(2S,3R,4S,5R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-[[(1S,2R,4S,5R,8R,10S,13S,14R,18R,19S,20R)-2-hydroxy-4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol

Details

• Internal ID: 522cf2f5-9221-41bf-a519-a5cca78dd677
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4S,5R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-[[(1S,2R,4S,5R,8R,10S,13S,14R,18R,19S,20R)-2-hydroxy-4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
• SMILES (Canonical): CC1CCC23COC4(C2C1C)C=CC5C6(CCC(C(C6CCC5(C4(CC3O)C)C)(C)C)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(CO9)O)O)O)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]23COC4([C@@H]2[C@H]1C)C=C[C@@H]5[C@]6(CC[C@@H](C([C@@H]6CC[C@]5([C@@]4(C[C@H]3O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)C
• InChI: InChI=1S/C47H76O17/c1-21-8-14-46-20-59-47(38(46)22(21)2)15-10-27-43(5)12-11-29(42(3,4)26(43)9-13-44(27,6)45(47,7)16-28(46)51)62-40-36(33(55)31(53)24(17-48)60-40)64-41-37(34(56)32(54)25(18-49)61-41)63-39-35(57)30(52)23(50)19-58-39/h10,15,21-41,48-57H,8-9,11-14,16-20H2,1-7H3/t21-,22+,23-,24-,25-,26+,27-,28-,29+,30+,31+,32-,33+,34+,35-,36-,37-,38-,39+,40+,41+,43+,44-,45+,46+,47?/m1/s1
• InChI Key: OERYSJKYOLNHAD-MCHLQZTNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₆O₁₇
• Molecular Weight: 913.10 g/mol
• Exact Mass: 912.50825095 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 0.10
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6441	64.41%
Caco-2	-	0.8902	89.02%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6663	66.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7993	79.93%
OATP1B3 inhibitior	+	0.9158	91.58%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.4623	46.23%
P-glycoprotein inhibitior	+	0.7494	74.94%
P-glycoprotein substrate	+	0.5262	52.62%
CYP3A4 substrate	+	0.7397	73.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8287	82.87%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.8634	86.34%
CYP2C19 inhibition	-	0.8659	86.59%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9115	91.15%
CYP2C8 inhibition	+	0.6932	69.32%
CYP inhibitory promiscuity	-	0.9473	94.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6210	62.10%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9060	90.60%
Skin irritation	-	0.6612	66.12%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7674	76.74%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.7706	77.06%
skin sensitisation	-	0.9108	91.08%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.9126	91.26%
Acute Oral Toxicity (c)	I	0.7129	71.29%
Estrogen receptor binding	+	0.7784	77.84%
Androgen receptor binding	+	0.7556	75.56%
Thyroid receptor binding	-	0.5672	56.72%
Glucocorticoid receptor binding	+	0.6457	64.57%
Aromatase binding	+	0.6570	65.70%
PPAR gamma	+	0.7660	76.60%
Honey bee toxicity	-	0.6333	63.33%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9152	91.52%

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	98.33%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.28%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.74%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.76%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.13%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.81%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.08%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.48%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.99%	96.61%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.58%	97.36%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.37%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.81%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.26%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.23%	97.25%
CHEMBL1951	P21397	Monoamine oxidase A	84.11%	91.49%
CHEMBL5255	O00206	Toll-like receptor 4	82.35%	92.50%
CHEMBL325	Q13547	Histone deacetylase 1	82.26%	95.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.81%	94.45%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.47%	97.28%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.42%	91.24%
CHEMBL259	P32245	Melanocortin receptor 4	81.14%	95.38%
CHEMBL2243	O00519	Anandamide amidohydrolase	81.12%	97.53%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.36%	97.14%

Plants that contains it

• Bupleurum rotundifolium

Cross-Links

• PubChem: 163194326
• LOTUS: LTS0062677
• wikiData: Q105190492