[(2S,3R,4S,5R)-3-acetyloxy-5-hydroxy-2-[[(3S,5R,6S,8R,9R,10S,13R,14S,16S,17R)-16-hydroxy-17-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,9,10,13,14-hexamethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,5,6,7,8,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-4-yl] acetate

Details

• Internal ID: 113b642a-3d8c-41e2-a8ac-27a866110f25
• 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-[[(3S,5R,6S,8R,9R,10S,13R,14S,16S,17R)-16-hydroxy-17-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,9,10,13,14-hexamethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,5,6,7,8,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-4-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(COC(C1OC(=O)C)OC2CCC3(C(C2(C)C)C(CC4C3(CCC5(C4(CC(C5C6(CCC(O6)C(C)(C)O)C)O)C)C)C)OC7C(C(C(C(O7)CO)O)O)O)C)O
• SMILES (Isomeric): CC(=O)O[C@H]1[C@@H](CO[C@H]([C@@H]1OC(=O)C)O[C@H]2CC[C@]3([C@H](C2(C)C)[C@H](C[C@@H]4[C@]3(CC[C@]5([C@]4(C[C@@H]([C@@H]5[C@]6(CC[C@H](O6)C(C)(C)O)C)O)C)C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)O
• InChI: InChI=1S/C46H76O16/c1-22(48)57-34-25(51)21-56-39(35(34)58-23(2)49)61-29-12-14-43(8)37(40(29,3)4)26(59-38-33(54)32(53)31(52)27(20-47)60-38)18-28-42(43,7)16-17-44(9)36(24(50)19-45(28,44)10)46(11)15-13-30(62-46)41(5,6)55/h24-39,47,50-55H,12-21H2,1-11H3/t24-,25+,26-,27+,28+,29-,30-,31+,32-,33+,34-,35+,36-,37-,38+,39-,42+,43-,44+,45-,46+/m0/s1
• InChI Key: LPDRYJZGRMHSIY-YEQOTKHTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₇₆O₁₆
• Molecular Weight: 885.10 g/mol
• Exact Mass: 884.51333633 g/mol
• Topological Polar Surface Area (TPSA): 240.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.50
• 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	+	0.6843	68.43%
Caco-2	-	0.8777	87.77%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8306	83.06%
OATP2B1 inhibitior	-	0.8774	87.74%
OATP1B1 inhibitior	+	0.8202	82.02%
OATP1B3 inhibitior	+	0.9361	93.61%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7037	70.37%
BSEP inhibitior	+	0.6907	69.07%
P-glycoprotein inhibitior	+	0.7788	77.88%
P-glycoprotein substrate	-	0.5265	52.65%
CYP3A4 substrate	+	0.7470	74.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8898	88.98%
CYP3A4 inhibition	-	0.8045	80.45%
CYP2C9 inhibition	-	0.8759	87.59%
CYP2C19 inhibition	-	0.9024	90.24%
CYP2D6 inhibition	-	0.9558	95.58%
CYP1A2 inhibition	-	0.9368	93.68%
CYP2C8 inhibition	+	0.6763	67.63%
CYP inhibitory promiscuity	-	0.9654	96.54%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6247	62.47%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9050	90.50%
Skin irritation	-	0.6827	68.27%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.5870	58.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7106	71.06%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.6634	66.34%
skin sensitisation	-	0.9363	93.63%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.7831	78.31%
Acute Oral Toxicity (c)	I	0.7247	72.47%
Estrogen receptor binding	+	0.7457	74.57%
Androgen receptor binding	+	0.7304	73.04%
Thyroid receptor binding	-	0.5540	55.40%
Glucocorticoid receptor binding	+	0.7628	76.28%
Aromatase binding	+	0.6911	69.11%
PPAR gamma	+	0.7950	79.50%
Honey bee toxicity	-	0.5937	59.37%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9205	92.05%

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	97.31%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.76%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.41%	97.25%
CHEMBL1914	P06276	Butyrylcholinesterase	95.01%	95.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.41%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.56%	96.61%
CHEMBL259	P32245	Melanocortin receptor 4	91.81%	95.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.79%	97.09%
CHEMBL220	P22303	Acetylcholinesterase	91.40%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.18%	91.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.95%	86.33%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	88.01%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.06%	97.28%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.96%	95.50%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	85.89%	82.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.73%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.66%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.23%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	83.96%	92.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.90%	92.62%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.69%	96.21%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.57%	91.07%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.24%	96.77%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	83.12%	95.36%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.06%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.67%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	82.60%	91.19%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.34%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.17%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.47%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.27%	95.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.13%	94.00%

Plants that contains it

• Astragalus sieversianus

Cross-Links

• PubChem: 162978009
• LOTUS: LTS0020971
• wikiData: Q105155120