[(1S,2S,4S,5R,7S,9S,10R,11S,12S,14S,15S,16R,17S,19S)-10-acetyloxy-5,17-dihydroxy-16-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-11,15-dimethyl-3,8-dioxahexacyclo[10.7.0.02,4.05,11.07,9.015,19]nonadecan-14-yl] acetate

Details

• Internal ID: 312c4f5a-ab1f-4125-95c3-9df500a6301d
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: [(1S,2S,4S,5R,7S,9S,10R,11S,12S,14S,15S,16R,17S,19S)-10-acetyloxy-5,17-dihydroxy-16-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-11,15-dimethyl-3,8-dioxahexacyclo[10.7.0.02,4.05,11.07,9.015,19]nonadecan-14-yl] acetate
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)C2C(CC3C2(C(CC4C3C5C(O5)C6(C4(C(C7C(C6)O7)OC(=O)C)C)O)OC(=O)C)C)O)CO
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2[C@H](C[C@@H]3[C@@]2([C@H](C[C@H]4[C@H]3[C@H]5[C@H](O5)[C@@]6([C@@]4([C@H]([C@@H]7[C@H](C6)O7)OC(=O)C)C)O)OC(=O)C)C)O)CO
• InChI: InChI=1S/C32H44O11/c1-12-7-20(42-29(37)16(12)11-33)13(2)24-19(36)8-17-23-18(9-22(30(17,24)5)39-14(3)34)31(6)27(40-15(4)35)25-21(41-25)10-32(31,38)28-26(23)43-28/h13,17-28,33,36,38H,7-11H2,1-6H3/t13-,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27+,28+,30-,31+,32+/m1/s1
• InChI Key: LIEJWRQNKMQXKO-LVOOKTNHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₄O₁₁
• Molecular Weight: 604.70 g/mol
• Exact Mass: 604.28836222 g/mol
• Topological Polar Surface Area (TPSA): 165.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.44
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 913263-85-1
• orb2563957
• TN7869

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9327	93.27%
Caco-2	-	0.8352	83.52%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6931	69.31%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8535	85.35%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7371	73.71%
P-glycoprotein inhibitior	+	0.6680	66.80%
P-glycoprotein substrate	+	0.6294	62.94%
CYP3A4 substrate	+	0.7124	71.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9027	90.27%
CYP3A4 inhibition	-	0.6489	64.89%
CYP2C9 inhibition	-	0.8711	87.11%
CYP2C19 inhibition	-	0.9204	92.04%
CYP2D6 inhibition	-	0.9488	94.88%
CYP1A2 inhibition	-	0.8516	85.16%
CYP2C8 inhibition	+	0.5389	53.89%
CYP inhibitory promiscuity	-	0.9129	91.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6055	60.55%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9195	91.95%
Skin irritation	-	0.5179	51.79%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	+	0.5026	50.26%
Human Ether-a-go-go-Related Gene inhibition	-	0.4515	45.15%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.5468	54.68%
skin sensitisation	-	0.8647	86.47%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.7959	79.59%
Acute Oral Toxicity (c)	I	0.7786	77.86%
Estrogen receptor binding	+	0.7593	75.93%
Androgen receptor binding	+	0.6860	68.60%
Thyroid receptor binding	-	0.5568	55.68%
Glucocorticoid receptor binding	+	0.7521	75.21%
Aromatase binding	+	0.7402	74.02%
PPAR gamma	+	0.6647	66.47%
Honey bee toxicity	-	0.6383	63.83%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9699	96.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.04%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.71%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.28%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	93.16%	97.79%
CHEMBL299	P17252	Protein kinase C alpha	91.39%	98.03%
CHEMBL2581	P07339	Cathepsin D	91.33%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.14%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.03%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.90%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.78%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.26%	95.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.27%	97.25%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.95%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.48%	99.23%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.15%	90.08%
CHEMBL340	P08684	Cytochrome P450 3A4	85.31%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.26%	96.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.06%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.94%	89.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.68%	98.75%
CHEMBL1914	P06276	Butyrylcholinesterase	82.43%	95.00%
CHEMBL5028	O14672	ADAM10	81.89%	97.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.75%	91.24%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.02%	97.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.97%	94.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.80%	89.50%
CHEMBL1937	Q92769	Histone deacetylase 2	80.60%	94.75%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.56%	93.56%

Plants that contains it

• Tacca plantaginea

Cross-Links

• PubChem: 16079919
• LOTUS: LTS0028574
• wikiData: Q105152141