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(2R)-2-[(1S)-1-hydroxy-1-[(8R,9S,10R,13S,14R,15S,17S)-14,15,17-trihydroxy-10,13-dimethyl-1-oxo-2,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-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 9d099e31-cf31-401e-ae7f-72285e2950f5
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1S)-1-hydroxy-1-[(8R,9S,10R,13S,14R,15S,17S)-14,15,17-trihydroxy-10,13-dimethyl-1-oxo-2,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)(C2(CC(C3(C2(CCC4C3CC=C5C4(C(=O)CC=C5)C)C)O)O)O)O)C
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@@]2(C[C@@H]([C@@]3([C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(C(=O)CC=C5)C)C)O)O)O)O)C
InChI InChI=1S/C28H38O7/c1-15-13-22(35-23(31)16(15)2)26(5,32)27(33)14-21(30)28(34)19-10-9-17-7-6-8-20(29)25(17,4)18(19)11-12-24(27,28)3/h6-7,9,18-19,21-22,30,32-34H,8,10-14H2,1-5H3/t18-,19+,21-,22+,24+,25-,26-,27-,28-/m0/s1
InChI Key QKOOJURCARFMON-VLXOZLMASA-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) 124.00 Ų
XlogP 1.40
Atomic LogP (AlogP) 2.51
H-Bond Acceptor 7
H-Bond Donor 4
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-2-[(1S)-1-hydroxy-1-[(8R,9S,10R,13S,14R,15S,17S)-14,15,17-trihydroxy-10,13-dimethyl-1-oxo-2,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9129 91.29%
Caco-2 - 0.6706 67.06%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.7508 75.08%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8842 88.42%
OATP1B3 inhibitior + 0.9021 90.21%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6124 61.24%
BSEP inhibitior + 0.8492 84.92%
P-glycoprotein inhibitior + 0.5807 58.07%
P-glycoprotein substrate + 0.5477 54.77%
CYP3A4 substrate + 0.7200 72.00%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9091 90.91%
CYP3A4 inhibition - 0.8102 81.02%
CYP2C9 inhibition - 0.9188 91.88%
CYP2C19 inhibition - 0.9084 90.84%
CYP2D6 inhibition - 0.9525 95.25%
CYP1A2 inhibition - 0.8466 84.66%
CYP2C8 inhibition + 0.5200 52.00%
CYP inhibitory promiscuity - 0.9794 97.94%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5917 59.17%
Eye corrosion - 0.9919 99.19%
Eye irritation - 0.9508 95.08%
Skin irritation + 0.6663 66.63%
Skin corrosion - 0.9078 90.78%
Ames mutagenesis - 0.6837 68.37%
Human Ether-a-go-go-Related Gene inhibition + 0.7334 73.34%
Micronuclear - 0.7600 76.00%
Hepatotoxicity + 0.6607 66.07%
skin sensitisation - 0.8497 84.97%
Respiratory toxicity + 0.7889 78.89%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity + 0.8107 81.07%
Acute Oral Toxicity (c) I 0.4263 42.63%
Estrogen receptor binding + 0.8500 85.00%
Androgen receptor binding + 0.7567 75.67%
Thyroid receptor binding + 0.6450 64.50%
Glucocorticoid receptor binding + 0.7884 78.84%
Aromatase binding + 0.8080 80.80%
PPAR gamma + 0.6222 62.22%
Honey bee toxicity - 0.8300 83.00%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.6800 68.00%
Fish aquatic toxicity + 0.9797 97.97%

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 97.98% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 92.61% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.76% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 91.73% 99.23%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.82% 100.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.87% 97.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.84% 86.33%
CHEMBL3359 P21462 Formyl peptide receptor 1 86.59% 93.56%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 86.54% 93.03%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 86.47% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.08% 89.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.16% 93.04%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.85% 94.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.61% 97.09%
CHEMBL1937 Q92769 Histone deacetylase 2 84.36% 94.75%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 82.51% 82.69%
CHEMBL3401 O75469 Pregnane X receptor 82.34% 94.73%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.26% 95.89%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 80.94% 100.00%
CHEMBL1871 P10275 Androgen Receptor 80.29% 96.43%

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 coagulans

Cross-Links

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PubChem 162896387
LOTUS LTS0086613
wikiData Q105223246