[(1S,2S,3R,5S,7S,9S,10R,11S,12S,13S,14R,15R,16S,17S,22S,23S,24R,25R)-3,10,13-triacetyloxy-5,14,22-trihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.02,12.05,11.07,9.016,24.019,23]pentacos-18-en-25-yl] acetate

Details

• Internal ID: b6babac9-489d-483f-894e-2015bb9e0881
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: [(1S,2S,3R,5S,7S,9S,10R,11S,12S,13S,14R,15R,16S,17S,22S,23S,24R,25R)-3,10,13-triacetyloxy-5,14,22-trihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.02,12.05,11.07,9.016,24.019,23]pentacos-18-en-25-yl] acetate
• SMILES (Canonical): CC1C=C2C(C3C1C4(C(C3OC(=O)C)C5C(C(C4O)OC(=O)C)C6(C(C7C(O7)CC6(C(=O)C5OC(=O)C)O)OC(=O)C)C)C)(C(C(=O)O2)(C)O)C
• SMILES (Isomeric): C[C@@H]1C=C2[C@@]([C@H]3[C@H]1[C@@]4([C@@H]([C@H]3OC(=O)C)[C@H]5[C@H]([C@@H]([C@@H]4O)OC(=O)C)[C@]6([C@H]([C@@H]7[C@@H](O7)C[C@]6(C(=O)[C@@H]5OC(=O)C)O)OC(=O)C)C)C)([C@](C(=O)O2)(C)O)C
• InChI: InChI=1S/C36H46O15/c1-12-10-18-33(7,35(9,44)31(43)51-18)23-20(12)32(6)21(26(23)47-14(3)38)19-22(27(28(32)41)48-15(4)39)34(8)30(49-16(5)40)24-17(50-24)11-36(34,45)29(42)25(19)46-13(2)37/h10,12,17,19-28,30,41,44-45H,11H2,1-9H3/t12-,17+,19+,20+,21-,22-,23+,24+,25-,26-,27+,28+,30+,32-,33+,34+,35-,36-/m1/s1
• InChI Key: GLBBNXPRMRGGIZ-PLTXRRTJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₆O₁₅
• Molecular Weight: 718.70 g/mol
• Exact Mass: 718.28367076 g/mol
• Topological Polar Surface Area (TPSA): 222.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.53
• H-Bond Acceptor: 15
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9882	98.82%
Caco-2	-	0.8292	82.92%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6566	65.66%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.8436	84.36%
OATP1B3 inhibitior	+	0.9064	90.64%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9481	94.81%
P-glycoprotein inhibitior	+	0.7998	79.98%
P-glycoprotein substrate	-	0.6475	64.75%
CYP3A4 substrate	+	0.7022	70.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8653	86.53%
CYP3A4 inhibition	-	0.7804	78.04%
CYP2C9 inhibition	-	0.9265	92.65%
CYP2C19 inhibition	-	0.9221	92.21%
CYP2D6 inhibition	-	0.9330	93.30%
CYP1A2 inhibition	-	0.9021	90.21%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.8912	89.12%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.5147	51.47%
Eye corrosion	-	0.9831	98.31%
Eye irritation	-	0.8991	89.91%
Skin irritation	-	0.6045	60.45%
Skin corrosion	-	0.8921	89.21%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6569	65.69%
Micronuclear	+	0.5259	52.59%
Hepatotoxicity	+	0.6283	62.83%
skin sensitisation	-	0.7613	76.13%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.8227	82.27%
Acute Oral Toxicity (c)	III	0.3642	36.42%
Estrogen receptor binding	+	0.7585	75.85%
Androgen receptor binding	+	0.7343	73.43%
Thyroid receptor binding	+	0.5545	55.45%
Glucocorticoid receptor binding	+	0.7022	70.22%
Aromatase binding	+	0.6789	67.89%
PPAR gamma	+	0.7134	71.34%
Honey bee toxicity	-	0.7112	71.12%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9409	94.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.15%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.95%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.88%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.23%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.59%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.27%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.54%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.50%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	90.53%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.81%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.20%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.07%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.68%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.53%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.55%	89.00%
CHEMBL4208	P20618	Proteasome component C5	83.28%	90.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.12%	93.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.09%	99.23%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.88%	86.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.78%	89.50%
CHEMBL3401	O75469	Pregnane X receptor	81.53%	94.73%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.49%	85.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.00%	95.50%

Plants that contains it

• Tacca chantrieri

Cross-Links

• PubChem: 163027236
• LOTUS: LTS0037509
• wikiData: Q105010744