[(2S,3R,4S,5R)-3-acetyloxy-5-hydroxy-2-[[14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]oxan-4-yl] acetate

Details

• Internal ID: 83db4183-11c4-49a6-bde8-b562bc5f7237
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(2S,3R,4S,5R)-3-acetyloxy-5-hydroxy-2-[[14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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(C(O7)CO)O)O)O)C)O)C8(CCC(O8)C(C)(C)O)C)C)O
• SMILES (Isomeric): CC(=O)O[C@H]1[C@@H](CO[C@H]([C@@H]1OC(=O)C)OC2CCC34CC35CCC6(C(C(CC6(C5CC(C4C2(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)O)C8(CCC(O8)C(C)(C)O)C)C)O
• InChI: InChI=1S/C45H72O16/c1-21(47)56-33-24(50)19-55-38(34(33)57-22(2)48)60-28-11-13-45-20-44(45)15-14-41(7)35(43(9)12-10-29(61-43)40(5,6)54)23(49)17-42(41,8)27(44)16-25(36(45)39(28,3)4)58-37-32(53)31(52)30(51)26(18-46)59-37/h23-38,46,49-54H,10-20H2,1-9H3/t23?,24-,25?,26-,27?,28?,29?,30-,31+,32-,33+,34-,35?,36?,37-,38+,41?,42?,43?,44?,45?/m1/s1
• InChI Key: KXHCYYSIAXMSPA-IWDHDKPASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₂O₁₆
• Molecular Weight: 869.00 g/mol
• Exact Mass: 868.48203620 g/mol
• Topological Polar Surface Area (TPSA): 240.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 16
• H-Bond Donor: 7
• Rotatable Bonds: 9

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	-	0.8792	87.92%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7771	77.71%
OATP2B1 inhibitior	-	0.8752	87.52%
OATP1B1 inhibitior	+	0.8111	81.11%
OATP1B3 inhibitior	+	0.9416	94.16%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7287	72.87%
BSEP inhibitior	+	0.6096	60.96%
P-glycoprotein inhibitior	+	0.7781	77.81%
P-glycoprotein substrate	+	0.5261	52.61%
CYP3A4 substrate	+	0.7433	74.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8835	88.35%
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	+	0.6997	69.97%
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	-	0.9067	90.67%
Skin irritation	-	0.7028	70.28%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7143	71.43%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.6800	68.00%
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	-	0.8847	88.47%
Acute Oral Toxicity (c)	I	0.6455	64.55%
Estrogen receptor binding	+	0.7476	74.76%
Androgen receptor binding	+	0.7449	74.49%
Thyroid receptor binding	-	0.5659	56.59%
Glucocorticoid receptor binding	+	0.7460	74.60%
Aromatase binding	+	0.6940	69.40%
PPAR gamma	+	0.7901	79.01%
Honey bee toxicity	-	0.5995	59.95%
Biodegradation	-	0.7500	75.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.53%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.23%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.57%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.85%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	94.70%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.27%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.87%	96.61%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.69%	91.24%
CHEMBL204	P00734	Thrombin	89.78%	96.01%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.36%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.24%	86.33%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	89.22%	83.57%
CHEMBL259	P32245	Melanocortin receptor 4	88.50%	95.38%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.24%	96.77%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.42%	96.21%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	87.22%	82.50%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.02%	100.00%
CHEMBL2581	P07339	Cathepsin D	86.82%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	85.95%	91.19%
CHEMBL226	P30542	Adenosine A1 receptor	85.60%	95.93%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.16%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.04%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.48%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.74%	92.62%
CHEMBL5255	O00206	Toll-like receptor 4	82.48%	92.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.21%	91.07%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.14%	100.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.11%	94.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.04%	97.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.42%	95.71%
CHEMBL237	P41145	Kappa opioid receptor	81.34%	98.10%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.08%	92.86%

Plants that contains it

• Astragalus lepsensis
• Astragalus melanophrurius
• Astragalus microcephalus
• Astragalus mongholicus
• Astragalus prusianus
• Astragalus trigonus
• Astragalus trimestris

Cross-Links

• PubChem: 11968893
• NPASS: NPC207803
• LOTUS: LTS0042417
• wikiData: Q105147327