(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-2-[[(1S,2S,4S,5R,8R,9R,10S,13S,14R,17S,18R,20R)-2-hydroxy-9,20-bis(hydroxymethyl)-4,5,9,13,20-pentamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 09e38e6e-7bbb-4268-94ed-d5d2729e9e8a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-2-[[(1S,2S,4S,5R,8R,9R,10S,13S,14R,17S,18R,20R)-2-hydroxy-9,20-bis(hydroxymethyl)-4,5,9,13,20-pentamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2(C)CO)CCC4(C3C=CC56C4(CC(C7(C5CC(CC7)(C)CO)CO6)O)C)C)C)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)CO)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]([C@]2(C)CO)CC[C@@]4([C@@H]3C=C[C@@]56[C@]4(C[C@@H]([C@@]7([C@H]5C[C@](CC7)(C)CO)CO6)O)C)C)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O
• InChI: InChI=1S/C48H78O19/c1-22-30(54)37(66-39-35(59)33(57)31(55)23(17-49)63-39)38(67-40-36(60)34(58)32(56)24(18-50)64-40)41(62-22)65-29-9-10-43(3)25(44(29,4)20-52)7-11-45(5)26(43)8-12-48-27-15-42(2,19-51)13-14-47(27,21-61-48)28(53)16-46(45,48)6/h8,12,22-41,49-60H,7,9-11,13-21H2,1-6H3/t22-,23-,24-,25-,26-,27-,28+,29+,30+,31-,32-,33+,34+,35-,36-,37+,38-,39+,40+,41+,42-,43+,44+,45-,46+,47-,48+/m1/s1
• InChI Key: CJWYMLSZAMZYPC-XPALOFSASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₈O₁₉
• Molecular Weight: 959.10 g/mol
• Exact Mass: 958.51373025 g/mol
• Topological Polar Surface Area (TPSA): 307.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.43
• H-Bond Acceptor: 19
• H-Bond Donor: 12
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5788	57.88%
Caco-2	-	0.8842	88.42%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6011	60.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8500	85.00%
OATP1B3 inhibitior	+	0.9380	93.80%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.6248	62.48%
P-glycoprotein inhibitior	+	0.7514	75.14%
P-glycoprotein substrate	+	0.5562	55.62%
CYP3A4 substrate	+	0.7334	73.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8287	82.87%
CYP3A4 inhibition	-	0.9502	95.02%
CYP2C9 inhibition	-	0.9048	90.48%
CYP2C19 inhibition	-	0.8767	87.67%
CYP2D6 inhibition	-	0.9511	95.11%
CYP1A2 inhibition	-	0.9104	91.04%
CYP2C8 inhibition	+	0.7155	71.55%
CYP inhibitory promiscuity	-	0.9498	94.98%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6234	62.34%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9052	90.52%
Skin irritation	-	0.6247	62.47%
Skin corrosion	-	0.9466	94.66%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7478	74.78%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.5689	56.89%
skin sensitisation	-	0.9266	92.66%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6026	60.26%
Acute Oral Toxicity (c)	I	0.7917	79.17%
Estrogen receptor binding	+	0.7604	76.04%
Androgen receptor binding	+	0.7576	75.76%
Thyroid receptor binding	-	0.5538	55.38%
Glucocorticoid receptor binding	+	0.6213	62.13%
Aromatase binding	+	0.6451	64.51%
PPAR gamma	+	0.7507	75.07%
Honey bee toxicity	-	0.6344	63.44%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8868	88.68%

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	97.03%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.53%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.13%	97.36%
CHEMBL226	P30542	Adenosine A1 receptor	94.53%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.28%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.51%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.15%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.22%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.13%	86.33%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	85.53%	97.47%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.76%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.22%	89.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.78%	91.24%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.68%	97.53%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.58%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.40%	95.89%
CHEMBL2581	P07339	Cathepsin D	81.61%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.52%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.42%	100.00%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	80.75%	85.83%
CHEMBL259	P32245	Melanocortin receptor 4	80.26%	95.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.25%	92.62%

Plants that contains it

• Bupleurum rigidum

Cross-Links

• PubChem: 21609768
• LOTUS: LTS0041363
• wikiData: Q104961796