Olean-12-ene-23,28-dioic acid, 3-(beta-D-glucopyranuronosyloxy)-2-hydroxy-, 28-(O-beta-D-xylopyranosyl-(1-->4)-O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-alpha-L-arabinopyranosyl) ester, (2beta,3beta,4alpha)-

Details

• Internal ID: 61c7ba09-3aa0-4b1d-a5e3-0533ce30a3be
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(2S,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4-carboxy-8a-[(2S,3R,4S,5S)-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxycarbonyl-2-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC(=O)C34CCC(CC3C5=CCC6C(C5(CC4)C)(CCC7C6(CC(C(C7(C)C(=O)O)OC8C(C(C(C(O8)C(=O)O)O)O)O)O)C)C)(C)C)O)O)O)O)OC9C(C(C(CO9)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]2OC(=O)[C@@]34CC[C@@]5(C(=CC[C@H]6[C@]5(CC[C@@H]7[C@@]6(C[C@@H]([C@@H]([C@@]7(C)C(=O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)C(=O)O)O)O)O)O)C)C)[C@@H]3CC(CC4)(C)C)C)O)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O
• InChI: InChI=1S/C52H80O24/c1-20-36(72-41-33(61)28(56)24(54)18-69-41)32(60)35(63)42(71-20)74-38-29(57)25(55)19-70-44(38)76-46(68)52-14-12-47(2,3)16-22(52)21-8-9-26-48(4)17-23(53)39(75-43-34(62)30(58)31(59)37(73-43)40(64)65)51(7,45(66)67)27(48)10-11-50(26,6)49(21,5)13-15-52/h8,20,22-39,41-44,53-63H,9-19H2,1-7H3,(H,64,65)(H,66,67)/t20-,22-,23-,24+,25-,26+,27+,28-,29-,30-,31-,32-,33+,34+,35+,36-,37-,38+,39-,41-,42-,43-,44-,48+,49+,50+,51-,52-/m0/s1
• InChI Key: RPWKGRUCXRZSSG-AORISXJYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₀O₂₄
• Molecular Weight: 1089.20 g/mol
• Exact Mass: 1088.50395341 g/mol
• Topological Polar Surface Area (TPSA): 388.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.60
• H-Bond Acceptor: 22
• H-Bond Donor: 13
• Rotatable Bonds: 10

Synonyms

• 128192-15-4
• DTXSID601099551
• 28-(O-beta-D-Xylopyranosyl-(1-->4)-O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-alpha-L-arabinopyranosyl) (2beta,3beta,4alpha)-3-(beta-D-glucopyranuronosyloxy)-2-hydroxyolean-12-ene-23,28-dioate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8225	82.25%
Caco-2	-	0.8751	87.51%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8714	87.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7946	79.46%
OATP1B3 inhibitior	-	0.2615	26.15%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5276	52.76%
BSEP inhibitior	+	0.8896	88.96%
P-glycoprotein inhibitior	+	0.7464	74.64%
P-glycoprotein substrate	+	0.5142	51.42%
CYP3A4 substrate	+	0.7230	72.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8786	87.86%
CYP3A4 inhibition	-	0.9163	91.63%
CYP2C9 inhibition	-	0.8819	88.19%
CYP2C19 inhibition	-	0.9253	92.53%
CYP2D6 inhibition	-	0.9443	94.43%
CYP1A2 inhibition	-	0.9012	90.12%
CYP2C8 inhibition	+	0.7702	77.02%
CYP inhibitory promiscuity	-	0.9829	98.29%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5774	57.74%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9000	90.00%
Skin irritation	-	0.5887	58.87%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7534	75.34%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8686	86.86%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.7958	79.58%
Acute Oral Toxicity (c)	III	0.6362	63.62%
Estrogen receptor binding	+	0.7773	77.73%
Androgen receptor binding	+	0.7478	74.78%
Thyroid receptor binding	+	0.5857	58.57%
Glucocorticoid receptor binding	+	0.7800	78.00%
Aromatase binding	+	0.6256	62.56%
PPAR gamma	+	0.8249	82.49%
Honey bee toxicity	-	0.6943	69.43%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9756	97.56%

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	99.08%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	96.21%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.09%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.41%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.87%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.23%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.86%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	87.92%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.77%	93.00%
CHEMBL4302	P08183	P-glycoprotein 1	86.31%	92.98%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.05%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.40%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.09%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.59%	99.23%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	82.55%	95.17%
CHEMBL5028	O14672	ADAM10	82.16%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.88%	91.07%
CHEMBL2581	P07339	Cathepsin D	80.66%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	80.38%	90.17%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	80.12%	87.67%

Plants that contains it

• Medicago arborea
• Medicago truncatula

Cross-Links

• PubChem: 101385776
• LOTUS: LTS0046897
• wikiData: Q105243086