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[(1S,2R,6S,7S,9R,11R,12R,15S,16R)-15-[(1R)-1-[(2S)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-6-yl] acetate

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 9b32ad1b-d72c-4076-b5c0-b30046be7fb4
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name [(1S,2R,6S,7S,9R,11R,12R,15S,16R)-15-[(1R)-1-[(2S)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-6-yl] acetate
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)(C2CCC3(C2(CCC4C3CC5C6(C4(C(=O)C=CC6OC(=O)C)C)O5)C)O)O)C
SMILES (Isomeric) CC1=C(C(=O)O[C@@H](C1)[C@@](C)([C@H]2CC[C@@]3([C@@]2(CC[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=C[C@@H]6OC(=O)C)C)O5)C)O)O)C
InChI InChI=1S/C30H40O8/c1-15-13-23(37-25(33)16(15)2)28(6,34)20-10-12-29(35)19-14-24-30(38-24)22(36-17(3)31)8-7-21(32)27(30,5)18(19)9-11-26(20,29)4/h7-8,18-20,22-24,34-35H,9-14H2,1-6H3/t18-,19+,20-,22-,23-,24+,26+,27-,28+,29+,30+/m0/s1
InChI Key SEWNKESTDUPEMC-ZXYRYSQSSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C30H40O8
Molecular Weight 528.60 g/mol
Exact Mass 528.27231823 g/mol
Topological Polar Surface Area (TPSA) 123.00 Ų
XlogP 2.30
Atomic LogP (AlogP) 3.18
H-Bond Acceptor 8
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,2R,6S,7S,9R,11R,12R,15S,16R)-15-[(1R)-1-[(2S)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-6-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9565 95.65%
Caco-2 - 0.7274 72.74%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.5000 50.00%
Subcellular localzation Mitochondria 0.7060 70.60%
OATP2B1 inhibitior - 0.8618 86.18%
OATP1B1 inhibitior + 0.8425 84.25%
OATP1B3 inhibitior + 0.8847 88.47%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6874 68.74%
BSEP inhibitior + 0.8788 87.88%
P-glycoprotein inhibitior + 0.7315 73.15%
P-glycoprotein substrate + 0.5744 57.44%
CYP3A4 substrate + 0.7479 74.79%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9043 90.43%
CYP3A4 inhibition - 0.7519 75.19%
CYP2C9 inhibition - 0.8115 81.15%
CYP2C19 inhibition - 0.8689 86.89%
CYP2D6 inhibition - 0.9496 94.96%
CYP1A2 inhibition - 0.7258 72.58%
CYP2C8 inhibition + 0.6601 66.01%
CYP inhibitory promiscuity - 0.9590 95.90%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5853 58.53%
Eye corrosion - 0.9912 99.12%
Eye irritation - 0.9312 93.12%
Skin irritation + 0.5334 53.34%
Skin corrosion - 0.9146 91.46%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6972 69.72%
Micronuclear - 0.6400 64.00%
Hepatotoxicity - 0.5444 54.44%
skin sensitisation - 0.8396 83.96%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity + 0.7440 74.40%
Acute Oral Toxicity (c) I 0.4137 41.37%
Estrogen receptor binding + 0.8148 81.48%
Androgen receptor binding + 0.7684 76.84%
Thyroid receptor binding + 0.5628 56.28%
Glucocorticoid receptor binding + 0.7604 76.04%
Aromatase binding + 0.7989 79.89%
PPAR gamma + 0.6543 65.43%
Honey bee toxicity - 0.7340 73.40%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5900 59.00%
Fish aquatic toxicity + 0.9808 98.08%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.78% 85.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.18% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.92% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.20% 95.56%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 92.67% 93.04%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 91.28% 97.14%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 91.24% 82.69%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.04% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.86% 99.23%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 88.67% 91.07%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.64% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.49% 89.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.85% 96.09%
CHEMBL3359 P21462 Formyl peptide receptor 1 86.05% 93.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.73% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.63% 100.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.07% 94.00%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 82.46% 95.71%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 82.11% 94.62%
CHEMBL340 P08684 Cytochrome P450 3A4 82.04% 91.19%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 81.67% 100.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.45% 92.62%
CHEMBL5028 O14672 ADAM10 80.05% 97.50%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 80.05% 97.33%

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 163047876
LOTUS LTS0119604
wikiData Q105251573