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(2S)-2-[(1R)-1-[(4S,9S,10R,13S,17S)-4,17-dihydroxy-10,13-dimethyl-1-oxo-7,9,11,12,15,16-hexahydro-4H-cyclopenta[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 b3207ef4-940f-4d24-9562-87b406d27347
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2S)-2-[(1R)-1-[(4S,9S,10R,13S,17S)-4,17-dihydroxy-10,13-dimethyl-1-oxo-7,9,11,12,15,16-hexahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2(CCC3=C4CC=C5C(C=CC(=O)C5(C4CCC32C)C)O)O)C
SMILES (Isomeric) CC1=C(C(=O)O[C@@H](C1)[C@@H](C)[C@]2(CCC3=C4CC=C5[C@H](C=CC(=O)[C@@]5([C@H]4CC[C@@]32C)C)O)O)C
InChI InChI=1S/C28H36O5/c1-15-14-23(33-25(31)16(15)2)17(3)28(32)13-11-19-18-6-7-21-22(29)8-9-24(30)27(21,5)20(18)10-12-26(19,28)4/h7-9,17,20,22-23,29,32H,6,10-14H2,1-5H3/t17-,20+,22+,23+,26+,27-,28+/m1/s1
InChI Key OBDQWQCFPJHUIL-NLQXTNLWSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H36O5
Molecular Weight 452.60 g/mol
Exact Mass 452.25627424 g/mol
Topological Polar Surface Area (TPSA) 83.80 Ų
XlogP 2.60
Atomic LogP (AlogP) 4.35
H-Bond Acceptor 5
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 (2S)-2-[(1R)-1-[(4S,9S,10R,13S,17S)-4,17-dihydroxy-10,13-dimethyl-1-oxo-7,9,11,12,15,16-hexahydro-4H-cyclopenta[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 + 0.9820 98.20%
Caco-2 - 0.5985 59.85%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7937 79.37%
OATP2B1 inhibitior - 0.8610 86.10%
OATP1B1 inhibitior + 0.8614 86.14%
OATP1B3 inhibitior + 0.9122 91.22%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.5374 53.74%
BSEP inhibitior + 0.9126 91.26%
P-glycoprotein inhibitior + 0.6816 68.16%
P-glycoprotein substrate - 0.5144 51.44%
CYP3A4 substrate + 0.6959 69.59%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9113 91.13%
CYP3A4 inhibition - 0.7206 72.06%
CYP2C9 inhibition - 0.9373 93.73%
CYP2C19 inhibition - 0.9626 96.26%
CYP2D6 inhibition - 0.9662 96.62%
CYP1A2 inhibition - 0.7647 76.47%
CYP2C8 inhibition - 0.5656 56.56%
CYP inhibitory promiscuity - 0.9700 97.00%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5638 56.38%
Eye corrosion - 0.9935 99.35%
Eye irritation - 0.9549 95.49%
Skin irritation + 0.7083 70.83%
Skin corrosion - 0.9110 91.10%
Ames mutagenesis - 0.6970 69.70%
Human Ether-a-go-go-Related Gene inhibition + 0.6546 65.46%
Micronuclear - 0.7600 76.00%
Hepatotoxicity + 0.5482 54.82%
skin sensitisation - 0.8078 80.78%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.9750 97.50%
Nephrotoxicity + 0.7422 74.22%
Acute Oral Toxicity (c) I 0.6059 60.59%
Estrogen receptor binding + 0.8361 83.61%
Androgen receptor binding + 0.7355 73.55%
Thyroid receptor binding + 0.6756 67.56%
Glucocorticoid receptor binding + 0.8326 83.26%
Aromatase binding + 0.6677 66.77%
PPAR gamma + 0.5687 56.87%
Honey bee toxicity - 0.7777 77.77%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9862 98.62%

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 97.16% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.63% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.03% 95.56%
CHEMBL2581 P07339 Cathepsin D 88.42% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.35% 95.89%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.75% 85.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.98% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 85.85% 96.09%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.70% 97.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.37% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.06% 99.23%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 83.80% 90.71%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.18% 94.45%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 82.87% 93.03%
CHEMBL3359 P21462 Formyl peptide receptor 1 81.69% 93.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.06% 97.09%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.40% 93.04%
CHEMBL2964 P36507 Dual specificity mitogen-activated protein kinase kinase 2 80.36% 80.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.33% 94.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.28% 91.07%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.09% 86.33%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 80.07% 96.47%

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 162890605
LOTUS LTS0206640
wikiData Q105188960