[(5R,6R,8R,9S,10R,13R,14R,17S)-17-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5,6,14,17-tetrahydroxy-10-methyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-13-yl]methyl acetate

Details

• Internal ID: 112413c9-b66b-4112-8afc-7f8310ea9a42
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: [(5R,6R,8R,9S,10R,13R,14R,17S)-17-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5,6,14,17-tetrahydroxy-10-methyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-13-yl]methyl acetate
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2(CCC3(C2(CCC4C3CC(C5(C4(C(=O)C=CC5)C)O)O)COC(=O)C)O)O)O)C
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@@]2(CC[C@@]3([C@@]2(CC[C@H]4[C@H]3C[C@H]([C@@]5([C@@]4(C(=O)C=CC5)C)O)O)COC(=O)C)O)O)O)C
• InChI: InChI=1S/C30H42O10/c1-16-13-23(40-24(34)17(16)2)26(5,35)30(38)12-11-28(36)20-14-22(33)29(37)9-6-7-21(32)25(29,4)19(20)8-10-27(28,30)15-39-18(3)31/h6-7,19-20,22-23,33,35-38H,8-15H2,1-5H3/t19-,20+,22+,23+,25-,26-,27+,28+,29-,30+/m0/s1
• InChI Key: JTCXLPXXHYHANN-SRPSTUDXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₂O₁₀
• Molecular Weight: 562.60 g/mol
• Exact Mass: 562.27779753 g/mol
• Topological Polar Surface Area (TPSA): 171.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 1.25
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8398	83.98%
Caco-2	-	0.7793	77.93%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8194	81.94%
OATP2B1 inhibitior	-	0.7234	72.34%
OATP1B1 inhibitior	+	0.8676	86.76%
OATP1B3 inhibitior	+	0.9385	93.85%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6622	66.22%
BSEP inhibitior	+	0.9425	94.25%
P-glycoprotein inhibitior	+	0.6532	65.32%
P-glycoprotein substrate	+	0.6556	65.56%
CYP3A4 substrate	+	0.7367	73.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9121	91.21%
CYP3A4 inhibition	-	0.8756	87.56%
CYP2C9 inhibition	-	0.8888	88.88%
CYP2C19 inhibition	-	0.9144	91.44%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.8562	85.62%
CYP2C8 inhibition	+	0.6053	60.53%
CYP inhibitory promiscuity	-	0.9406	94.06%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7164	71.64%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9268	92.68%
Skin irritation	+	0.6057	60.57%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.5607	56.07%
Human Ether-a-go-go-Related Gene inhibition	+	0.6672	66.72%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.5195	51.95%
skin sensitisation	-	0.9254	92.54%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.7375	73.75%
Acute Oral Toxicity (c)	I	0.5148	51.48%
Estrogen receptor binding	+	0.8153	81.53%
Androgen receptor binding	+	0.7738	77.38%
Thyroid receptor binding	+	0.5287	52.87%
Glucocorticoid receptor binding	+	0.7613	76.13%
Aromatase binding	+	0.7636	76.36%
PPAR gamma	+	0.6450	64.50%
Honey bee toxicity	-	0.7798	77.98%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9790	97.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.55%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.89%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	96.57%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.38%	91.11%
CHEMBL230	P35354	Cyclooxygenase-2	94.05%	89.63%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.60%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.25%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.15%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.84%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.34%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.68%	86.33%
CHEMBL2581	P07339	Cathepsin D	87.80%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.60%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	87.20%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.03%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	85.86%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.96%	95.89%
CHEMBL5028	O14672	ADAM10	84.02%	97.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.84%	93.04%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	83.47%	90.93%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.77%	92.62%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.42%	82.69%
CHEMBL3401	O75469	Pregnane X receptor	81.67%	94.73%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.89%	95.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.41%	93.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.18%	91.07%

Plants that contains it

• Physalis peruviana

Cross-Links

• PubChem: 162988289
• LOTUS: LTS0092942
• wikiData: Q105134715