[3-Acetyloxy-5-hydroxy-2-[[14-hydroxy-7,7,12,16-tetramethyl-15-[2-methyl-5-[2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]oxolan-2-yl]-9-(3,4,5-trihydroxyoxan-2-yl)oxy-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]oxan-4-yl] acetate

Details

• Internal ID: 3d390907-bc43-472d-af0d-49429c12974d
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [3-acetyloxy-5-hydroxy-2-[[14-hydroxy-7,7,12,16-tetramethyl-15-[2-methyl-5-[2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]oxolan-2-yl]-9-(3,4,5-trihydroxyoxan-2-yl)oxy-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]oxan-4-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(COC(C1OC(=O)C)OC2CCC34CC35CCC6(C(C(CC6(C5CC(C4C2(C)C)OC7C(C(C(CO7)O)O)O)C)O)C8(CCC(O8)C(C)(C)OC9C(C(C(C(O9)CO)O)O)O)C)C)O
• SMILES (Isomeric): CC(=O)OC1C(COC(C1OC(=O)C)OC2CCC34CC35CCC6(C(C(CC6(C5CC(C4C2(C)C)OC7C(C(C(CO7)O)O)O)C)O)C8(CCC(O8)C(C)(C)OC9C(C(C(C(O9)CO)O)O)O)C)C)O
• InChI: InChI=1S/C50H80O20/c1-22(52)64-37-26(56)20-63-43(38(37)65-23(2)53)68-30-11-13-50-21-49(50)15-14-46(7)39(48(9)12-10-31(69-48)45(5,6)70-42-36(61)34(59)33(58)28(18-51)67-42)24(54)17-47(46,8)29(49)16-27(40(50)44(30,3)4)66-41-35(60)32(57)25(55)19-62-41/h24-43,51,54-61H,10-21H2,1-9H3
• InChI Key: XELJHBPJGYZIGB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₈₀O₂₀
• Molecular Weight: 1001.20 g/mol
• Exact Mass: 1000.52429494 g/mol
• Topological Polar Surface Area (TPSA): 299.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.33
• H-Bond Acceptor: 20
• H-Bond Donor: 9
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6958	69.58%
Caco-2	-	0.8773	87.73%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7771	77.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8094	80.94%
OATP1B3 inhibitior	+	0.9416	94.16%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7287	72.87%
BSEP inhibitior	+	0.8185	81.85%
P-glycoprotein inhibitior	+	0.7551	75.51%
P-glycoprotein substrate	+	0.5644	56.44%
CYP3A4 substrate	+	0.7443	74.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8780	87.80%
CYP3A4 inhibition	-	0.7216	72.16%
CYP2C9 inhibition	-	0.7822	78.22%
CYP2C19 inhibition	-	0.8524	85.24%
CYP2D6 inhibition	-	0.9466	94.66%
CYP1A2 inhibition	-	0.9082	90.82%
CYP2C8 inhibition	+	0.7205	72.05%
CYP inhibitory promiscuity	-	0.9558	95.58%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6430	64.30%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9019	90.19%
Skin irritation	-	0.7028	70.28%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.5570	55.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7678	76.78%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5834	58.34%
skin sensitisation	-	0.9164	91.64%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8959	89.59%
Acute Oral Toxicity (c)	I	0.6455	64.55%
Estrogen receptor binding	+	0.7649	76.49%
Androgen receptor binding	+	0.7538	75.38%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7573	75.73%
Aromatase binding	+	0.6577	65.77%
PPAR gamma	+	0.8007	80.07%
Honey bee toxicity	-	0.6116	61.16%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9297	92.97%

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	98.90%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.54%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.79%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.94%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.67%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.58%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.35%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.95%	96.95%
CHEMBL259	P32245	Melanocortin receptor 4	90.88%	95.38%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.94%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	88.48%	95.93%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.18%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	87.55%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.36%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.34%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	86.15%	92.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.00%	97.14%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	85.68%	82.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.57%	91.07%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.14%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.00%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.79%	95.50%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.67%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.14%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.76%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.41%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.29%	92.62%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.63%	96.21%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.34%	91.03%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.26%	94.62%
CHEMBL237	P41145	Kappa opioid receptor	80.18%	98.10%

Plants that contains it

• Astragalus armatus

Cross-Links

• PubChem: 162938394
• LOTUS: LTS0012515
• wikiData: Q105326412