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(1R,2R,10R,11S,14R,15S,16S)-16-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.01,14.02,11.05,10]nonadeca-4,7-dien-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 1495b101-abed-4194-b37d-1b5aec72c95b
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1R,2R,10R,11S,14R,15S,16S)-16-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.01,14.02,11.05,10]nonadeca-4,7-dien-9-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C2(C3CCC4(C3(CCC5C4CC=C6C5(C(=O)C=CC6)C)C)O2)C)CO
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@]2([C@H]3CC[C@@]4([C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(C(=O)C=CC6)C)C)O2)C)CO
InChI InChI=1S/C28H36O5/c1-16-14-23(32-24(31)18(16)15-29)27(4)21-11-13-28(33-27)20-9-8-17-6-5-7-22(30)26(17,3)19(20)10-12-25(21,28)2/h5,7-8,19-21,23,29H,6,9-15H2,1-4H3/t19-,20+,21-,23+,25+,26-,27-,28+/m0/s1
InChI Key GRTVEVYXXCYKNH-LXSIAZRUSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C28H36O5
Molecular Weight 452.60 g/mol
Exact Mass 452.25627424 g/mol
Topological Polar Surface Area (TPSA) 72.80 Ų
XlogP 3.80
Atomic LogP (AlogP) 4.45
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,2R,10R,11S,14R,15S,16S)-16-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.01,14.02,11.05,10]nonadeca-4,7-dien-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 + 0.9693 96.93%
Caco-2 - 0.6414 64.14%
Blood Brain Barrier + 0.8500 85.00%
Human oral bioavailability + 0.5714 57.14%
Subcellular localzation Mitochondria 0.8673 86.73%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8187 81.87%
OATP1B3 inhibitior + 0.9334 93.34%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior + 0.9526 95.26%
P-glycoprotein inhibitior + 0.7202 72.02%
P-glycoprotein substrate - 0.5388 53.88%
CYP3A4 substrate + 0.7048 70.48%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9000 90.00%
CYP3A4 inhibition - 0.6563 65.63%
CYP2C9 inhibition - 0.9317 93.17%
CYP2C19 inhibition - 0.9563 95.63%
CYP2D6 inhibition - 0.9596 95.96%
CYP1A2 inhibition - 0.8679 86.79%
CYP2C8 inhibition + 0.5690 56.90%
CYP inhibitory promiscuity - 0.8988 89.88%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Danger 0.5471 54.71%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9593 95.93%
Skin irritation + 0.6397 63.97%
Skin corrosion - 0.9241 92.41%
Ames mutagenesis - 0.6170 61.70%
Human Ether-a-go-go-Related Gene inhibition - 0.3622 36.22%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.5624 56.24%
skin sensitisation - 0.9294 92.94%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity + 0.6028 60.28%
Acute Oral Toxicity (c) III 0.4697 46.97%
Estrogen receptor binding + 0.8768 87.68%
Androgen receptor binding + 0.7615 76.15%
Thyroid receptor binding + 0.6199 61.99%
Glucocorticoid receptor binding + 0.8700 87.00%
Aromatase binding + 0.7707 77.07%
PPAR gamma + 0.5870 58.70%
Honey bee toxicity - 0.8095 80.95%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9773 97.73%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.40% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.82% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.16% 97.25%
CHEMBL3192 Q9BY41 Histone deacetylase 8 89.91% 93.99%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.83% 97.09%
CHEMBL2581 P07339 Cathepsin D 89.68% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.51% 96.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.98% 100.00%
CHEMBL1937 Q92769 Histone deacetylase 2 86.73% 94.75%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.78% 86.33%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 85.55% 90.93%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.32% 99.23%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.32% 97.14%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 83.92% 82.69%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.86% 94.00%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 82.31% 93.03%
CHEMBL5103 Q969S8 Histone deacetylase 10 81.71% 90.08%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 80.15% 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 coagulans

Cross-Links

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PubChem 101936450
LOTUS LTS0189366
wikiData Q105016530