3beta-[2-O,4-O-Di(beta-D-glucopyranosyl)-6-O-methyl-6-oxo-beta-D-glucopyranosyloxy]oleana-12-ene-16alpha,21beta,22alpha,24,28-pentol 21-[(E)-2-methyl-2-butenoate]28-acetate

Details

• Internal ID: 8b3f37a7-5aa4-48a3-9d18-875b8ef38b8c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: methyl (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8a-(acetyloxymethyl)-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(E)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxane-2-carboxylate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)CO)OC6C(C(C(C(O6)C(=O)OC)OC7C(C(C(C(O7)CO)O)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)COC(=O)C)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1[C@@H]([C@@]2([C@@H](C[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H]([C@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)[C@@H]2CC1(C)C)C)O)COC(=O)C)O
• InChI: InChI=1S/C56H88O24/c1-11-24(2)46(70)80-45-44(69)56(23-73-25(3)60)27(18-51(45,4)5)26-12-13-31-52(6)16-15-33(53(7,22-59)30(52)14-17-54(31,8)55(26,9)19-32(56)61)76-50-42(78-49-39(67)37(65)35(63)29(21-58)75-49)40(68)41(43(79-50)47(71)72-10)77-48-38(66)36(64)34(62)28(20-57)74-48/h11-12,27-45,48-50,57-59,61-69H,13-23H2,1-10H3/b24-11+/t27-,28+,29+,30+,31+,32+,33-,34+,35+,36-,37-,38+,39+,40-,41-,42+,43-,44-,45-,48-,49-,50+,52-,53+,54+,55+,56-/m0/s1
• InChI Key: RGTNKIXWAOWJPX-PGBOWDDKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₆H₈₈O₂₄
• Molecular Weight: 1145.30 g/mol
• Exact Mass: 1144.56655367 g/mol
• Topological Polar Surface Area (TPSA): 377.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -1.23
• H-Bond Acceptor: 24
• H-Bond Donor: 12
• Rotatable Bonds: 14

Synonyms

• DTXSID401098214
• 254896-70-3
• 3beta-[2-O,4-O-Di(beta-D-glucopyranosyl)-6-O-methyl-6-oxo-beta-D-glucopyranosyloxy]oleana-12-ene-16alpha,21beta,22alpha,24,28-pentol 21-[(E)-2-methyl-2-butenoate]28-acetate
• beta-D-Glucopyranosiduronic acid, (3beta,4beta,16alpha,21beta,22alpha)-28-(acetyloxy)-16,22,23-trihydroxy-21-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]olean-12-en-3-yl O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->4)]-, methyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7524	75.24%
Caco-2	-	0.8674	86.74%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8446	84.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7986	79.86%
OATP1B3 inhibitior	-	0.3173	31.73%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9648	96.48%
P-glycoprotein inhibitior	+	0.7474	74.74%
P-glycoprotein substrate	+	0.6217	62.17%
CYP3A4 substrate	+	0.7477	74.77%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.8973	89.73%
CYP3A4 inhibition	-	0.8504	85.04%
CYP2C9 inhibition	-	0.8702	87.02%
CYP2C19 inhibition	-	0.9017	90.17%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.9011	90.11%
CYP2C8 inhibition	+	0.8021	80.21%
CYP inhibitory promiscuity	-	0.9771	97.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5934	59.34%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.8987	89.87%
Skin irritation	-	0.6306	63.06%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.6878	68.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7570	75.70%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7198	71.98%
skin sensitisation	-	0.8954	89.54%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.8138	81.38%
Acute Oral Toxicity (c)	III	0.7499	74.99%
Estrogen receptor binding	+	0.7296	72.96%
Androgen receptor binding	+	0.7592	75.92%
Thyroid receptor binding	+	0.6223	62.23%
Glucocorticoid receptor binding	+	0.8004	80.04%
Aromatase binding	+	0.6561	65.61%
PPAR gamma	+	0.8081	80.81%
Honey bee toxicity	-	0.6179	61.79%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9235	92.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	98.44%	91.65%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.92%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.25%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.81%	96.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	91.37%	94.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.95%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.43%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	90.01%	90.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.52%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.76%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.78%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	86.49%	94.73%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.37%	91.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.31%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.25%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	86.08%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.06%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.23%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.61%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.41%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.13%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.35%	96.90%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	83.12%	97.47%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.83%	92.62%
CHEMBL5028	O14672	ADAM10	82.75%	97.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.13%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.74%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.25%	93.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.96%	95.50%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.82%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.57%	92.50%

Plants that contains it

• Aesculus chinensis

Cross-Links

• PubChem: 11804359
• NPASS: NPC1314
• ChEMBL: CHEMBL3357146