[(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-3,5-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-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] acetate

Details

• Internal ID: d29a4f20-506a-4f74-b2b4-18c9a2eea261
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-3,5-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-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] acetate
• 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)O)OC8C(C(C(C(O8)CO)O)OC(=O)C)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)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)OC(=O)C)O)O
• InChI: InChI=1S/C44H70O14/c1-22-30(49)34(58-37-33(52)35(55-23(2)47)31(50)24(19-45)56-37)32(51)36(54-22)57-29-11-12-39(5)25(40(29,6)20-46)9-13-41(7)26(39)10-14-44-27-17-38(3,4)15-16-43(27,21-53-44)28(48)18-42(41,44)8/h10,14,22,24-37,45-46,48-52H,9,11-13,15-21H2,1-8H3/t22-,24-,25-,26-,27-,28-,29+,30+,31-,32-,33-,34+,35+,36+,37+,39+,40+,41-,42+,43-,44+/m1/s1
• InChI Key: HAUJZZHHHIUYEJ-IWHJBOPKSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₇₀O₁₄
• Molecular Weight: 823.00 g/mol
• Exact Mass: 822.47655690 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.35
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8427	84.27%
Caco-2	-	0.8802	88.02%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7365	73.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8192	81.92%
OATP1B3 inhibitior	+	0.9043	90.43%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.6100	61.00%
P-glycoprotein inhibitior	+	0.7590	75.90%
P-glycoprotein substrate	+	0.5606	56.06%
CYP3A4 substrate	+	0.7365	73.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8775	87.75%
CYP3A4 inhibition	-	0.8925	89.25%
CYP2C9 inhibition	-	0.8473	84.73%
CYP2C19 inhibition	-	0.8648	86.48%
CYP2D6 inhibition	-	0.9487	94.87%
CYP1A2 inhibition	-	0.9256	92.56%
CYP2C8 inhibition	+	0.6853	68.53%
CYP inhibitory promiscuity	-	0.9247	92.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6153	61.53%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9072	90.72%
Skin irritation	-	0.6287	62.87%
Skin corrosion	-	0.9447	94.47%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7276	72.76%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.5613	56.13%
skin sensitisation	-	0.9148	91.48%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.5579	55.79%
Acute Oral Toxicity (c)	I	0.6563	65.63%
Estrogen receptor binding	+	0.7718	77.18%
Androgen receptor binding	+	0.7547	75.47%
Thyroid receptor binding	-	0.5464	54.64%
Glucocorticoid receptor binding	+	0.6892	68.92%
Aromatase binding	+	0.6673	66.73%
PPAR gamma	+	0.7694	76.94%
Honey bee toxicity	-	0.6606	66.06%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9336	93.36%

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	97.24%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.90%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.46%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	92.79%	95.93%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.57%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.10%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.32%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.68%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.34%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.19%	95.89%
CHEMBL2581	P07339	Cathepsin D	86.66%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.59%	95.50%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	85.33%	97.47%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.72%	91.07%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.07%	91.24%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.93%	86.92%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.29%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.55%	94.33%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.49%	96.38%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.41%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.36%	92.62%
CHEMBL5028	O14672	ADAM10	82.06%	97.50%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	81.66%	92.78%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	81.48%	98.99%
CHEMBL5255	O00206	Toll-like receptor 4	80.80%	92.50%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.61%	81.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.41%	93.04%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	80.07%	97.86%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.05%	89.50%

Plants that contains it

• Bupleurum chinense
• Bupleurum falcatum
• Bupleurum kunmingense
• Bupleurum marginatum
• Bupleurum polyclonum
• Bupleurum scorzonerifolium

Cross-Links

• PubChem: 21637628
• NPASS: NPC208708
• LOTUS: LTS0215679
• wikiData: Q104402592