[(3S,5S,8R,9R,10S,11R,13R,14R,17S)-3-[(2R,3R,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl] acetate

Details

• Internal ID: 1231019b-a90e-40f0-89bc-853e29e3237e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(3S,5S,8R,9R,10S,11R,13R,14R,17S)-3-[(2R,3R,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2C(CCC2(C3(C1C4(CCC(C(C4CC3)(C)C)OC5C(C(C(C(O5)CO)O)O)OC(=O)C)C)C)C)C6(CCC(O6)C(C)(C)O)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@H](CC[C@]2([C@]3([C@H]1[C@]4(CC[C@@H](C([C@H]4CC3)(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)OC(=O)C)C)C)C)[C@@]6(CC[C@@H](O6)C(C)(C)O)C
• InChI: InChI=1S/C40H66O11/c1-21(42)47-25-19-24-23(40(10)18-14-29(51-40)36(5,6)46)11-16-38(24,8)39(9)17-12-27-35(3,4)28(13-15-37(27,7)33(25)39)50-34-32(48-22(2)43)31(45)30(44)26(20-41)49-34/h23-34,41,44-46H,11-20H2,1-10H3/t23-,24+,25+,26+,27+,28-,29+,30+,31-,32+,33+,34-,37-,38+,39+,40-/m0/s1
• InChI Key: VARDBQBWTSGXRK-OAXIWDCRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₆O₁₁
• Molecular Weight: 722.90 g/mol
• Exact Mass: 722.46051292 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 4.68
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6935	69.35%
Caco-2	-	0.8702	87.02%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8749	87.49%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8108	81.08%
OATP1B3 inhibitior	+	0.9165	91.65%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6787	67.87%
BSEP inhibitior	-	0.7225	72.25%
P-glycoprotein inhibitior	+	0.7882	78.82%
P-glycoprotein substrate	-	0.6542	65.42%
CYP3A4 substrate	+	0.7509	75.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8898	88.98%
CYP3A4 inhibition	-	0.8139	81.39%
CYP2C9 inhibition	-	0.8435	84.35%
CYP2C19 inhibition	-	0.9105	91.05%
CYP2D6 inhibition	-	0.9583	95.83%
CYP1A2 inhibition	-	0.9200	92.00%
CYP2C8 inhibition	+	0.6557	65.57%
CYP inhibitory promiscuity	-	0.9284	92.84%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6499	64.99%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9104	91.04%
Skin irritation	-	0.6889	68.89%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6609	66.09%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.7675	76.75%
skin sensitisation	-	0.9406	94.06%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8386	83.86%
Acute Oral Toxicity (c)	I	0.6269	62.69%
Estrogen receptor binding	+	0.6326	63.26%
Androgen receptor binding	+	0.7225	72.25%
Thyroid receptor binding	-	0.6096	60.96%
Glucocorticoid receptor binding	+	0.6967	69.67%
Aromatase binding	+	0.6999	69.99%
PPAR gamma	+	0.7283	72.83%
Honey bee toxicity	-	0.6283	62.83%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9560	95.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.55%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.15%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.79%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.28%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.90%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.97%	96.77%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.62%	96.21%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.80%	96.61%
CHEMBL259	P32245	Melanocortin receptor 4	88.76%	95.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.66%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	88.24%	89.05%
CHEMBL2996	Q05655	Protein kinase C delta	88.08%	97.79%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	87.91%	95.36%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	86.41%	82.50%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	86.16%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.05%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	85.98%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.81%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.80%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.61%	97.28%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.08%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.72%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.39%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.06%	85.14%
CHEMBL1914	P06276	Butyrylcholinesterase	82.85%	95.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.83%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.95%	92.62%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.80%	96.95%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.76%	97.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.67%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	81.47%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.17%	100.00%
CHEMBL5028	O14672	ADAM10	80.10%	97.50%

Plants that contains it

• Betula ermanii

Cross-Links

• PubChem: 162905243
• LOTUS: LTS0240178
• wikiData: Q105282923