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

Details

• Internal ID: f962f4f9-a4a4-431d-8175-aa6a310507c3
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: [(5R,6R,8R,9S,10R,13R,14R,15S)-17-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5,6,14-trihydroxy-10,13-dimethyl-1-oxo-4,6,7,8,9,11,12,15-octahydrocyclopenta[a]phenanthren-15-yl] acetate
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)C2=CC(C3(C2(CCC4C3CC(C5(C4(C(=O)C=CC5)C)O)O)C)O)OC(=O)C)C
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@H](C)C2=C[C@@H]([C@@]3([C@@]2(CC[C@H]4[C@H]3C[C@H]([C@@]5([C@@]4(C(=O)C=CC5)C)O)O)C)O)OC(=O)C)C
• InChI: InChI=1S/C30H40O8/c1-15-12-22(38-26(34)16(15)2)17(3)20-14-25(37-18(4)31)30(36)21-13-24(33)29(35)10-7-8-23(32)28(29,6)19(21)9-11-27(20,30)5/h7-8,14,17,19,21-22,24-25,33,35-36H,9-13H2,1-6H3/t17-,19-,21+,22+,24+,25-,27+,28-,29-,30-/m0/s1
• InChI Key: REOWXEUUAXLCRM-DTRRUJLXSA-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: 1.90
• Atomic LogP (AlogP): 2.94
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9380	93.80%
Caco-2	-	0.7113	71.13%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7741	77.41%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8617	86.17%
OATP1B3 inhibitior	+	0.8809	88.09%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6624	66.24%
BSEP inhibitior	+	0.9569	95.69%
P-glycoprotein inhibitior	+	0.7572	75.72%
P-glycoprotein substrate	+	0.6308	63.08%
CYP3A4 substrate	+	0.7258	72.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9121	91.21%
CYP3A4 inhibition	-	0.7787	77.87%
CYP2C9 inhibition	-	0.8955	89.55%
CYP2C19 inhibition	-	0.8484	84.84%
CYP2D6 inhibition	-	0.9550	95.50%
CYP1A2 inhibition	-	0.6828	68.28%
CYP2C8 inhibition	+	0.6303	63.03%
CYP inhibitory promiscuity	-	0.9740	97.40%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6260	62.60%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9383	93.83%
Skin irritation	+	0.6456	64.56%
Skin corrosion	-	0.9183	91.83%
Ames mutagenesis	-	0.6223	62.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.5327	53.27%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5176	51.76%
skin sensitisation	-	0.8549	85.49%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.6193	61.93%
Acute Oral Toxicity (c)	I	0.5210	52.10%
Estrogen receptor binding	+	0.8383	83.83%
Androgen receptor binding	+	0.7534	75.34%
Thyroid receptor binding	+	0.5538	55.38%
Glucocorticoid receptor binding	+	0.8118	81.18%
Aromatase binding	+	0.7504	75.04%
PPAR gamma	+	0.6792	67.92%
Honey bee toxicity	-	0.7173	71.73%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9840	98.40%

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	93.37%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.67%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.02%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.51%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.49%	97.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.29%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.59%	99.23%
CHEMBL2996	Q05655	Protein kinase C delta	88.82%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.46%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.38%	100.00%
CHEMBL2581	P07339	Cathepsin D	87.06%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.90%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.46%	94.45%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.38%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.13%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.83%	93.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.58%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	84.30%	91.19%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.11%	95.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.00%	91.07%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.16%	90.08%

Plants that contains it

• Physalis angulata
• Physalis lagascae
• Physalis minima

Cross-Links

• PubChem: 14216306
• LOTUS: LTS0035811
• wikiData: Q104397898