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

Details

• Internal ID: 65bf1895-d9aa-481f-9eee-54997d2ca9f1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: [(8R,9S,10R,13R,14R,17S)-17-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-14,17-dihydroxy-10-methyl-1-oxo-4,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-13-yl]methyl acetate
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2(CCC3(C2(CCC4C3CC=C5C4(C(=O)C=CC5)C)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]3CC=C5[C@@]4(C(=O)C=CC5)C)COC(=O)C)O)O)O)C
• InChI: InChI=1S/C30H40O8/c1-17-15-24(38-25(33)18(17)2)27(5,34)30(36)14-13-29(35)22-10-9-20-7-6-8-23(32)26(20,4)21(22)11-12-28(29,30)16-37-19(3)31/h6,8-9,21-22,24,34-36H,7,10-16H2,1-5H3/t21-,22+,24+,26-,27-,28+,29+,30+/m0/s1
• InChI Key: RGHQRULWHKEQHE-GRVQADPTSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₀O₈
• Molecular Weight: 528.60 g/mol
• Exact Mass: 528.27231823 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 3.09
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• SCHEMBL20733500
• BDBM50114395

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8816	88.16%
Caco-2	-	0.7211	72.11%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8491	84.91%
OATP2B1 inhibitior	-	0.8619	86.19%
OATP1B1 inhibitior	+	0.8668	86.68%
OATP1B3 inhibitior	+	0.9193	91.93%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6622	66.22%
BSEP inhibitior	+	0.9610	96.10%
P-glycoprotein inhibitior	+	0.7224	72.24%
P-glycoprotein substrate	+	0.6426	64.26%
CYP3A4 substrate	+	0.7414	74.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9146	91.46%
CYP3A4 inhibition	-	0.8515	85.15%
CYP2C9 inhibition	-	0.8937	89.37%
CYP2C19 inhibition	-	0.9264	92.64%
CYP2D6 inhibition	-	0.9461	94.61%
CYP1A2 inhibition	-	0.8605	86.05%
CYP2C8 inhibition	+	0.6116	61.16%
CYP inhibitory promiscuity	-	0.9412	94.12%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6891	68.91%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9365	93.65%
Skin irritation	+	0.6347	63.47%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7203	72.03%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5732	57.32%
skin sensitisation	-	0.9304	93.04%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7890	78.90%
Acute Oral Toxicity (c)	III	0.4163	41.63%
Estrogen receptor binding	+	0.8264	82.64%
Androgen receptor binding	+	0.7503	75.03%
Thyroid receptor binding	+	0.6152	61.52%
Glucocorticoid receptor binding	+	0.8306	83.06%
Aromatase binding	+	0.7588	75.88%
PPAR gamma	+	0.6220	62.20%
Honey bee toxicity	-	0.7879	78.79%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9812	98.12%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1871	P10275	Androgen Receptor	580 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.56%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.90%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.48%	97.14%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.19%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.69%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.60%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	89.50%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.22%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.29%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.29%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.16%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.68%	97.09%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	86.02%	91.65%
CHEMBL340	P08684	Cytochrome P450 3A4	85.52%	91.19%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.38%	93.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.11%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.03%	96.09%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.18%	95.71%
CHEMBL230	P35354	Cyclooxygenase-2	83.96%	89.63%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.44%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.89%	94.00%
CHEMBL5028	O14672	ADAM10	82.76%	97.50%
CHEMBL4040	P28482	MAP kinase ERK2	82.54%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.97%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.40%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.19%	95.89%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.59%	90.93%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.20%	90.08%

Plants that contains it

• Physalis coztomatl
• Physalis peruviana

Cross-Links

• PubChem: 101883242
• LOTUS: LTS0239597
• wikiData: Q104399272