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(2R)-2-[(1R)-1-[(3R,8R,9S,10R,13R,17S)-10,13-dimethyl-1-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,7,8,9,11,12,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-5-(hydroxymethyl)-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 d8e62280-4f8a-4a0f-8939-2fc78ea64f0f
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
IUPAC Name (2R)-2-[(1R)-1-[(3R,8R,9S,10R,13R,17S)-10,13-dimethyl-1-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,7,8,9,11,12,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)(C2CC=C3C2(CCC4C3CC=C5C4(C(=O)CC(C5)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)CO
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@H]2CC=C3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(C(=O)C[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)O)CO
InChI InChI=1S/C34H48O11/c1-16-11-26(45-30(41)20(16)14-35)34(4,42)24-8-7-21-19-6-5-17-12-18(43-31-29(40)28(39)27(38)23(15-36)44-31)13-25(37)33(17,3)22(19)9-10-32(21,24)2/h5,7,18-19,22-24,26-29,31,35-36,38-40,42H,6,8-15H2,1-4H3/t18-,19+,22+,23-,24+,26-,27-,28+,29-,31-,32+,33+,34-/m1/s1
InChI Key HRLAOGLDPYVVAD-YUXWAEGMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C34H48O11
Molecular Weight 632.70 g/mol
Exact Mass 632.31966234 g/mol
Topological Polar Surface Area (TPSA) 183.00 Ų
XlogP 0.70
Atomic LogP (AlogP) 1.22
H-Bond Acceptor 11
H-Bond Donor 6
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-2-[(1R)-1-[(3R,8R,9S,10R,13R,17S)-10,13-dimethyl-1-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,7,8,9,11,12,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-5-(hydroxymethyl)-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 + 0.7135 71.35%
Caco-2 - 0.8655 86.55%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.8629 86.29%
OATP2B1 inhibitior - 0.7193 71.93%
OATP1B1 inhibitior + 0.8528 85.28%
OATP1B3 inhibitior + 0.7884 78.84%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.5298 52.98%
BSEP inhibitior - 0.4587 45.87%
P-glycoprotein inhibitior + 0.7017 70.17%
P-glycoprotein substrate - 0.5325 53.25%
CYP3A4 substrate + 0.7374 73.74%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9041 90.41%
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 + 0.6737 67.37%
CYP inhibitory promiscuity - 0.9438 94.38%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6009 60.09%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9337 93.37%
Skin irritation + 0.4910 49.10%
Skin corrosion - 0.9419 94.19%
Ames mutagenesis - 0.7124 71.24%
Human Ether-a-go-go-Related Gene inhibition + 0.6561 65.61%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.6625 66.25%
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 + 0.5000 50.00%
Acute Oral Toxicity (c) III 0.5730 57.30%
Estrogen receptor binding + 0.7864 78.64%
Androgen receptor binding + 0.7414 74.14%
Thyroid receptor binding - 0.5991 59.91%
Glucocorticoid receptor binding + 0.6963 69.63%
Aromatase binding + 0.6623 66.23%
PPAR gamma + 0.6555 65.55%
Honey bee toxicity - 0.6874 68.74%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.5700 57.00%
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
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.00% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.27% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.37% 97.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.06% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.94% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.47% 96.09%
CHEMBL1937 Q92769 Histone deacetylase 2 90.11% 94.75%
CHEMBL2581 P07339 Cathepsin D 89.14% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 88.66% 94.00%
CHEMBL3401 O75469 Pregnane X receptor 88.01% 94.73%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.35% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.53% 86.33%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 86.33% 86.92%
CHEMBL5103 Q969S8 Histone deacetylase 10 85.32% 90.08%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.83% 100.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 83.87% 93.56%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 82.56% 100.00%
CHEMBL218 P21554 Cannabinoid CB1 receptor 82.45% 96.61%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.52% 100.00%
CHEMBL2996 Q05655 Protein kinase C delta 81.25% 97.79%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.79% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.59% 97.14%
CHEMBL5255 O00206 Toll-like receptor 4 80.42% 92.50%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.30% 92.62%

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 coagulans

Cross-Links

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PubChem 10794094
LOTUS LTS0226187
wikiData Q104888750