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(2R)-2-[(1S)-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]-5-(methoxymethyl)-4-methyl-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 70531e5a-75f2-43ea-92db-77f6bcae471d
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1S)-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]-5-(methoxymethyl)-4-methyl-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)COC
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)COC
InChI InChI=1S/C29H42O8/c1-15-10-22(37-26(34)18(15)14-36-4)17(13-30)20-8-7-19-16-11-25(33)29(35)9-5-6-23(31)28(29,3)21(16)12-24(32)27(19,20)2/h5-6,16-17,19-22,24-25,30,32-33,35H,7-14H2,1-4H3/t16-,17+,19-,20+,21-,22+,24+,25+,27-,28-,29-/m0/s1
InChI Key BOFMUGXANDFGGL-SOHIIPNCSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H42O8
Molecular Weight 518.60 g/mol
Exact Mass 518.28796829 g/mol
Topological Polar Surface Area (TPSA) 134.00 Ų
XlogP 1.40
Atomic LogP (AlogP) 1.93
H-Bond Acceptor 8
H-Bond Donor 4
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-2-[(1S)-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]-5-(methoxymethyl)-4-methyl-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 + 0.8699 86.99%
Caco-2 - 0.7555 75.55%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.7952 79.52%
OATP2B1 inhibitior - 0.7160 71.60%
OATP1B1 inhibitior + 0.8789 87.89%
OATP1B3 inhibitior + 0.9249 92.49%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7021 70.21%
BSEP inhibitior + 0.9776 97.76%
P-glycoprotein inhibitior + 0.5743 57.43%
P-glycoprotein substrate + 0.6663 66.63%
CYP3A4 substrate + 0.7275 72.75%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9046 90.46%
CYP3A4 inhibition - 0.7883 78.83%
CYP2C9 inhibition - 0.8997 89.97%
CYP2C19 inhibition - 0.8952 89.52%
CYP2D6 inhibition - 0.9540 95.40%
CYP1A2 inhibition - 0.8364 83.64%
CYP2C8 inhibition + 0.6541 65.41%
CYP inhibitory promiscuity - 0.9816 98.16%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6549 65.49%
Eye corrosion - 0.9904 99.04%
Eye irritation - 0.9556 95.56%
Skin irritation - 0.5604 56.04%
Skin corrosion - 0.9479 94.79%
Ames mutagenesis - 0.5467 54.67%
Human Ether-a-go-go-Related Gene inhibition + 0.6431 64.31%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.6182 61.82%
skin sensitisation - 0.9108 91.08%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity + 0.6046 60.46%
Acute Oral Toxicity (c) I 0.4971 49.71%
Estrogen receptor binding + 0.8098 80.98%
Androgen receptor binding + 0.7701 77.01%
Thyroid receptor binding + 0.5183 51.83%
Glucocorticoid receptor binding + 0.7851 78.51%
Aromatase binding + 0.6888 68.88%
PPAR gamma + 0.5499 54.99%
Honey bee toxicity - 0.6828 68.28%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.8979 89.79%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.47% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.12% 91.11%
CHEMBL2581 P07339 Cathepsin D 94.84% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.69% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.29% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.08% 95.56%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 89.61% 97.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.25% 86.33%
CHEMBL2996 Q05655 Protein kinase C delta 87.73% 97.79%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.24% 100.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.92% 95.89%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.77% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.39% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.21% 99.23%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 83.22% 96.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.17% 94.00%
CHEMBL226 P30542 Adenosine A1 receptor 83.06% 95.93%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.97% 99.17%
CHEMBL1871 P10275 Androgen Receptor 82.95% 96.43%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.42% 95.89%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.12% 93.04%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.03% 91.07%

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 163009432
LOTUS LTS0038284
wikiData Q104939203