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(2R)-2-[(1R)-1-hydroxy-1-[(3R,8R,9S,10R,13R,14R,17S)-14-hydroxy-10,13-dimethyl-1-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,7,8,9,11,12,15,16,17-decahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-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 44c82826-9f23-49b2-9bf6-0a71bf93bd82
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-hydroxy-1-[(3R,8R,9S,10R,13R,14R,17S)-14-hydroxy-10,13-dimethyl-1-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,7,8,9,11,12,15,16,17-decahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C34H50O12/c1-16-11-25(46-29(41)19(16)14-35)33(4,42)23-8-10-34(43)21-6-5-17-12-18(44-30-28(40)27(39)26(38)22(15-36)45-30)13-24(37)32(17,3)20(21)7-9-31(23,34)2/h5,18,20-23,25-28,30,35-36,38-40,42-43H,6-15H2,1-4H3/t18-,20+,21-,22-,23+,25-,26-,27+,28-,30-,31-,32+,33-,34-/m1/s1
InChI Key QMXYKJHMLYEGKG-UVPMUZRKSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C34H50O12
Molecular Weight 650.80 g/mol
Exact Mass 650.33022703 g/mol
Topological Polar Surface Area (TPSA) 203.00 Ų
XlogP 0.00
Atomic LogP (AlogP) 0.42
H-Bond Acceptor 12
H-Bond Donor 7
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-hydroxy-1-[(3R,8R,9S,10R,13R,14R,17S)-14-hydroxy-10,13-dimethyl-1-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,7,8,9,11,12,15,16,17-decahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-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 + 0.7521 75.21%
Caco-2 - 0.8665 86.65%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.8375 83.75%
OATP2B1 inhibitior - 0.5805 58.05%
OATP1B1 inhibitior + 0.8508 85.08%
OATP1B3 inhibitior + 0.8381 83.81%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.5798 57.98%
BSEP inhibitior - 0.5881 58.81%
P-glycoprotein inhibitior + 0.7080 70.80%
P-glycoprotein substrate - 0.5079 50.79%
CYP3A4 substrate + 0.7353 73.53%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9041 90.41%
CYP3A4 inhibition - 0.8852 88.52%
CYP2C9 inhibition - 0.9245 92.45%
CYP2C19 inhibition - 0.9426 94.26%
CYP2D6 inhibition - 0.9538 95.38%
CYP1A2 inhibition - 0.9246 92.46%
CYP2C8 inhibition + 0.6343 63.43%
CYP inhibitory promiscuity - 0.9675 96.75%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5863 58.63%
Eye corrosion - 0.9904 99.04%
Eye irritation - 0.9266 92.66%
Skin irritation + 0.5512 55.12%
Skin corrosion - 0.9411 94.11%
Ames mutagenesis - 0.6454 64.54%
Human Ether-a-go-go-Related Gene inhibition + 0.7011 70.11%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.6750 67.50%
skin sensitisation - 0.9342 93.42%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity + 0.5070 50.70%
Acute Oral Toxicity (c) III 0.5383 53.83%
Estrogen receptor binding + 0.7602 76.02%
Androgen receptor binding + 0.7654 76.54%
Thyroid receptor binding - 0.6230 62.30%
Glucocorticoid receptor binding + 0.6850 68.50%
Aromatase binding + 0.6923 69.23%
PPAR gamma + 0.6497 64.97%
Honey bee toxicity - 0.7017 70.17%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.5400 54.00%
Fish aquatic toxicity + 0.9503 95.03%

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 98.59% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.84% 91.11%
CHEMBL1937 Q92769 Histone deacetylase 2 96.24% 94.75%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.09% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.55% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.66% 96.09%
CHEMBL5103 Q969S8 Histone deacetylase 10 90.64% 90.08%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.44% 86.33%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 90.43% 94.00%
CHEMBL2581 P07339 Cathepsin D 89.91% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.73% 85.14%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.09% 99.23%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 86.93% 93.04%
CHEMBL3359 P21462 Formyl peptide receptor 1 86.42% 93.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.58% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.33% 95.89%
CHEMBL3401 O75469 Pregnane X receptor 84.20% 94.73%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 82.55% 100.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.89% 97.14%
CHEMBL5255 O00206 Toll-like receptor 4 80.89% 92.50%
CHEMBL3524 P56524 Histone deacetylase 4 80.65% 92.97%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.38% 89.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.20% 92.62%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 80.08% 96.21%

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.
Physalis peruviana

Cross-Links

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PubChem 10580106
LOTUS LTS0021768
wikiData Q105224240