504.70 g/mol
Exact Mass 504.30870374 g/mol
Topological Polar Surface Area (TPSA) 106.00 Ų
XlogP 3.20
Atomic LogP (AlogP) 3.28
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,2R,5S,6S,7R,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R,4S,5R)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-6-hydroxy-5-methoxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-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 + 0.8650 86.50%
Caco-2 - 0.7129 71.29%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability + 0.5571 55.71%
Subcellular localzation Mitochondria 0.7220 72.20%
OATP2B1 inhibitior - 0.7122 71.22%
OATP1B1 inhibitior + 0.8660 86.60%
OATP1B3 inhibitior + 0.8743 87.43%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7321 73.21%
BSEP inhibitior - 0.6970 69.70%
P-glycoprotein inhibitior + 0.5715 57.15%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.7562 75.62%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8451 84.51%
CYP3A4 inhibition - 0.8602 86.02%
CYP2C9 inhibition - 0.8478 84.78%
CYP2C19 inhibition - 0.8499 84.99%
CYP2D6 inhibition - 0.9525 95.25%
CYP1A2 inhibition - 0.6472 64.72%
CYP2C8 inhibition + 0.5377 53.77%
CYP inhibitory promiscuity - 0.9782 97.82%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6561 65.61%
Eye corrosion - 0.9898 98.98%
Eye irritation - 0.9425 94.25%
Skin irritation - 0.6290 62.90%
Skin corrosion - 0.9008 90.08%
Ames mutagenesis - 0.5854 58.54%
Human Ether-a-go-go-Related Gene inhibition - 0.4776 47.76%
Micronuclear - 0.7000 70.00%
Hepatotoxicity + 0.6533 65.33%
skin sensitisation - 0.8930 89.30%
Respiratory toxicity + 0.8333 83.33%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity + 0.4858 48.58%
Acute Oral Toxicity (c) I 0.3418 34.18%
Estrogen receptor binding + 0.6260 62.60%
Androgen receptor binding + 0.7778 77.78%
Thyroid receptor binding - 0.5828 58.28%
Glucocorticoid receptor binding + 0.7098 70.98%
Aromatase binding + 0.7107 71.07%
PPAR gamma + 0.6185 61.85%
Honey bee toxicity - 0.7159 71.59%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity + 0.6700 67.00%
Fish aquatic toxicity + 0.9232 92.32%

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 96.07% 85.14%
CHEMBL204 P00734 Thrombin 94.59% 96.01%
CHEMBL1902 P62942 FK506-binding protein 1A 93.73% 97.05%
CHEMBL215 P09917 Arachidonate 5-lipoxygenase 93.23% 92.68%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.33% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.95% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.42% 96.09%
CHEMBL1937 Q92769 Histone deacetylase 2 88.57% 94.75%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 88.49% 97.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.28% 86.33%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 87.41% 97.33%
CHEMBL1871 P10275 Androgen Receptor 87.03% 96.43%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 86.84% 91.11%
CHEMBL2996 Q05655 Protein kinase C delta 86.35% 97.79%
CHEMBL3820 P35557 Hexokinase type IV 85.85% 91.96%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.64% 94.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.56% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.77% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.21% 100.00%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 81.55% 100.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.10% 92.94%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.69% 93.04%
CHEMBL2581 P07339 Cathepsin D 80.13% 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 10505704
LOTUS LTS0144522
wikiData Q104910917