27-Hydroxywithanone

Details

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Internal ID ad9fd39d-edd4-4b36-bdf3-ed771d848a2a
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)-5,15-dihydroxy-15-[(1R)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2(CCC3C2(CCC4C3C5C(O5)C6(C4(C(=O)C=CC6)C)O)C)O)CO
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@]2(CC[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)CO
InChI InChI=1S/C28H38O7/c1-14-12-19(34-24(31)16(14)13-29)15(2)27(32)11-8-17-21-18(7-10-25(17,27)3)26(4)20(30)6-5-9-28(26,33)23-22(21)35-23/h5-6,15,17-19,21-23,29,32-33H,7-13H2,1-4H3/t15-,17+,18+,19-,21+,22+,23+,25+,26+,27+,28+/m1/s1
InChI Key XOKCBESGXYESDY-LGZUTLPBSA-N
Popularity 1 reference 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 2.40
Atomic LogP (AlogP) 2.47
H-Bond Acceptor 7
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

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27-Hydroxy withanone
67N9QT9KEZ
UNII-67N9QT9KEZ
871949-32-5
CHEMBL4518693
CHEBI:193033
Q27264151

2D Structure

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2D Structure of 27-Hydroxywithanone

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9375 93.75%
Caco-2 - 0.6765 67.65%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.7446 74.46%
OATP2B1 inhibitior - 0.8599 85.99%
OATP1B1 inhibitior + 0.8339 83.39%
OATP1B3 inhibitior + 0.9469 94.69%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.5796 57.96%
BSEP inhibitior + 0.9612 96.12%
P-glycoprotein inhibitior + 0.6270 62.70%
P-glycoprotein substrate + 0.5588 55.88%
CYP3A4 substrate + 0.6929 69.29%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9063 90.63%
CYP3A4 inhibition - 0.6949 69.49%
CYP2C9 inhibition - 0.8257 82.57%
CYP2C19 inhibition - 0.9233 92.33%
CYP2D6 inhibition - 0.9540 95.40%
CYP1A2 inhibition - 0.8616 86.16%
CYP2C8 inhibition - 0.5601 56.01%
CYP inhibitory promiscuity - 0.9602 96.02%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5686 56.86%
Eye corrosion - 0.9906 99.06%
Eye irritation - 0.9526 95.26%
Skin irritation + 0.5650 56.50%
Skin corrosion - 0.9359 93.59%
Ames mutagenesis - 0.6553 65.53%
Human Ether-a-go-go-Related Gene inhibition + 0.6912 69.12%
Micronuclear - 0.7300 73.00%
Hepatotoxicity + 0.6126 61.26%
skin sensitisation - 0.8981 89.81%
Respiratory toxicity + 0.8556 85.56%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity + 0.6007 60.07%
Acute Oral Toxicity (c) I 0.5711 57.11%
Estrogen receptor binding + 0.8286 82.86%
Androgen receptor binding + 0.7631 76.31%
Thyroid receptor binding + 0.6433 64.33%
Glucocorticoid receptor binding + 0.7709 77.09%
Aromatase binding + 0.7251 72.51%
PPAR gamma + 0.6634 66.34%
Honey bee toxicity - 0.7982 79.82%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.9586 95.86%

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 97.46% 97.25%
CHEMBL4072 P07858 Cathepsin B 95.97% 93.67%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.70% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.80% 95.56%
CHEMBL2581 P07339 Cathepsin D 93.53% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.23% 96.09%
CHEMBL1937 Q92769 Histone deacetylase 2 92.15% 94.75%
CHEMBL2996 Q05655 Protein kinase C delta 90.10% 97.79%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.56% 97.09%
CHEMBL5103 Q969S8 Histone deacetylase 10 89.46% 90.08%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 89.43% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.05% 100.00%
CHEMBL3310 Q96DB2 Histone deacetylase 11 86.47% 88.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.12% 86.33%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.70% 93.04%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.84% 99.23%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.66% 95.89%
CHEMBL3359 P21462 Formyl peptide receptor 1 83.90% 93.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.74% 89.00%
CHEMBL3192 Q9BY41 Histone deacetylase 8 81.10% 93.99%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 80.66% 94.80%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 80.52% 90.71%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.11% 100.00%

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 21574483
LOTUS LTS0027945
wikiData Q27264151