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(2R)-2-[(1S)-1-[(5R,6R,8S,9S,10R,13S,14S,17R)-5,6-dihydroxy-10,13-dimethyl-1-oxo-3,4,6,7,8,9,11,12,14,15,16,17-dodecahydro-2H-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 e4fe55c3-0f9b-4b12-90ed-c8ce14289b2d
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1S)-1-[(5R,6R,8S,9S,10R,13S,14S,17R)-5,6-dihydroxy-10,13-dimethyl-1-oxo-3,4,6,7,8,9,11,12,14,15,16,17-dodecahydro-2H-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)CCC5)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)CCC5)C)O)O)C)C
InChI InChI=1S/C28H42O6/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/h17-22,24,29,31,33H,5-14H2,1-4H3/t17-,18+,19-,20+,21-,22+,24+,26-,27-,28-/m0/s1
InChI Key WJIFGCPZQNCQCO-HYIBSZJVSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C28H42O6
Molecular Weight 474.60 g/mol
Exact Mass 474.29813906 g/mol
Topological Polar Surface Area (TPSA) 104.00 Ų
XlogP 3.30
Atomic LogP (AlogP) 3.56
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-[(1S)-1-[(5R,6R,8S,9S,10R,13S,14S,17R)-5,6-dihydroxy-10,13-dimethyl-1-oxo-3,4,6,7,8,9,11,12,14,15,16,17-dodecahydro-2H-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 - 0.6677 66.77%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.8225 82.25%
OATP2B1 inhibitior - 0.5685 56.85%
OATP1B1 inhibitior + 0.8648 86.48%
OATP1B3 inhibitior + 0.9236 92.36%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5688 56.88%
BSEP inhibitior + 0.8886 88.86%
P-glycoprotein inhibitior - 0.5378 53.78%
P-glycoprotein substrate - 0.5415 54.15%
CYP3A4 substrate + 0.7250 72.50%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9056 90.56%
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 + 0.4766 47.66%
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 - 0.9444 94.44%
Skin irritation + 0.6729 67.29%
Skin corrosion - 0.9432 94.32%
Ames mutagenesis - 0.6232 62.32%
Human Ether-a-go-go-Related Gene inhibition - 0.4746 47.46%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.6163 61.63%
skin sensitisation - 0.9260 92.60%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity - 0.6787 67.87%
Acute Oral Toxicity (c) III 0.4395 43.95%
Estrogen receptor binding + 0.7967 79.67%
Androgen receptor binding + 0.8017 80.17%
Thyroid receptor binding - 0.5260 52.60%
Glucocorticoid receptor binding + 0.7404 74.04%
Aromatase binding + 0.7146 71.46%
PPAR gamma + 0.5466 54.66%
Honey bee toxicity - 0.7998 79.98%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5200 52.00%
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
CHEMBL204 P00734 Thrombin 96.27% 96.01%
CHEMBL4040 P28482 MAP kinase ERK2 93.88% 83.82%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.14% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.47% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.21% 97.09%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 91.65% 93.04%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.72% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.30% 99.23%
CHEMBL299 P17252 Protein kinase C alpha 87.85% 98.03%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.04% 96.09%
CHEMBL226 P30542 Adenosine A1 receptor 86.04% 95.93%
CHEMBL2996 Q05655 Protein kinase C delta 85.71% 97.79%
CHEMBL2581 P07339 Cathepsin D 85.32% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.03% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 84.52% 91.11%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 83.43% 96.38%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.37% 94.00%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 82.14% 93.03%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.70% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.46% 94.45%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 80.10% 98.75%

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.
Datura metel

Cross-Links

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PubChem 163189465
LOTUS LTS0051622
wikiData Q105306800