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(1S,2R,5S,6S,7R,9R,11S,12S,15R,16S)-5,6-dihydroxy-2,16-dimethyl-15-[(1S)-1-[(2R)-4-methyl-6-oxo-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-2-yl]ethyl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-3-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 708324c7-f640-4594-ba9a-d8138c6da723
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1S,2R,5S,6S,7R,9R,11S,12S,15R,16S)-5,6-dihydroxy-2,16-dimethyl-15-[(1S)-1-[(2R)-4-methyl-6-oxo-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-2-yl]ethyl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-3-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)CC(C6O)O)C)O5)C)COC7C(C(C(C(O7)CO)O)O)O
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C[C@@H]([C@@H]6O)O)C)O5)C)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
InChI InChI=1S/C34H50O12/c1-14-9-22(44-30(42)17(14)13-43-31-28(40)27(39)26(38)23(12-35)45-31)15(2)18-5-6-19-16-10-25-34(46-25)29(41)21(36)11-24(37)33(34,4)20(16)7-8-32(18,19)3/h15-16,18-23,25-29,31,35-36,38-41H,5-13H2,1-4H3/t15-,16-,18+,19-,20-,21-,22+,23+,25+,26+,27-,28+,29-,31+,32+,33-,34-/m0/s1
InChI Key URTVJNWIDYWJDO-FFFLRIOSSA-N
Popularity 0 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) 196.00 Ų
XlogP 0.70
Atomic LogP (AlogP) 0.37
H-Bond Acceptor 12
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 (1S,2R,5S,6S,7R,9R,11S,12S,15R,16S)-5,6-dihydroxy-2,16-dimethyl-15-[(1S)-1-[(2R)-4-methyl-6-oxo-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-2-yl]ethyl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-3-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6962 69.62%
Caco-2 - 0.8795 87.95%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7318 73.18%
OATP2B1 inhibitior - 0.5788 57.88%
OATP1B1 inhibitior + 0.8300 83.00%
OATP1B3 inhibitior + 0.9250 92.50%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.6048 60.48%
BSEP inhibitior - 0.4756 47.56%
P-glycoprotein inhibitior + 0.6763 67.63%
P-glycoprotein substrate + 0.5573 55.73%
CYP3A4 substrate + 0.7446 74.46%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8911 89.11%
CYP3A4 inhibition - 0.8643 86.43%
CYP2C9 inhibition - 0.7869 78.69%
CYP2C19 inhibition - 0.8852 88.52%
CYP2D6 inhibition - 0.9409 94.09%
CYP1A2 inhibition - 0.8796 87.96%
CYP2C8 inhibition + 0.6200 62.00%
CYP inhibitory promiscuity - 0.9644 96.44%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6787 67.87%
Eye corrosion - 0.9886 98.86%
Eye irritation - 0.9305 93.05%
Skin irritation - 0.5647 56.47%
Skin corrosion - 0.9373 93.73%
Ames mutagenesis - 0.6332 63.32%
Human Ether-a-go-go-Related Gene inhibition + 0.7266 72.66%
Micronuclear - 0.7000 70.00%
Hepatotoxicity - 0.6356 63.56%
skin sensitisation - 0.9010 90.10%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity + 0.5721 57.21%
Acute Oral Toxicity (c) I 0.6982 69.82%
Estrogen receptor binding + 0.7305 73.05%
Androgen receptor binding + 0.7681 76.81%
Thyroid receptor binding - 0.6558 65.58%
Glucocorticoid receptor binding + 0.6226 62.26%
Aromatase binding + 0.6858 68.58%
PPAR gamma + 0.5886 58.86%
Honey bee toxicity - 0.6694 66.94%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9509 95.09%

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 96.60% 96.01%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.78% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.84% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.76% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.37% 91.11%
CHEMBL1937 Q92769 Histone deacetylase 2 92.93% 94.75%
CHEMBL2581 P07339 Cathepsin D 92.77% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.21% 95.56%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 91.11% 95.89%
CHEMBL5103 Q969S8 Histone deacetylase 10 90.64% 90.08%
CHEMBL2996 Q05655 Protein kinase C delta 90.49% 97.79%
CHEMBL220 P22303 Acetylcholinesterase 89.54% 94.45%
CHEMBL3837 P07711 Cathepsin L 87.75% 96.61%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.23% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.92% 86.33%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 86.40% 96.21%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.31% 94.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 84.77% 93.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.69% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 83.88% 93.04%
CHEMBL3401 O75469 Pregnane X receptor 83.77% 94.73%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.02% 97.14%

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 163194503
LOTUS LTS0215193
wikiData Q105278037