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(1R,2R,6S,7R,9R,11R,12S,15S,16S)-6-hydroxy-15-[(1R)-1-hydroxy-1-[(2S)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-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 6d4aab77-5eb3-4dd9-b5aa-8216cb946330
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1R,2R,6S,7R,9R,11R,12S,15S,16S)-6-hydroxy-15-[(1R)-1-hydroxy-1-[(2S)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)O)CO
SMILES (Isomeric) CC1=C(C(=O)O[C@@H](C1)[C@@](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[C@@H]6O)C)O5)C)O)CO
InChI InChI=1S/C28H38O7/c1-14-11-22(34-24(32)16(14)13-29)27(4,33)19-6-5-17-15-12-23-28(35-23)21(31)8-7-20(30)26(28,3)18(15)9-10-25(17,19)2/h7-8,15,17-19,21-23,29,31,33H,5-6,9-13H2,1-4H3/t15-,17+,18-,19+,21+,22+,23-,25+,26+,27-,28-/m1/s1
InChI Key HBSNZLRSNURUSG-WWTOYDKJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H38O7
Molecular Weight 486.60 g/mol
Exact Mass 486.26175355 g/mol
Topological Polar Surface Area (TPSA) 117.00 Ų
XlogP 2.40
Atomic LogP (AlogP) 2.47
H-Bond Acceptor 7
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,2R,6S,7R,9R,11R,12S,15S,16S)-6-hydroxy-15-[(1R)-1-hydroxy-1-[(2S)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-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 + 0.9227 92.27%
Caco-2 - 0.6892 68.92%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability + 0.5143 51.43%
Subcellular localzation Mitochondria 0.7888 78.88%
OATP2B1 inhibitior - 0.7128 71.28%
OATP1B1 inhibitior + 0.8480 84.80%
OATP1B3 inhibitior + 0.9352 93.52%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.5796 57.96%
BSEP inhibitior + 0.8435 84.35%
P-glycoprotein inhibitior - 0.4493 44.93%
P-glycoprotein substrate + 0.5481 54.81%
CYP3A4 substrate + 0.7474 74.74%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8961 89.61%
CYP3A4 inhibition - 0.8268 82.68%
CYP2C9 inhibition - 0.8386 83.86%
CYP2C19 inhibition - 0.9231 92.31%
CYP2D6 inhibition - 0.9536 95.36%
CYP1A2 inhibition - 0.8179 81.79%
CYP2C8 inhibition + 0.5054 50.54%
CYP inhibitory promiscuity - 0.9386 93.86%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5967 59.67%
Eye corrosion - 0.9903 99.03%
Eye irritation - 0.9584 95.84%
Skin irritation + 0.5112 51.12%
Skin corrosion - 0.9355 93.55%
Ames mutagenesis - 0.5448 54.48%
Human Ether-a-go-go-Related Gene inhibition - 0.3709 37.09%
Micronuclear - 0.7400 74.00%
Hepatotoxicity + 0.5250 52.50%
skin sensitisation - 0.8958 89.58%
Respiratory toxicity + 0.8667 86.67%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity + 0.5074 50.74%
Acute Oral Toxicity (c) I 0.5355 53.55%
Estrogen receptor binding + 0.7567 75.67%
Androgen receptor binding + 0.7786 77.86%
Thyroid receptor binding + 0.5357 53.57%
Glucocorticoid receptor binding + 0.8096 80.96%
Aromatase binding + 0.7717 77.17%
PPAR gamma + 0.5785 57.85%
Honey bee toxicity - 0.7858 78.58%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity + 0.9721 97.21%

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
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.18% 95.56%
CHEMBL2581 P07339 Cathepsin D 92.81% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.71% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.49% 97.09%
CHEMBL2996 Q05655 Protein kinase C delta 91.00% 97.79%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 88.37% 97.14%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.38% 85.14%
CHEMBL1871 P10275 Androgen Receptor 86.78% 96.43%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.22% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 85.98% 82.69%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.65% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 83.85% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.46% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 83.05% 94.73%
CHEMBL1937 Q92769 Histone deacetylase 2 81.68% 94.75%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.58% 99.23%
CHEMBL1902 P62942 FK506-binding protein 1A 81.05% 97.05%
CHEMBL5103 Q969S8 Histone deacetylase 10 80.93% 90.08%
CHEMBL5028 O14672 ADAM10 80.79% 97.50%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.65% 95.89%

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 163188002
LOTUS LTS0243587
wikiData Q105025469