(2S,3R,4R,5S)-2-[(2S,3S,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-2-[[(1R,2R,4S,5R,8R,10R,13S,14S,17R,18R)-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-6-methyloxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol

Details

• Internal ID: 077e0d4e-ce28-4f45-8ee9-71b48c75489d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4R,5S)-2-[(2S,3S,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-2-[[(1R,2R,4S,5R,8R,10R,13S,14S,17R,18R)-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-6-methyloxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2(C)C)CCC4(C3C=CC56C4(CC(C7(C5CC(CC7)(C)C)CO6)O)C)C)C)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(CO9)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]4([C@H]3C=C[C@]56[C@]4(C[C@H]([C@]7([C@H]5CC(CC7)(C)C)CO6)O)C)C)C)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)O)O
• InChI: InChI=1S/C47H76O16/c1-22-30(51)33(54)36(63-40-37(34(55)32(53)24(19-48)60-40)62-38-35(56)31(52)23(49)20-57-38)39(59-22)61-29-11-12-43(6)25(42(29,4)5)9-13-44(7)26(43)10-14-47-27-17-41(2,3)15-16-46(27,21-58-47)28(50)18-45(44,47)8/h10,14,22-40,48-56H,9,11-13,15-21H2,1-8H3/t22-,23+,24-,25+,26+,27-,28-,29-,30-,31-,32+,33-,34-,35-,36-,37+,38+,39+,40+,43+,44-,45+,46+,47-/m1/s1
• InChI Key: LOMHITWHYXGWQO-QCBBZXMQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₆O₁₆
• Molecular Weight: 897.10 g/mol
• Exact Mass: 896.51333633 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.27
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6441	64.41%
Caco-2	-	0.8870	88.70%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6663	66.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7803	78.03%
OATP1B3 inhibitior	+	0.9158	91.58%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.6499	64.99%
P-glycoprotein inhibitior	+	0.7514	75.14%
P-glycoprotein substrate	+	0.5173	51.73%
CYP3A4 substrate	+	0.7325	73.25%
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	+	0.6876	68.76%
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	-	0.9058	90.58%
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	+	0.7553	75.53%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.7511	75.11%
skin sensitisation	-	0.9108	91.08%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.9406	94.06%
Acute Oral Toxicity (c)	I	0.7129	71.29%
Estrogen receptor binding	+	0.7641	76.41%
Androgen receptor binding	+	0.7496	74.96%
Thyroid receptor binding	-	0.5558	55.58%
Glucocorticoid receptor binding	+	0.6747	67.47%
Aromatase binding	+	0.6684	66.84%
PPAR gamma	+	0.7641	76.41%
Honey bee toxicity	-	0.6216	62.16%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.51%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	98.19%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.72%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.19%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.54%	97.09%
CHEMBL1914	P06276	Butyrylcholinesterase	90.79%	95.00%
CHEMBL2581	P07339	Cathepsin D	90.79%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.97%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.80%	94.45%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.58%	95.50%
CHEMBL1951	P21397	Monoamine oxidase A	88.38%	91.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.96%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.68%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.04%	95.89%
CHEMBL2243	O00519	Anandamide amidohydrolase	83.87%	97.53%
CHEMBL1937	Q92769	Histone deacetylase 2	83.20%	94.75%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.85%	92.88%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	82.46%	96.11%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.28%	91.24%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.25%	89.00%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	81.05%	97.86%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.03%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.43%	86.92%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.17%	96.61%

Plants that contains it

• Bupleurum rotundifolium

Cross-Links

• PubChem: 162993620
• LOTUS: LTS0086535
• wikiData: Q105154794