6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl (2alpha,3beta,4alpha,6beta)-2,3,6,23-tetrahydroxyurs-12-en-28-oate

Details

• Internal ID: e2cbdd3f-97a8-405e-99db-6f27b28b53f3
• 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-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (1S,2R,4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
• SMILES (Canonical): CC1CCC2(CCC3(C(=CCC4C3(CC(C5C4(CC(C(C5(C)CO)O)O)C)O)C)C2C1C)C)C(=O)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(C[C@H]([C@@H]5[C@@]4(C[C@H]([C@@H]([C@@]5(C)CO)O)O)C)O)C)[C@@H]2[C@H]1C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O
• InChI: InChI=1S/C42H68O16/c1-18-9-10-42(37(54)58-36-32(52)30(50)28(48)24(57-36)16-55-35-31(51)29(49)27(47)23(15-43)56-35)12-11-40(5)20(26(42)19(18)2)7-8-25-38(3)13-22(46)34(53)39(4,17-44)33(38)21(45)14-41(25,40)6/h7,18-19,21-36,43-53H,8-17H2,1-6H3/t18-,19+,21-,22-,23-,24-,25-,26+,27-,28-,29+,30+,31-,32-,33-,34+,35-,36+,38-,39+,40-,41-,42+/m1/s1
• InChI Key: JSQCMNXZFPMWES-WRBXKWMASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₈O₁₆
• Molecular Weight: 829.00 g/mol
• Exact Mass: 828.45073608 g/mol
• Topological Polar Surface Area (TPSA): 277.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.91
• H-Bond Acceptor: 16
• H-Bond Donor: 11
• Rotatable Bonds: 7

Synonyms

• 386223-75-2
• 6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl (2alpha,3beta,4alpha,6beta)-2,3,6,23-tetrahydroxyurs-12-en-28-oate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7336	73.36%
Caco-2	-	0.8891	88.91%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8246	82.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8864	88.64%
OATP1B3 inhibitior	-	0.4366	43.66%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	-	0.4705	47.05%
P-glycoprotein inhibitior	+	0.7300	73.00%
P-glycoprotein substrate	-	0.5322	53.22%
CYP3A4 substrate	+	0.7186	71.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9357	93.57%
CYP2C9 inhibition	-	0.9347	93.47%
CYP2C19 inhibition	-	0.9271	92.71%
CYP2D6 inhibition	-	0.9492	94.92%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	+	0.7139	71.39%
CYP inhibitory promiscuity	-	0.9709	97.09%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6290	62.90%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9112	91.12%
Skin irritation	-	0.5531	55.31%
Skin corrosion	-	0.9498	94.98%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7086	70.86%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9157	91.57%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.6774	67.74%
Acute Oral Toxicity (c)	III	0.6947	69.47%
Estrogen receptor binding	+	0.7807	78.07%
Androgen receptor binding	+	0.7548	75.48%
Thyroid receptor binding	-	0.5978	59.78%
Glucocorticoid receptor binding	+	0.6538	65.38%
Aromatase binding	+	0.6406	64.06%
PPAR gamma	+	0.7552	75.52%
Honey bee toxicity	-	0.7151	71.51%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6350	63.50%
Fish aquatic toxicity	+	0.9206	92.06%

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	99.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.15%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.72%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.68%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	91.20%	95.93%
CHEMBL2581	P07339	Cathepsin D	90.29%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.79%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.47%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.28%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.84%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.55%	86.92%
CHEMBL5255	O00206	Toll-like receptor 4	85.48%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.50%	95.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.95%	96.77%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.59%	96.21%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.56%	95.83%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.24%	97.36%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.73%	96.61%

Plants that contains it

• Achillea clypeolata
• Athanasia crithmifolia
• Berberis julianae
• Bridelia ferruginea
• Bystropogon origanifolius
• Cardamine heptaphylla
• Centella asiatica
• Cerbera odollam
• Cneorum pulverulentum
• Codonocarpus attenuatus
• Crateva magna
• Diospyros verrucosa
• Euonymus nanoides
• Jacobaea subalpina
• Nepeta multifida
• Pleogyne australis
• Polygala amara
• Pyrola decorata
• Quercus serrata
• Rubus allegheniensis
• Salvia abrotanoides
• Stephania sutchuenensis
• Swertia japonica
• Tetraneuris acaulis
• Unonopsis glaucopetala
• Zieria smithii

Cross-Links

• PubChem: 101140416
• NPASS: NPC258892
• LOTUS: LTS0233090
• wikiData: Q105134527