[(3S,4S,5S,6R)-4-acetyloxy-5-hydroxy-6-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-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-3-yl] acetate

Details

• Internal ID: de40c270-7c47-4b84-9264-43b437fca8fd
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(3S,4S,5S,6R)-4-acetyloxy-5-hydroxy-6-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-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-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1COC(C(C1OC(=O)C)O)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
• SMILES (Isomeric): CC(=O)O[C@H]1CO[C@@H]([C@H]([C@@H]1OC(=O)C)O)O[C@H]2CC[C@]34C[C@]35CC[C@@]6([C@H]([C@H](C[C@]6([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)C)O)[C@]8(CC[C@H](O8)C(C)(C)O)C)C
• InChI: InChI=1S/C45H72O16/c1-21(47)56-26-19-55-37(33(53)34(26)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)16-24(36(45)39(28,3)4)58-38-32(52)31(51)30(50)25(18-46)59-38/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+/m0/s1
• InChI Key: LRWUZSAOXSUTCO-NVOXUARWSA-N
• Popularity: 1 reference 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	-	0.8787	87.87%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7771	77.71%
OATP2B1 inhibitior	-	0.8765	87.65%
OATP1B1 inhibitior	+	0.8123	81.23%
OATP1B3 inhibitior	+	0.9416	94.16%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7287	72.87%
BSEP inhibitior	+	0.6846	68.46%
P-glycoprotein inhibitior	+	0.7787	77.87%
P-glycoprotein substrate	+	0.5565	55.65%
CYP3A4 substrate	+	0.7459	74.59%
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	+	0.7110	71.10%
CYP inhibitory promiscuity	-	0.9558	95.58%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6430	64.30%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9065	90.65%
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	+	0.6969	69.69%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.6800	68.00%
skin sensitisation	-	0.9164	91.64%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.9297	92.97%
Acute Oral Toxicity (c)	I	0.6455	64.55%
Estrogen receptor binding	+	0.7679	76.79%
Androgen receptor binding	+	0.7437	74.37%
Thyroid receptor binding	-	0.5525	55.25%
Glucocorticoid receptor binding	+	0.7547	75.47%
Aromatase binding	+	0.6749	67.49%
PPAR gamma	+	0.7853	78.53%
Honey bee toxicity	-	0.5986	59.86%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
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	98.93%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.14%	97.25%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	96.03%	83.57%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.57%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	94.83%	96.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.14%	96.61%
CHEMBL220	P22303	Acetylcholinesterase	93.87%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.99%	96.09%
CHEMBL204	P00734	Thrombin	92.22%	96.01%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.90%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.63%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.44%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.26%	85.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.04%	91.24%
CHEMBL259	P32245	Melanocortin receptor 4	88.42%	95.38%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	88.38%	82.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.97%	86.33%
CHEMBL2581	P07339	Cathepsin D	87.18%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.71%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.46%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.75%	91.07%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.95%	95.50%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.85%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.44%	92.50%
CHEMBL226	P30542	Adenosine A1 receptor	83.33%	95.93%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.24%	92.62%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.06%	98.75%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.89%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.19%	91.19%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.93%	89.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.57%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.13%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.61%	97.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.16%	95.71%

Plants that contains it

• Astragalus spinosus

Cross-Links

• PubChem: 162895071
• LOTUS: LTS0272203
• wikiData: Q105156363