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(2S)-2-[(1S)-1-[(5R,6R,8R,9R,10S,13S,14R,17S)-5-chloro-6,14,17-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-yl]-1-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 a7c5d269-2491-45b0-8ccc-5e9cf63e1574
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2S)-2-[(1S)-1-[(5R,6R,8R,9R,10S,13S,14R,17S)-5-chloro-6,14,17-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)(C2(CCC3(C2(CCC4C3CC(C5(C4(C(=O)C=CC5)C)Cl)O)C)O)O)O)C
SMILES (Isomeric) CC1=C(C(=O)O[C@@H](C1)[C@@](C)([C@@]2(CC[C@@]3([C@@]2(CC[C@@H]4[C@H]3C[C@H]([C@@]5([C@@]4(C(=O)C=CC5)C)Cl)O)C)O)O)O)C
InChI InChI=1S/C28H39ClO7/c1-15-13-21(36-22(32)16(15)2)25(5,33)28(35)12-11-27(34)18-14-20(31)26(29)9-6-7-19(30)24(26,4)17(18)8-10-23(27,28)3/h6-7,17-18,20-21,31,33-35H,8-14H2,1-5H3/t17-,18-,20-,21+,23+,24+,25+,26+,27-,28+/m1/s1
InChI Key JEJZNYLQNCIUEG-GAYBLMNASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H39ClO7
Molecular Weight 523.10 g/mol
Exact Mass 522.2384313 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP 2.00
Atomic LogP (AlogP) 2.96
H-Bond Acceptor 7
H-Bond Donor 4
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S)-2-[(1S)-1-[(5R,6R,8R,9R,10S,13S,14R,17S)-5-chloro-6,14,17-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-yl]-1-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 + 0.9285 92.85%
Caco-2 - 0.6870 68.70%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.6916 69.16%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8794 87.94%
OATP1B3 inhibitior + 0.8733 87.33%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior + 0.5179 51.79%
BSEP inhibitior + 0.8714 87.14%
P-glycoprotein inhibitior - 0.4614 46.14%
P-glycoprotein substrate + 0.5633 56.33%
CYP3A4 substrate + 0.7286 72.86%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9028 90.28%
CYP3A4 inhibition - 0.9220 92.20%
CYP2C9 inhibition - 0.8668 86.68%
CYP2C19 inhibition - 0.8667 86.67%
CYP2D6 inhibition - 0.9165 91.65%
CYP1A2 inhibition - 0.8421 84.21%
CYP2C8 inhibition + 0.5836 58.36%
CYP inhibitory promiscuity - 0.9692 96.92%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.8638 86.38%
Carcinogenicity (trinary) Non-required 0.5274 52.74%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9401 94.01%
Skin irritation + 0.5392 53.92%
Skin corrosion - 0.8957 89.57%
Ames mutagenesis - 0.6836 68.36%
Human Ether-a-go-go-Related Gene inhibition + 0.8253 82.53%
Micronuclear - 0.7900 79.00%
Hepatotoxicity + 0.6824 68.24%
skin sensitisation - 0.8324 83.24%
Respiratory toxicity + 0.8111 81.11%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity + 0.7729 77.29%
Acute Oral Toxicity (c) III 0.3762 37.62%
Estrogen receptor binding + 0.8118 81.18%
Androgen receptor binding + 0.7848 78.48%
Thyroid receptor binding + 0.6535 65.35%
Glucocorticoid receptor binding + 0.7583 75.83%
Aromatase binding + 0.7955 79.55%
PPAR gamma + 0.6479 64.79%
Honey bee toxicity - 0.8156 81.56%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6600 66.00%
Fish aquatic toxicity + 0.9918 99.18%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.94% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.52% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.83% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.37% 91.11%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 91.36% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.33% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.29% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.99% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.85% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.75% 95.89%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 86.67% 93.04%
CHEMBL1871 P10275 Androgen Receptor 86.44% 96.43%
CHEMBL218 P21554 Cannabinoid CB1 receptor 85.01% 96.61%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.28% 99.23%
CHEMBL3359 P21462 Formyl peptide receptor 1 83.43% 93.56%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 82.39% 93.03%
CHEMBL4040 P28482 MAP kinase ERK2 81.64% 83.82%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 81.33% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 81.25% 94.45%
CHEMBL2581 P07339 Cathepsin D 80.38% 98.95%

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 somnifera

Cross-Links

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PubChem 162970564
LOTUS LTS0114427
wikiData Q105126146