3beta-(beta-D-Glucopyranosyloxy)oleana-12-ene-28-oic acid 2-O-alpha-L-rhamnopyranosyl-6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl ester

Details

• Internal ID: b88dcb0e-6225-4856-b51e-98e1305ff425
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC(=O)C34CCC(CC3C5=CCC6C7(CCC(C(C7CCC6(C5(CC4)C)C)(C)C)OC8C(C(C(C(O8)CO)O)O)O)C)(C)C)COC9C(C(C(CO9)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC(=O)[C@@]34CC[C@@]5(C(=CC[C@H]6[C@]5(CC[C@@H]7[C@@]6(CC[C@@H](C7(C)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)[C@@H]3CC(CC4)(C)C)C)CO[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C53H86O21/c1-23-32(56)36(60)40(64)44(69-23)73-42-38(62)35(59)28(22-68-43-39(63)33(57)26(55)21-67-43)71-46(42)74-47(66)53-17-15-48(2,3)19-25(53)24-9-10-30-50(6)13-12-31(72-45-41(65)37(61)34(58)27(20-54)70-45)49(4,5)29(50)11-14-52(30,8)51(24,7)16-18-53/h9,23,25-46,54-65H,10-22H2,1-8H3/t23-,25-,26+,27+,28+,29-,30+,31-,32-,33-,34+,35+,36+,37-,38-,39+,40+,41+,42+,43-,44-,45-,46-,50-,51+,52+,53-/m0/s1
• InChI Key: BAPQSGOZUURXBD-MLXUCUEZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₆O₂₁
• Molecular Weight: 1059.20 g/mol
• Exact Mass: 1058.56615975 g/mol
• Topological Polar Surface Area (TPSA): 334.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.37
• H-Bond Acceptor: 21
• 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	+	0.7891	78.91%
Caco-2	-	0.8873	88.73%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7752	77.52%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8513	85.13%
P-glycoprotein inhibitior	+	0.7509	75.09%
P-glycoprotein substrate	-	0.6706	67.06%
CYP3A4 substrate	+	0.7338	73.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.7039	70.39%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9028	90.28%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7470	74.70%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.9384	93.84%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7848	78.48%
Androgen receptor binding	+	0.7310	73.10%
Thyroid receptor binding	+	0.5234	52.34%
Glucocorticoid receptor binding	+	0.7621	76.21%
Aromatase binding	+	0.6344	63.44%
PPAR gamma	+	0.8094	80.94%
Honey bee toxicity	-	0.6562	65.62%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.9411	94.11%

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	99.04%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.52%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.06%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.12%	97.36%
CHEMBL2581	P07339	Cathepsin D	91.65%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.18%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.92%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.91%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.86%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.74%	95.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.14%	86.92%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.97%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.87%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.94%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.81%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	84.76%	95.93%
CHEMBL5255	O00206	Toll-like receptor 4	83.65%	92.50%
CHEMBL5028	O14672	ADAM10	83.51%	97.50%

Plants that contains it

• Acacia aulacocarpa
• Anemonastrum flaccidum
• Ardisia neriifolia
• Aspidosperma subincanum
• Cryptocarya aschersoniana
• Eupatorium argentinum
• Garcinia madruno
• Guatteria ucayalina
• Juniperus brevifolia
• Lonicera japonica
• Peritassa compta
• Psiadia dentata

Cross-Links

• PubChem: 101447522
• NPASS: NPC16797