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(2R)-2-[(1R)-2-hydroxy-1-[(5R,6R,8S,9S,10R,12R,13S,14S,17R)-5,6,12-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-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 f9bbdee4-3416-4592-989e-6250c78a0c45
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1R)-2-hydroxy-1-[(5R,6R,8S,9S,10R,12R,13S,14S,17R)-5,6,12-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(CO)C2CCC3C2(C(CC4C3CC(C5(C4(C(=O)C=CC5)C)O)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([C@@H](C[C@H]4[C@H]3C[C@H]([C@@]5([C@@]4(C(=O)C=CC5)C)O)O)O)C)C
InChI InChI=1S/C28H40O7/c1-14-10-21(35-25(33)15(14)2)17(13-29)19-8-7-18-16-11-24(32)28(34)9-5-6-22(30)27(28,4)20(16)12-23(31)26(18,19)3/h5-6,16-21,23-24,29,31-32,34H,7-13H2,1-4H3/t16-,17-,18-,19+,20-,21+,23+,24+,26-,27-,28-/m0/s1
InChI Key PXBJIGCBUIUIPR-OOHVVAOXSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H40O7
Molecular Weight 488.60 g/mol
Exact Mass 488.27740361 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP 2.10
Atomic LogP (AlogP) 2.31
H-Bond Acceptor 7
H-Bond Donor 4
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)-2-hydroxy-1-[(5R,6R,8S,9S,10R,12R,13S,14S,17R)-5,6,12-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-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 - 0.7234 72.34%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.8225 82.25%
OATP2B1 inhibitior - 0.7183 71.83%
OATP1B1 inhibitior + 0.8920 89.20%
OATP1B3 inhibitior + 0.9236 92.36%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5688 56.88%
BSEP inhibitior + 0.9131 91.31%
P-glycoprotein inhibitior - 0.4740 47.40%
P-glycoprotein substrate + 0.6264 62.64%
CYP3A4 substrate + 0.7013 70.13%
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 + 0.5530 55.30%
CYP inhibitory promiscuity - 0.9720 97.20%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6419 64.19%
Eye corrosion - 0.9930 99.30%
Eye irritation - 0.9597 95.97%
Skin irritation + 0.6729 67.29%
Skin corrosion - 0.9432 94.32%
Ames mutagenesis - 0.5183 51.83%
Human Ether-a-go-go-Related Gene inhibition + 0.6795 67.95%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.5859 58.59%
skin sensitisation - 0.9260 92.60%
Respiratory toxicity + 0.7889 78.89%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.5914 59.14%
Acute Oral Toxicity (c) III 0.4395 43.95%
Estrogen receptor binding + 0.8533 85.33%
Androgen receptor binding + 0.7677 76.77%
Thyroid receptor binding + 0.5442 54.42%
Glucocorticoid receptor binding + 0.7375 73.75%
Aromatase binding + 0.7043 70.43%
PPAR gamma + 0.5734 57.34%
Honey bee toxicity - 0.7717 77.17%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5600 56.00%
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 93.74% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.71% 91.11%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.20% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.01% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.91% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.97% 85.14%
CHEMBL226 P30542 Adenosine A1 receptor 89.57% 95.93%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.99% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.63% 89.00%
CHEMBL2581 P07339 Cathepsin D 88.55% 98.95%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 87.27% 93.04%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.50% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.63% 86.33%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.25% 97.14%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 82.05% 86.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.95% 95.89%
CHEMBL1871 P10275 Androgen Receptor 80.26% 96.43%

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 163195472
LOTUS LTS0163476
wikiData Q105216089