(2R)-4,5-dimethyl-2-[(1S)-1-[(1S,2S,4S,5R,7S,9S,10S,11S,14R,15R,18S)-5,7,9-trihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadecan-15-yl]ethyl]-2,3-dihydropyran-6-one

Details

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Internal ID e74bc199-05e1-4b1e-b804-c1d96cfa1428
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-4,5-dimethyl-2-[(1S)-1-[(1S,2S,4S,5R,7S,9S,10S,11S,14R,15R,18S)-5,7,9-trihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadecan-15-yl]ethyl]-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3C5C(O5)C6(C4(C(CC(C6)O)O)C)O)C)C
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]3[C@H]5[C@H](O5)[C@@]6([C@@]4([C@H](C[C@@H](C6)O)O)C)O)C)C
InChI InChI=1S/C28H42O6/c1-13-10-20(33-25(31)14(13)2)15(3)17-6-7-18-22-19(8-9-26(17,18)4)27(5)21(30)11-16(29)12-28(27,32)24-23(22)34-24/h15-24,29-30,32H,6-12H2,1-5H3/t15-,16-,17+,18-,19-,20+,21-,22-,23-,24-,26+,27-,28-/m0/s1
InChI Key KKJFBZYVMWSSOY-DLMIMKPCSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H42O6
Molecular Weight 474.60 g/mol
Exact Mass 474.29813906 g/mol
Topological Polar Surface Area (TPSA) 99.50 Ų
XlogP 3.90
Atomic LogP (AlogP) 3.37
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-4,5-dimethyl-2-[(1S)-1-[(1S,2S,4S,5R,7S,9S,10S,11S,14R,15R,18S)-5,7,9-trihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadecan-15-yl]ethyl]-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 + 0.9224 92.24%
Caco-2 - 0.6613 66.13%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.5486 54.86%
OATP2B1 inhibitior - 0.5771 57.71%
OATP1B1 inhibitior + 0.8667 86.67%
OATP1B3 inhibitior + 0.9749 97.49%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.8444 84.44%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate + 0.5685 56.85%
CYP3A4 substrate + 0.7351 73.51%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8809 88.09%
CYP3A4 inhibition - 0.8582 85.82%
CYP2C9 inhibition - 0.8901 89.01%
CYP2C19 inhibition - 0.9046 90.46%
CYP2D6 inhibition - 0.9438 94.38%
CYP1A2 inhibition - 0.7077 70.77%
CYP2C8 inhibition - 0.6332 63.32%
CYP inhibitory promiscuity - 0.9480 94.80%
UGT catelyzed + 1.0000 100.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5507 55.07%
Eye corrosion - 0.9912 99.12%
Eye irritation - 0.9503 95.03%
Skin irritation + 0.5639 56.39%
Skin corrosion - 0.9113 91.13%
Ames mutagenesis - 0.5827 58.27%
Human Ether-a-go-go-Related Gene inhibition - 0.4440 44.40%
Micronuclear - 0.6700 67.00%
Hepatotoxicity + 0.6318 63.18%
skin sensitisation - 0.8067 80.67%
Respiratory toxicity + 0.8778 87.78%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity + 0.5904 59.04%
Acute Oral Toxicity (c) I 0.3791 37.91%
Estrogen receptor binding + 0.7226 72.26%
Androgen receptor binding + 0.7392 73.92%
Thyroid receptor binding + 0.5683 56.83%
Glucocorticoid receptor binding + 0.6290 62.90%
Aromatase binding + 0.6494 64.94%
PPAR gamma + 0.6794 67.94%
Honey bee toxicity - 0.7799 77.99%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity + 0.5400 54.00%
Fish aquatic toxicity + 0.9560 95.60%

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 93.36% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.66% 95.56%
CHEMBL299 P17252 Protein kinase C alpha 92.41% 98.03%
CHEMBL220 P22303 Acetylcholinesterase 90.49% 94.45%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.01% 99.23%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.66% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 89.46% 93.04%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.34% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 88.43% 90.17%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 87.40% 96.38%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.94% 97.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.65% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.45% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.77% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.36% 95.89%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 84.87% 91.11%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 84.27% 90.71%
CHEMBL1871 P10275 Androgen Receptor 82.37% 96.43%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.35% 93.56%
CHEMBL5103 Q969S8 Histone deacetylase 10 81.42% 90.08%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 81.22% 85.14%
CHEMBL2179 P04062 Beta-glucocerebrosidase 80.63% 85.31%
CHEMBL226 P30542 Adenosine A1 receptor 80.25% 95.93%

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 23266171
LOTUS LTS0251215
wikiData Q105142212