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(2R)-2-[(1R)-1-[(8S,9S,10R,13S,14S,17R)-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-hydroxyethyl]-4-methyl-5-[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-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 9b700e6d-0da9-4146-9c2e-1dff0be39acb
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1R)-1-[(8S,9S,10R,13S,14S,17R)-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-hydroxyethyl]-4-methyl-5-[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(CO)C2CCC3C2(CCC4C3CC=C5C4(C(=O)C=CC5)C)C)COC6C(C(C(C(O6)CO)O)O)O
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]3CC=C5[C@@]4(C(=O)C=CC5)C)C)COC6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
InChI InChI=1S/C34H48O10/c1-17-13-25(43-31(41)21(17)16-42-32-30(40)29(39)28(38)26(15-36)44-32)20(14-35)23-10-9-22-19-8-7-18-5-4-6-27(37)34(18,3)24(19)11-12-33(22,23)2/h4,6-7,19-20,22-26,28-30,32,35-36,38-40H,5,8-16H2,1-3H3/t19-,20-,22-,23+,24-,25+,26+,28+,29-,30+,32?,33-,34-/m0/s1
InChI Key GHOHERGSBUWNTN-VQWQZRNGSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C34H48O10
Molecular Weight 616.70 g/mol
Exact Mass 616.32474772 g/mol
Topological Polar Surface Area (TPSA) 163.00 Ų
XlogP 2.20
Atomic LogP (AlogP) 1.97
H-Bond Acceptor 10
H-Bond Donor 5
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-2-[(1R)-1-[(8S,9S,10R,13S,14S,17R)-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-hydroxyethyl]-4-methyl-5-[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-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 + 0.7135 71.35%
Caco-2 - 0.8697 86.97%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.8629 86.29%
OATP2B1 inhibitior - 0.5773 57.73%
OATP1B1 inhibitior + 0.8499 84.99%
OATP1B3 inhibitior + 0.7884 78.84%
MATE1 inhibitior - 0.9812 98.12%
OCT2 inhibitior - 0.5298 52.98%
BSEP inhibitior + 0.9070 90.70%
P-glycoprotein inhibitior + 0.6938 69.38%
P-glycoprotein substrate + 0.5842 58.42%
CYP3A4 substrate + 0.7549 75.49%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8984 89.84%
CYP3A4 inhibition - 0.9295 92.95%
CYP2C9 inhibition - 0.9215 92.15%
CYP2C19 inhibition - 0.9385 93.85%
CYP2D6 inhibition - 0.9550 95.50%
CYP1A2 inhibition - 0.8971 89.71%
CYP2C8 inhibition + 0.6903 69.03%
CYP inhibitory promiscuity - 0.9438 94.38%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6009 60.09%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9371 93.71%
Skin irritation + 0.4910 49.10%
Skin corrosion - 0.9419 94.19%
Ames mutagenesis - 0.7144 71.44%
Human Ether-a-go-go-Related Gene inhibition + 0.8096 80.96%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.6913 69.13%
skin sensitisation - 0.9349 93.49%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity - 0.6404 64.04%
Acute Oral Toxicity (c) III 0.5730 57.30%
Estrogen receptor binding + 0.7841 78.41%
Androgen receptor binding + 0.7538 75.38%
Thyroid receptor binding - 0.6250 62.50%
Glucocorticoid receptor binding + 0.6677 66.77%
Aromatase binding + 0.6031 60.31%
PPAR gamma + 0.5655 56.55%
Honey bee toxicity - 0.6635 66.35%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5350 53.50%
Fish aquatic toxicity + 0.9668 96.68%

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 96.33% 96.09%
CHEMBL2581 P07339 Cathepsin D 95.03% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.61% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.49% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.67% 95.56%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 91.44% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 90.19% 94.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.53% 100.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 88.39% 97.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.22% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.79% 89.00%
CHEMBL1937 Q92769 Histone deacetylase 2 87.45% 94.75%
CHEMBL3401 O75469 Pregnane X receptor 87.26% 94.73%
CHEMBL3714130 P46095 G-protein coupled receptor 6 85.68% 97.36%
CHEMBL5103 Q969S8 Histone deacetylase 10 84.20% 90.08%
CHEMBL226 P30542 Adenosine A1 receptor 83.58% 95.93%
CHEMBL204 P00734 Thrombin 82.97% 96.01%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.52% 99.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.15% 99.23%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.73% 93.04%
CHEMBL3359 P21462 Formyl peptide receptor 1 81.47% 93.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.82% 95.89%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.60% 97.25%

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 163025412
LOTUS LTS0049892
wikiData Q105008638