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(2R)-2-[(1R)-1-[(5R,6R,8R,9R,10R,13S,14S,17R)-5,6-dihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-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 f72c8319-a3b6-4769-92bb-50b52d28e390
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1R)-1-[(5R,6R,8R,9R,10R,13S,14S,17R)-5,6-dihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(CO)C2CCC3C2(CCC4C3CC(C5(C4(C(=O)C=CC5)C)O)O)C)C
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@H](CO)[C@H]2CC[C@@H]3[C@@]2(CC[C@@H]4[C@@H]3C[C@H]([C@@]5([C@@]4(C(=O)C=CC5)C)O)O)C)C
InChI InChI=1S/C28H40O6/c1-15-12-22(34-25(32)16(15)2)18(14-29)20-8-7-19-17-13-24(31)28(33)10-5-6-23(30)27(28,4)21(17)9-11-26(19,20)3/h5-6,17-22,24,29,31,33H,7-14H2,1-4H3/t17-,18+,19+,20-,21-,22-,24-,26+,27+,28+/m1/s1
InChI Key RDDCFIGPZIZFRL-JKUPVXJISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H40O6
Molecular Weight 472.60 g/mol
Exact Mass 472.28248899 g/mol
Topological Polar Surface Area (TPSA) 104.00 Ų
XlogP 3.40
Atomic LogP (AlogP) 3.34
H-Bond Acceptor 6
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 (2R)-2-[(1R)-1-[(5R,6R,8R,9R,10R,13S,14S,17R)-5,6-dihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9102 91.02%
Caco-2 - 0.6804 68.04%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.8225 82.25%
OATP2B1 inhibitior - 0.8592 85.92%
OATP1B1 inhibitior + 0.8737 87.37%
OATP1B3 inhibitior + 0.9236 92.36%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5688 56.88%
BSEP inhibitior + 0.9359 93.59%
P-glycoprotein inhibitior - 0.4551 45.51%
P-glycoprotein substrate + 0.5729 57.29%
CYP3A4 substrate + 0.7343 73.43%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9074 90.74%
CYP3A4 inhibition - 0.7105 71.05%
CYP2C9 inhibition - 0.9203 92.03%
CYP2C19 inhibition - 0.9261 92.61%
CYP2D6 inhibition - 0.9609 96.09%
CYP1A2 inhibition - 0.8420 84.20%
CYP2C8 inhibition + 0.5135 51.35%
CYP inhibitory promiscuity - 0.9720 97.20%
UGT catelyzed + 1.0000 100.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6419 64.19%
Eye corrosion - 0.9930 99.30%
Eye irritation - 0.9621 96.21%
Skin irritation + 0.6729 67.29%
Skin corrosion - 0.9432 94.32%
Ames mutagenesis - 0.5822 58.22%
Human Ether-a-go-go-Related Gene inhibition + 0.6476 64.76%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.5484 54.84%
skin sensitisation - 0.9260 92.60%
Respiratory toxicity + 0.9000 90.00%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity - 0.6393 63.93%
Acute Oral Toxicity (c) III 0.4395 43.95%
Estrogen receptor binding + 0.8264 82.64%
Androgen receptor binding + 0.8047 80.47%
Thyroid receptor binding + 0.5479 54.79%
Glucocorticoid receptor binding + 0.7371 73.71%
Aromatase binding + 0.7262 72.62%
PPAR gamma + 0.5671 56.71%
Honey bee toxicity - 0.7758 77.58%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.9645 96.45%

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
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.89% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 93.21% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.57% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.37% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.82% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.87% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.27% 89.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 88.34% 93.04%
CHEMBL226 P30542 Adenosine A1 receptor 87.85% 95.93%
CHEMBL2581 P07339 Cathepsin D 86.50% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.36% 86.33%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.86% 97.14%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.64% 99.23%
CHEMBL204 P00734 Thrombin 84.22% 96.01%
CHEMBL1871 P10275 Androgen Receptor 84.07% 96.43%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.68% 85.14%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 82.54% 96.95%
CHEMBL221 P23219 Cyclooxygenase-1 81.76% 90.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.50% 95.89%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.27% 95.89%
CHEMBL2996 Q05655 Protein kinase C delta 81.00% 97.79%

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.
Datura metel

Cross-Links

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PubChem 162988723
LOTUS LTS0048551
wikiData Q105234151