[(2S,3R,4S,5R)-3-acetyloxy-5-hydroxy-2-[[(1S,3R,6S,8R,9S,11S,12S,15S,16S)-15-hydroxy-15-[(2R,5S)-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: 22f546f6-6dc2-4bb0-8b25-280c8c1e3667
• 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-[[(1S,3R,6S,8R,9S,11S,12S,15S,16S)-15-hydroxy-15-[(2R,5S)-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(C5CC(C4C2(C)C)OC7C(C(C(C(O7)CO)O)O)O)(CCC6(C8(CCC(O8)C(C)(C)O)C)O)C)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@]34C[C@]35CC[C@]6([C@]([C@@H]5C[C@@H]([C@H]4C2(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)(CC[C@]6([C@]8(CC[C@H](O8)C(C)(C)O)C)O)C)C)O
• InChI: InChI=1S/C45H72O16/c1-22(47)56-33-24(49)20-55-37(34(33)57-23(2)48)60-28-11-13-44-21-43(44)16-15-41(8)40(7,14-17-45(41,54)42(9)12-10-29(61-42)39(5,6)53)27(43)18-25(35(44)38(28,3)4)58-36-32(52)31(51)30(50)26(19-46)59-36/h24-37,46,49-54H,10-21H2,1-9H3/t24-,25+,26-,27+,28+,29+,30-,31+,32-,33+,34-,35+,36-,37+,40+,41+,42-,43+,44-,45+/m1/s1
• InChI Key: LAWPHHZXTUPSDG-IWJFZPFQSA-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: 2.10
• Atomic LogP (AlogP): 2.01
• 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	-	0.8756	87.56%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7771	77.71%
OATP2B1 inhibitior	-	0.8748	87.48%
OATP1B1 inhibitior	+	0.7991	79.91%
OATP1B3 inhibitior	+	0.9416	94.16%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7287	72.87%
BSEP inhibitior	+	0.6092	60.92%
P-glycoprotein inhibitior	+	0.7734	77.34%
P-glycoprotein substrate	+	0.5836	58.36%
CYP3A4 substrate	+	0.7474	74.74%
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	+	0.7125	71.25%
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	-	0.9048	90.48%
Skin irritation	-	0.7028	70.28%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7271	72.71%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.6550	65.50%
skin sensitisation	-	0.9164	91.64%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8107	81.07%
Acute Oral Toxicity (c)	I	0.6455	64.55%
Estrogen receptor binding	+	0.7373	73.73%
Androgen receptor binding	+	0.7530	75.30%
Thyroid receptor binding	-	0.5549	55.49%
Glucocorticoid receptor binding	+	0.7343	73.43%
Aromatase binding	+	0.6823	68.23%
PPAR gamma	+	0.7923	79.23%
Honey bee toxicity	-	0.6103	61.03%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
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	98.83%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.02%	96.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	93.03%	91.24%
CHEMBL259	P32245	Melanocortin receptor 4	92.41%	95.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.20%	97.09%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	91.15%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.52%	94.45%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	88.92%	82.50%
CHEMBL2581	P07339	Cathepsin D	88.47%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.17%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.93%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.77%	85.14%
CHEMBL5255	O00206	Toll-like receptor 4	86.62%	92.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.34%	95.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.98%	96.95%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.27%	83.57%
CHEMBL220	P22303	Acetylcholinesterase	85.15%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.58%	91.07%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.01%	95.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.81%	96.21%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	83.15%	92.86%
CHEMBL226	P30542	Adenosine A1 receptor	83.05%	95.93%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.00%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.94%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.90%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.89%	95.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.53%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.96%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.95%	89.50%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.62%	91.03%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.44%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.26%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.16%	93.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.89%	92.94%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.82%	92.62%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.17%	96.61%

Plants that contains it

• Astragalus trigonus

Cross-Links

• PubChem: 163070394
• LOTUS: LTS0013152
• wikiData: Q105149034