beta-D-Glucopyranosyl (3beta,4alpha)-23-hydroxy-3-[(O-beta-D-ribopyranosyl-(1-->3)-O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]olean-12-en-28-oate

Details

• Internal ID: f359e2b6-b4f4-4c0b-a74b-89a06d890230
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-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(COC2OC3CCC4(C(C3(C)CO)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)OC8C(C(C(C(O8)CO)O)O)O)C)C)C)O)O)O)OC9C(C(C(CO9)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](CO[C@H]2O[C@H]3CC[C@]4([C@H]([C@]3(C)CO)CC[C@@]5([C@@H]4CC=C6[C@]5(CC[C@@]7([C@H]6CC(CC7)(C)C)C(=O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)C)O)O)O)O[C@H]9[C@@H]([C@@H]([C@@H](CO9)O)O)O)O
• InChI: InChI=1S/C52H84O21/c1-23-32(57)40(71-42-37(62)33(58)26(55)20-66-42)39(64)44(68-23)72-41-34(59)27(56)21-67-45(41)70-31-11-12-48(4)29(49(31,5)22-54)10-13-51(7)30(48)9-8-24-25-18-47(2,3)14-16-52(25,17-15-50(24,51)6)46(65)73-43-38(63)36(61)35(60)28(19-53)69-43/h8,23,25-45,53-64H,9-22H2,1-7H3/t23-,25-,26+,27-,28+,29+,30+,31-,32-,33+,34-,35+,36-,37+,38+,39+,40+,41+,42-,43-,44-,45-,48-,49-,50+,51+,52-/m0/s1
• InChI Key: YDXWQWMRQORSTI-WKTUCKCCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₄O₂₁
• Molecular Weight: 1045.20 g/mol
• Exact Mass: 1044.55050968 g/mol
• Topological Polar Surface Area (TPSA): 334.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.76
• H-Bond Acceptor: 21
• H-Bond Donor: 12
• Rotatable Bonds: 10

Synonyms

• 172671-38-4
• beta-D-Glucopyranosyl (3beta,4alpha)-23-hydroxy-3-[(O-beta-D-ribopyranosyl-(1-->3)-O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]olean-12-en-28-oate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8862	88.62%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8527	85.27%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8622	86.22%
P-glycoprotein inhibitior	+	0.7471	74.71%
P-glycoprotein substrate	-	0.5836	58.36%
CYP3A4 substrate	+	0.7349	73.49%
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	+	0.7154	71.54%
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	-	0.9026	90.26%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7727	77.27%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8461	84.61%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.8041	80.41%
Androgen receptor binding	+	0.7376	73.76%
Thyroid receptor binding	+	0.5460	54.60%
Glucocorticoid receptor binding	+	0.7593	75.93%
Aromatase binding	+	0.6846	68.46%
PPAR gamma	+	0.8234	82.34%
Honey bee toxicity	-	0.6871	68.71%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5550	55.50%
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	98.17%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.73%	97.36%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	94.77%	95.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.56%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.15%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.70%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.05%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.42%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.81%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.75%	86.92%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.31%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.12%	96.77%
CHEMBL2581	P07339	Cathepsin D	84.11%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.39%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.08%	91.07%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.74%	94.33%
CHEMBL5028	O14672	ADAM10	80.73%	97.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.39%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.06%	95.89%

Plants that contains it

• Clematis stans
• Clematis vitalba

Cross-Links

• PubChem: 10629908
• LOTUS: LTS0239031
• wikiData: Q105347093