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(1S,2R,5S,6S,7R,9R,11S,12S,14S,15R,16S)-15-[(1R)-1-[(2R,4S,5R)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-6,14-dihydroxy-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 8e15edb9-4267-4945-a3c2-a7a6f4d24487
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,14S,15R,16S)-15-[(1R)-1-[(2R,4S,5R)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-6,14-dihydroxy-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)(C2C(CC3C2(CCC4C3CC5C6(C4(C(=O)CC(C6O)OC)C)O5)C)O)O
SMILES (Isomeric) C[C@H]1C[C@@H](OC(=O)[C@@H]1C)[C@@](C)([C@H]2[C@H](C[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)O
InChI InChI=1S/C29H44O8/c1-13-9-21(36-25(33)14(13)2)28(5,34)23-18(30)11-17-15-10-22-29(37-22)24(32)19(35-6)12-20(31)27(29,4)16(15)7-8-26(17,23)3/h13-19,21-24,30,32,34H,7-12H2,1-6H3/t13-,14+,15+,16-,17-,18-,19-,21+,22+,23-,24-,26-,27-,28-,29-/m0/s1
InChI Key UIRURUXXWSKXCE-IGMURQQCSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H44O8
Molecular Weight 520.70 g/mol
Exact Mass 520.30361836 g/mol
Topological Polar Surface Area (TPSA) 126.00 Ų
XlogP 2.60
Atomic LogP (AlogP) 2.25
H-Bond Acceptor 8
H-Bond Donor 3
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,14S,15R,16S)-15-[(1R)-1-[(2R,4S,5R)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-6,14-dihydroxy-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 + 0.8006 80.06%
Caco-2 - 0.7692 76.92%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability + 0.5286 52.86%
Subcellular localzation Mitochondria 0.5766 57.66%
OATP2B1 inhibitior - 0.7172 71.72%
OATP1B1 inhibitior + 0.8638 86.38%
OATP1B3 inhibitior + 0.9118 91.18%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7571 75.71%
BSEP inhibitior - 0.6908 69.08%
P-glycoprotein inhibitior - 0.4510 45.10%
P-glycoprotein substrate + 0.5789 57.89%
CYP3A4 substrate + 0.7464 74.64%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8451 84.51%
CYP3A4 inhibition - 0.7504 75.04%
CYP2C9 inhibition - 0.8275 82.75%
CYP2C19 inhibition - 0.8580 85.80%
CYP2D6 inhibition - 0.9444 94.44%
CYP1A2 inhibition - 0.7751 77.51%
CYP2C8 inhibition + 0.5256 52.56%
CYP inhibitory promiscuity - 0.9807 98.07%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6657 66.57%
Eye corrosion - 0.9894 98.94%
Eye irritation - 0.9425 94.25%
Skin irritation - 0.6117 61.17%
Skin corrosion - 0.9019 90.19%
Ames mutagenesis - 0.6054 60.54%
Human Ether-a-go-go-Related Gene inhibition - 0.4876 48.76%
Micronuclear - 0.7000 70.00%
Hepatotoxicity + 0.6533 65.33%
skin sensitisation - 0.8889 88.89%
Respiratory toxicity + 0.8333 83.33%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.8625 86.25%
Nephrotoxicity + 0.5647 56.47%
Acute Oral Toxicity (c) I 0.3537 35.37%
Estrogen receptor binding + 0.6740 67.40%
Androgen receptor binding + 0.7658 76.58%
Thyroid receptor binding - 0.6057 60.57%
Glucocorticoid receptor binding + 0.6692 66.92%
Aromatase binding + 0.7332 73.32%
PPAR gamma + 0.6059 60.59%
Honey bee toxicity - 0.6055 60.55%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.6400 64.00%
Fish aquatic toxicity + 0.8694 86.94%

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 98.15% 85.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.69% 97.25%
CHEMBL204 P00734 Thrombin 95.50% 96.01%
CHEMBL1902 P62942 FK506-binding protein 1A 93.34% 97.05%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.00% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.40% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.20% 96.09%
CHEMBL2996 Q05655 Protein kinase C delta 91.07% 97.79%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 88.47% 97.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.38% 86.33%
CHEMBL1871 P10275 Androgen Receptor 87.29% 96.43%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.83% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.65% 99.23%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.38% 93.04%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 85.16% 97.33%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 83.98% 100.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.54% 94.00%
CHEMBL3820 P35557 Hexokinase type IV 82.77% 91.96%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.90% 92.94%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 81.54% 91.03%
CHEMBL2581 P07339 Cathepsin D 81.38% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.19% 100.00%
CHEMBL1937 Q92769 Histone deacetylase 2 80.75% 94.75%

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.
Physalis philadelphica

Cross-Links

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PubChem 102330251
LOTUS LTS0218115
wikiData Q105273550