beta-D-Glucopyranosiduronic acid, (3beta,4beta,22beta)-22-[(2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-beta-D-galactopyranosyl-(1-->2)-

Details

• Internal ID: 89bd8f77-75e4-4d53-aa5c-0ec67f8c5369
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4CCC5(C(C4(C)CO)CCC6(C5CC=C7C6(CCC8(C7CC(CC8OC9C(C(C(C(O9)CO)O)O)OC1C(C(C(C(O1)CO)O)O)O)(C)C)C)C)C)C)C(=O)O)O)O)CO)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]2O[C@@H]3[C@H]([C@@H]([C@H](O[C@H]3O[C@H]4CC[C@]5([C@H]([C@@]4(C)CO)CC[C@@]6([C@@H]5CC=C7[C@]6(CC[C@@]8([C@H]7CC(C[C@H]8O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)(C)C)C)C)C)C)C(=O)O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C60H98O28/c1-23-33(65)37(69)43(75)50(79-23)86-47-40(72)36(68)28(21-63)82-53(47)88-48-42(74)41(73)45(49(77)78)85-54(48)83-31-12-13-57(5)29(58(31,6)22-64)11-14-60(8)30(57)10-9-24-25-17-55(2,3)18-32(56(25,4)15-16-59(24,60)7)84-52-46(39(71)35(67)27(20-62)81-52)87-51-44(76)38(70)34(66)26(19-61)80-51/h9,23,25-48,50-54,61-76H,10-22H2,1-8H3,(H,77,78)/t23-,25-,26+,27+,28+,29+,30+,31-,32+,33-,34+,35+,36-,37+,38-,39-,40-,41-,42-,43+,44+,45-,46+,47+,48+,50-,51-,52-,53-,54+,56+,57-,58+,59+,60+/m0/s1
• InChI Key: OGJALRFDUFLIDX-ZHAZELLBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₀H₉₈O₂₈
• Molecular Weight: 1267.40 g/mol
• Exact Mass: 1266.62446247 g/mol
• Topological Polar Surface Area (TPSA): 453.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -3.65
• H-Bond Acceptor: 27
• H-Bond Donor: 17
• Rotatable Bonds: 15

Synonyms

• 130444-08-5
• beta-D-Glucopyranosiduronic acid, (3beta,4beta,22beta)-22-[(2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-beta-D-galactopyranosyl-(1-->2)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7499	74.99%
Caco-2	-	0.8851	88.51%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8758	87.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8389	83.89%
OATP1B3 inhibitior	-	0.5977	59.77%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	+	0.8756	87.56%
P-glycoprotein inhibitior	+	0.7456	74.56%
P-glycoprotein substrate	-	0.7096	70.96%
CYP3A4 substrate	+	0.7134	71.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.9589	95.89%
CYP2C9 inhibition	-	0.8763	87.63%
CYP2C19 inhibition	-	0.9003	90.03%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.8671	86.71%
CYP2C8 inhibition	+	0.7288	72.88%
CYP inhibitory promiscuity	-	0.9423	94.23%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6313	63.13%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8991	89.91%
Skin irritation	-	0.6520	65.20%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7798	77.98%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8940	89.40%
Respiratory toxicity	-	0.7444	74.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.8349	83.49%
Acute Oral Toxicity (c)	III	0.7822	78.22%
Estrogen receptor binding	+	0.7720	77.20%
Androgen receptor binding	+	0.7448	74.48%
Thyroid receptor binding	+	0.5921	59.21%
Glucocorticoid receptor binding	+	0.7795	77.95%
Aromatase binding	+	0.6779	67.79%
PPAR gamma	+	0.8195	81.95%
Honey bee toxicity	-	0.7165	71.65%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9603	96.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3714130	P46095	G-protein coupled receptor 6	97.71%	97.36%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.98%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.67%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.82%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.63%	93.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.17%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	87.15%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.72%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.57%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.48%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.29%	99.17%
CHEMBL2581	P07339	Cathepsin D	82.85%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.84%	97.25%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.29%	95.50%
CHEMBL5028	O14672	ADAM10	80.92%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	80.29%	92.50%

Plants that contains it

• Trifolium alexandrinum
• Trifolium resupinatum

Cross-Links

• PubChem: 101035652
• LOTUS: LTS0060643
• wikiData: Q105191643