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9-[1-(4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-6,9-dihydroxy-9a,11b-dimethyl-5a,6,6a,6b,7,8,9,9a,10,11,11a,11b-dodecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-1(4H)-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 2f49b1b2-f62f-476f-abb4-c36fc75ff548
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name 15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-10,15-dihydroxy-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)(C2(CCC3C2(CCC4C3C(C5C6(C4(C(=O)C=CC6)C)O5)O)C)O)O)C
SMILES (Isomeric) CC1=C(C(=O)OC(C1)C(C)(C2(CCC3C2(CCC4C3C(C5C6(C4(C(=O)C=CC6)C)O5)O)C)O)O)C
InChI InChI=1S/C28H38O7/c1-14-13-19(34-23(31)15(14)2)26(5,32)28(33)12-9-16-20-17(8-11-24(16,28)3)25(4)18(29)7-6-10-27(25)22(35-27)21(20)30/h6-7,16-17,19-22,30,32-33H,8-13H2,1-5H3
InChI Key JDXYJGMBBZUXJW-UHFFFAOYSA-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 1.80
Atomic LogP (AlogP) 2.61
H-Bond Acceptor 7
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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9-[1-(4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-6,9-dihydroxy-9a,11b-dimethyl-5a,6,6a,6b,7,8,9,9a,10,11,11a,11b-dodecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-1(4H)-one #
Ergosta-2,24-dien-26-oic acid, 5,6-epoxy-7,17,20,22-tetrahydroxy-1-oxo-, .delta.-lactone, (5.alpha.,6.alpha.,7.alpha.,22R)-

2D Structure

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2D Structure of 9-[1-(4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-6,9-dihydroxy-9a,11b-dimethyl-5a,6,6a,6b,7,8,9,9a,10,11,11a,11b-dodecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-1(4H)-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9242 92.42%
Caco-2 - 0.6836 68.36%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.6918 69.18%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8837 88.37%
OATP1B3 inhibitior + 0.9140 91.40%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6374 63.74%
BSEP inhibitior + 0.8462 84.62%
P-glycoprotein inhibitior + 0.5888 58.88%
P-glycoprotein substrate + 0.5187 51.87%
CYP3A4 substrate + 0.7190 71.90%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8924 89.24%
CYP3A4 inhibition - 0.7395 73.95%
CYP2C9 inhibition - 0.8398 83.98%
CYP2C19 inhibition - 0.8590 85.90%
CYP2D6 inhibition - 0.9534 95.34%
CYP1A2 inhibition - 0.7647 76.47%
CYP2C8 inhibition + 0.5323 53.23%
CYP inhibitory promiscuity - 0.9846 98.46%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5631 56.31%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.9392 93.92%
Skin irritation + 0.5589 55.89%
Skin corrosion - 0.9047 90.47%
Ames mutagenesis - 0.6483 64.83%
Human Ether-a-go-go-Related Gene inhibition + 0.7514 75.14%
Micronuclear - 0.7000 70.00%
Hepatotoxicity + 0.5858 58.58%
skin sensitisation - 0.8202 82.02%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity + 0.7774 77.74%
Acute Oral Toxicity (c) I 0.4073 40.73%
Estrogen receptor binding + 0.8132 81.32%
Androgen receptor binding + 0.7627 76.27%
Thyroid receptor binding + 0.5896 58.96%
Glucocorticoid receptor binding + 0.7483 74.83%
Aromatase binding + 0.8005 80.05%
PPAR gamma + 0.6621 66.21%
Honey bee toxicity - 0.7975 79.75%
Biodegradation - 0.9500 95.00%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity + 0.9804 98.04%

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 96.35% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.14% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.54% 91.11%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 93.76% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.06% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.96% 99.23%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.93% 85.14%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 89.33% 93.04%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.88% 89.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 87.72% 93.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.77% 95.89%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.49% 97.09%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 83.84% 90.93%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 82.25% 96.09%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.54% 94.00%
CHEMBL2581 P07339 Cathepsin D 81.39% 98.95%
CHEMBL2996 Q05655 Protein kinase C delta 81.25% 97.79%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.16% 86.33%
CHEMBL1871 P10275 Androgen Receptor 80.60% 96.43%
CHEMBL5103 Q969S8 Histone deacetylase 10 80.56% 90.08%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.43% 93.03%

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 592382
LOTUS LTS0226632
wikiData Q105125847