(1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R,4S,5R)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one

Details

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Internal ID 9c97bb74-3f13-46ff-a232-1d48d5a07e3e
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R,4S,5R)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
SMILES (Canonical) CC1CC(OC(=O)C1C)C(C)(C2CCC3C2(CCC4C3C5C(O5)C6(C4(C(=O)C=CC6)C)O)C)O
SMILES (Isomeric) C[C@H]1C[C@@H](OC(=O)[C@@H]1C)[C@@](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(=O)C=CC6)C)O)C)O
InChI InChI=1S/C28H40O6/c1-14-13-20(33-24(30)15(14)2)27(5,31)18-9-8-16-21-17(10-12-25(16,18)3)26(4)19(29)7-6-11-28(26,32)23-22(21)34-23/h6-7,14-18,20-23,31-32H,8-13H2,1-5H3/t14-,15+,16-,17-,18-,20+,21-,22-,23-,25-,26-,27+,28-/m0/s1
InChI Key MLMDWCVFKUVZGH-AKAZKRMISA-N
Popularity 1 reference 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 3.80
Atomic LogP (AlogP) 3.43
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 2

Synonyms

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DTXSID701120280
108157-59-1
Ergost-2-en-26-oic acid, 6,7-epoxy-5,20,22-trihydroxy-1-oxo-, delta-lactone, (5alpha,6alpha,7alpha,22R,25R)-

2D Structure

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2D Structure of (1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R,4S,5R)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9298 92.98%
Caco-2 - 0.6427 64.27%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.6796 67.96%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8780 87.80%
OATP1B3 inhibitior + 0.8509 85.09%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7571 75.71%
BSEP inhibitior + 0.6557 65.57%
P-glycoprotein inhibitior - 0.4323 43.23%
P-glycoprotein substrate - 0.5186 51.86%
CYP3A4 substrate + 0.7260 72.60%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9084 90.84%
CYP3A4 inhibition - 0.7528 75.28%
CYP2C9 inhibition - 0.8922 89.22%
CYP2C19 inhibition - 0.8865 88.65%
CYP2D6 inhibition - 0.9634 96.34%
CYP1A2 inhibition - 0.7312 73.12%
CYP2C8 inhibition - 0.6040 60.40%
CYP inhibitory promiscuity - 0.9871 98.71%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5739 57.39%
Eye corrosion - 0.9913 99.13%
Eye irritation - 0.9492 94.92%
Skin irritation + 0.5247 52.47%
Skin corrosion - 0.8870 88.70%
Ames mutagenesis - 0.6900 69.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6706 67.06%
Micronuclear - 0.7200 72.00%
Hepatotoxicity + 0.6333 63.33%
skin sensitisation - 0.8589 85.89%
Respiratory toxicity + 0.8556 85.56%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.6914 69.14%
Acute Oral Toxicity (c) I 0.4409 44.09%
Estrogen receptor binding + 0.8068 80.68%
Androgen receptor binding + 0.7302 73.02%
Thyroid receptor binding + 0.5930 59.30%
Glucocorticoid receptor binding + 0.6929 69.29%
Aromatase binding + 0.6848 68.48%
PPAR gamma + 0.5994 59.94%
Honey bee toxicity - 0.8270 82.70%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.6400 64.00%
Fish aquatic toxicity + 0.9693 96.93%

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 99.13% 97.25%
CHEMBL4040 P28482 MAP kinase ERK2 97.21% 83.82%
CHEMBL230 P35354 Cyclooxygenase-2 94.19% 89.63%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.97% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.18% 91.11%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.99% 100.00%
CHEMBL2039 P27338 Monoamine oxidase B 92.69% 92.51%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 91.14% 93.40%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 90.65% 97.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.52% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.31% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.87% 86.33%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 88.55% 93.04%
CHEMBL1871 P10275 Androgen Receptor 87.85% 96.43%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.34% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.31% 89.00%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 85.06% 90.93%
CHEMBL2996 Q05655 Protein kinase C delta 84.60% 97.79%
CHEMBL1937 Q92769 Histone deacetylase 2 83.95% 94.75%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.26% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.91% 99.23%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 80.84% 96.77%

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.
Physalis philadelphica
Withania somnifera

Cross-Links

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PubChem 14605185
LOTUS LTS0153006
wikiData Q105166828