(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,9R,10S,13S,14R,17S,18R)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-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: 97a53ff9-c7da-4e15-bc16-dac7ad3dbb98
• 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,9R,10S,13S,14R,17S,18R)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-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)CO)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]([C@]2(C)CO)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/C47H76O17/c1-22-30(52)33(55)36(64-40-37(34(56)32(54)24(18-48)61-40)63-38-35(57)31(53)23(50)19-58-38)39(60-22)62-29-10-11-42(4)25(43(29,5)20-49)8-12-44(6)26(42)9-13-47-27-16-41(2,3)14-15-46(27,21-59-47)28(51)17-45(44,47)7/h9,13,22-40,48-57H,8,10-12,14-21H2,1-7H3/t22-,23-,24-,25-,26-,27-,28-,29+,30+,31+,32-,33+,34+,35-,36-,37-,38+,39+,40+,42+,43+,44-,45+,46-,47+/m1/s1
• InChI Key: ZHSIBPZKCLOKSN-PQYGZLOGSA-N
• Popularity: 2 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: 1.00
• Atomic LogP (AlogP): 0.24
• 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	-	0.8881	88.81%
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	+	0.8302	83.02%
OATP1B3 inhibitior	+	0.9158	91.58%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.7318	73.18%
P-glycoprotein inhibitior	+	0.7477	74.77%
P-glycoprotein substrate	+	0.5796	57.96%
CYP3A4 substrate	+	0.7350	73.50%
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	+	0.7046	70.46%
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	-	0.9051	90.51%
Skin irritation	-	0.6612	66.12%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7540	75.40%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6386	63.86%
skin sensitisation	-	0.9108	91.08%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8637	86.37%
Acute Oral Toxicity (c)	I	0.7129	71.29%
Estrogen receptor binding	+	0.7659	76.59%
Androgen receptor binding	+	0.7541	75.41%
Thyroid receptor binding	-	0.5463	54.63%
Glucocorticoid receptor binding	+	0.6527	65.27%
Aromatase binding	+	0.6602	66.02%
PPAR gamma	+	0.7611	76.11%
Honey bee toxicity	-	0.6433	64.33%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
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	97.99%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	97.25%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.90%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.48%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.56%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.34%	94.45%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.74%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.52%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.27%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.88%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.40%	92.94%
CHEMBL2243	O00519	Anandamide amidohydrolase	87.34%	97.53%
CHEMBL1914	P06276	Butyrylcholinesterase	86.72%	95.00%
CHEMBL1937	Q92769	Histone deacetylase 2	86.46%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.51%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	84.93%	91.49%
CHEMBL2581	P07339	Cathepsin D	84.78%	98.95%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	84.51%	92.78%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	84.47%	97.86%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.87%	94.00%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	82.84%	85.83%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.75%	92.88%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.67%	86.92%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.50%	91.24%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.49%	91.07%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	81.13%	97.47%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	80.55%	98.99%
CHEMBL325	Q13547	Histone deacetylase 1	80.53%	95.92%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.52%	97.25%
CHEMBL233	P35372	Mu opioid receptor	80.19%	97.93%

Plants that contains it

• Bupleurum rotundifolium

Cross-Links

• PubChem: 16097913
• LOTUS: LTS0257352
• wikiData: Q105375972