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(2R)-2-[(1S)-1-[(1S,2S,3S,6S,7R,9R,11S,12S,15R,16S)-3,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-15-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 8659f567-540c-42d9-8d9a-b5a2f6b50a90
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1S)-1-[(1S,2S,3S,6S,7R,9R,11S,12S,15R,16S)-3,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-15-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(C=CC6O)O)C)O5)C)CO
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@H](C=C[C@@H]6O)O)C)O5)C)CO
InChI InChI=1S/C28H40O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-24,29-31H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,22-,23-,24+,26+,27-,28+/m0/s1
InChI Key YCGBUPXEBUFYFV-IPYPROHWSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H40O6
Molecular Weight 472.60 g/mol
Exact Mass 472.28248899 g/mol
Topological Polar Surface Area (TPSA) 99.50 Ų
XlogP 3.80
Atomic LogP (AlogP) 3.14
H-Bond Acceptor 6
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 (2R)-2-[(1S)-1-[(1S,2S,3S,6S,7R,9R,11S,12S,15R,16S)-3,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-15-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 + 0.9182 91.82%
Caco-2 - 0.7116 71.16%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability + 0.6714 67.14%
Subcellular localzation Mitochondria 0.7245 72.45%
OATP2B1 inhibitior - 0.7145 71.45%
OATP1B1 inhibitior + 0.8136 81.36%
OATP1B3 inhibitior + 0.9645 96.45%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior + 0.9172 91.72%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate + 0.5749 57.49%
CYP3A4 substrate + 0.7276 72.76%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8702 87.02%
CYP3A4 inhibition - 0.9239 92.39%
CYP2C9 inhibition - 0.8890 88.90%
CYP2C19 inhibition - 0.9203 92.03%
CYP2D6 inhibition - 0.9459 94.59%
CYP1A2 inhibition - 0.7440 74.40%
CYP2C8 inhibition + 0.4464 44.64%
CYP inhibitory promiscuity - 0.9135 91.35%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5665 56.65%
Eye corrosion - 0.9904 99.04%
Eye irritation - 0.9637 96.37%
Skin irritation + 0.5269 52.69%
Skin corrosion - 0.9381 93.81%
Ames mutagenesis - 0.5348 53.48%
Human Ether-a-go-go-Related Gene inhibition + 0.6880 68.80%
Micronuclear - 0.7300 73.00%
Hepatotoxicity + 0.5344 53.44%
skin sensitisation - 0.8691 86.91%
Respiratory toxicity + 0.9000 90.00%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity - 0.5889 58.89%
Acute Oral Toxicity (c) I 0.4993 49.93%
Estrogen receptor binding + 0.7956 79.56%
Androgen receptor binding + 0.7433 74.33%
Thyroid receptor binding + 0.5537 55.37%
Glucocorticoid receptor binding + 0.7857 78.57%
Aromatase binding + 0.7161 71.61%
PPAR gamma + 0.5747 57.47%
Honey bee toxicity - 0.7503 75.03%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9533 95.33%

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 94.82% 95.56%
CHEMBL2581 P07339 Cathepsin D 94.52% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.09% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.70% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.36% 91.11%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.98% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.77% 99.23%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 85.62% 82.69%
CHEMBL5103 Q969S8 Histone deacetylase 10 85.55% 90.08%
CHEMBL2996 Q05655 Protein kinase C delta 85.15% 97.79%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.37% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.15% 100.00%
CHEMBL221 P23219 Cyclooxygenase-1 83.48% 90.17%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.56% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.97% 86.33%
CHEMBL5028 O14672 ADAM10 81.62% 97.50%
CHEMBL1871 P10275 Androgen Receptor 81.01% 96.43%
CHEMBL1937 Q92769 Histone deacetylase 2 80.94% 94.75%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.63% 95.89%
CHEMBL3004 P33527 Multidrug resistance-associated protein 1 80.51% 96.37%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.04% 94.45%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.02% 93.04%

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 162897405
LOTUS LTS0234175
wikiData Q105346243