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(1S,2R,6S,7R,9R,11R,12R,15R,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-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 fa88df39-d438-4058-94ec-d6ab69ecccd0
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1S,2R,6S,7R,9R,11R,12R,15R,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-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)CCC6O)C)O5)C)O)C
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)CC[C@@H]6O)C)O5)C)O)C
InChI InChI=1S/C28H40O6/c1-14-12-22(33-24(31)15(14)2)27(5,32)19-7-6-17-16-13-23-28(34-23)21(30)9-8-20(29)26(28,4)18(16)10-11-25(17,19)3/h16-19,21-23,30,32H,6-13H2,1-5H3/t16-,17-,18+,19-,21+,22-,23-,25+,26+,27-,28-/m1/s1
InChI Key AHJAPIKROWNAGK-YUTHJNAWSA-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) 96.40 Ų
XlogP 3.10
Atomic LogP (AlogP) 3.72
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,2R,6S,7R,9R,11R,12R,15R,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-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 + 0.9576 95.76%
Caco-2 - 0.5891 58.91%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.6830 68.30%
OATP2B1 inhibitior - 0.7098 70.98%
OATP1B1 inhibitior + 0.8932 89.32%
OATP1B3 inhibitior + 0.9189 91.89%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.6374 63.74%
BSEP inhibitior + 0.6981 69.81%
P-glycoprotein inhibitior - 0.4941 49.41%
P-glycoprotein substrate - 0.5711 57.11%
CYP3A4 substrate + 0.7485 74.85%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8953 89.53%
CYP3A4 inhibition - 0.7609 76.09%
CYP2C9 inhibition - 0.8586 85.86%
CYP2C19 inhibition - 0.8921 89.21%
CYP2D6 inhibition - 0.9560 95.60%
CYP1A2 inhibition - 0.7538 75.38%
CYP2C8 inhibition + 0.5133 51.33%
CYP inhibitory promiscuity - 0.9760 97.60%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5461 54.61%
Eye corrosion - 0.9917 99.17%
Eye irritation - 0.9498 94.98%
Skin irritation + 0.5729 57.29%
Skin corrosion - 0.9051 90.51%
Ames mutagenesis - 0.6137 61.37%
Human Ether-a-go-go-Related Gene inhibition - 0.4390 43.90%
Micronuclear - 0.6900 69.00%
Hepatotoxicity + 0.5783 57.83%
skin sensitisation - 0.8195 81.95%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9250 92.50%
Nephrotoxicity + 0.5958 59.58%
Acute Oral Toxicity (c) I 0.4368 43.68%
Estrogen receptor binding + 0.7510 75.10%
Androgen receptor binding + 0.7860 78.60%
Thyroid receptor binding - 0.4883 48.83%
Glucocorticoid receptor binding + 0.7790 77.90%
Aromatase binding + 0.7817 78.17%
PPAR gamma + 0.6478 64.78%
Honey bee toxicity - 0.8216 82.16%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.6300 63.00%
Fish aquatic toxicity + 0.9780 97.80%

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 97.52% 85.14%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 92.78% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.62% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.60% 97.25%
CHEMBL204 P00734 Thrombin 89.83% 96.01%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.79% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.71% 97.09%
CHEMBL1871 P10275 Androgen Receptor 87.11% 96.43%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 87.00% 93.04%
CHEMBL1937 Q92769 Histone deacetylase 2 86.58% 94.75%
CHEMBL1902 P62942 FK506-binding protein 1A 85.49% 97.05%
CHEMBL3359 P21462 Formyl peptide receptor 1 84.39% 93.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.73% 86.33%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.58% 97.14%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 82.47% 82.69%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.02% 94.00%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 80.98% 97.33%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 80.81% 100.00%
CHEMBL2996 Q05655 Protein kinase C delta 80.20% 97.79%
CHEMBL5028 O14672 ADAM10 80.19% 97.50%
CHEMBL4302 P08183 P-glycoprotein 1 80.17% 92.98%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.02% 89.00%

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 163010459
LOTUS LTS0055984
wikiData Q105220951